First Dating for the First Time
July 9, 2009 2:37 PM   Subscribe

Please describe the best and/or the worst first date you've ever gone on.

Short version of the backstory: The bulk of my prior relationships have begun from some variant of the "hook up at a bar/party and continue to see each other" method. Right now, things are progressing in such a way that I shall soon get to plan a proper "first date" with a really interesting woman. I'm excited but also nervous, as I haven't a lot of experience with such planning.

I like to gather a lot of information before making a major move such as this. Socializing is kind of a struggle for me, and I find anecdotal evidence quite helpful when trying to solve the riddles of human behavior and interaction.

So, if you're comfortable sharing them, I'd like to hear your stories of the highs and the lows in your first-dating careers. I'm hoping to gather enough of them that I might spot trends and common threads in both the good and the bad, then bring that knowledge to bear when I plan this upcoming evening.

Thanks for your time and your tales - I realize this probably sounds a little silly to the more experienced among you, but for me, nothing dispells anxiety better than knowledge and preparation.
posted by EatTheWeek to Human Relations (60 answers total) 67 users marked this as a favorite
I think there'll be some really interesting stories told, but you'll have to pick and choose the ones that make sense to your situation. Taking someone on a first date to see the sun set from the top of the Empire State Bldg is great, unless either one of you is afraid of heights.

In generic terms, do things that are comfortable and exciting, by turns. Maybe start comfortable then build things up. I'll leave the comfortable and exciting categories up to others.

I didn't tell my stories because there were no first dates: I happened to find that hanging out with an awesome person could build up without the structure of a date. I'm not sure if I'm lucky or not.
posted by filthy light thief at 2:43 PM on July 9, 2009

Go watch back episodes of How I Met Your Mother. They're chock-full of great (and stupid) date ideas. I recommend against stealing blue french horns, though.
posted by Happydaz at 2:45 PM on July 9, 2009

I threw up and she got a speeding ticket.
And the art sculpture we went to see was half dissembled for cleaning purposes.

But, seeing as how we were great friends for years before we started dating, we still had a really fun time. I think that's the most important thing - it seems to me that many people have "friends", and they have "people they date", and the two groups never intersect.
I'm not saying that you should date all your friends, but I think it's very worth it to get to someone fairly well before you start dating. Note that one usually doesn't get to that stage by hooking up at a party. [NOT-PARTYIST]
posted by niles at 2:46 PM on July 9, 2009 [3 favorites]

Best first date:
Relatively blind date. I had no idea what we were going to be doing. Drove 3 hours. Got slightly lost. Met in a parking lot for an antique store/flea market. Got in the same car to make things easier.
Drove 1 minute and went for a short hike along quechee gorge. Talked. walked around some more.
Drove 10 minutes to Woodstock and ate some lunch at a nice cafe. Decent food. Better conversation.
Drove 5 minutes to Simon Pierce and watched them glass blow and make pottery. Once again, short duration, lots of chatter. Nice conversation flow.
Drove 5 minutes back to where my car was. Got ice cream. Talked. Looked at some antiques. Ate ice cream. Drove 3 hours home.

The whole date was maybe 4 hours with 4 distinct. locations and activities. Everything flowed. Nothing was reservation dependant. There was time for conversation if things went well, and there were activities if conversation was at a low or had things not gone well. Plus, with very little knowledge of what we were going to be doing, had it gone poorly from her perspective, she could have cut our activities short after lunch or after Simon Pierce.

We'll go further: Light hike/sightsee - free. Lunch - out 10 bucks if dutch, 20 if paying (which I did). Simon Pierce (is a glass / pottery shop and restaurant as well as having craftsman demo how their products are made) was free, but could have been dinner or a bit of memorabelia. Ice cream is out 4 bucks if dutch or 8 bucks if paying (which I think I did). So conversation friendly, multiple light activities, relatively cheap while each person figures out payment expectations of the other party, no drinking.
posted by Nanukthedog at 2:57 PM on July 9, 2009 [1 favorite]

We went out for Italian. I ordered ravioli in some kind of red sauce, and rather than stabbing the ravioli with my fork, I scooped it up.

The ravioli slipped off and splashed into the sauce below. Our table was huge (disconcertingly so, for a first date), so as a joke as I was looking up, I laughed and said "did I get any on you?" because the idea was patently ridiculous.

I was wrong; the sauce was all over her white, silk blouse. The date went downhill from there (but that was a good thing, I didn't like her anyway). Never talked to her again!
posted by pkphy39 at 3:03 PM on July 9, 2009 [1 favorite]

My first date with my wife involved beer and lesbian porn. For some reason, she gave me another date, and for some other reason she married me.

All's well that ends well, I suppose.
posted by elder18 at 3:12 PM on July 9, 2009 [4 favorites]

Worst: Met a guy from Yahoo Personals in a bar. He didn't offer to buy my drink. Someone called his cell phone and he answered it "Hey, baby" He then went outside to take the call and spent 15 minutes talking to the person. He had no explanation when he came back in. I left.

Best: This will sound contrived, but it's actually my first date with my husband, because although we didn't do anything spectacular (standard movie-and-dinner date), I felt really comfortable with him. The bestest part was when he told me that he'd told his mother how excited he was to meet me (we'd met online a few weeks prior).
posted by desjardins at 3:12 PM on July 9, 2009

I had a date that progressed from dinner with wine, to a show with drinks, to me thinking I'm dropping her off only to have her say "Get in my car" and grabbing a six pack and some cd's, to her daring me to hit that sign with a beer bottle to her getting pulled over and getting a DWI.

I showed up in the morning with the bail money, but we never talked again.
posted by notsnot at 3:17 PM on July 9, 2009 [6 favorites]

Bad: After dinner we went to a park with some friends (double date). She and I were cited for drinking beer in said park, and the police were ever so good at making her think that she had just committed a heinous crime (we were both young and scared).

Extra bonus - I met my future mother-in-law, for the first time, at the court date.

Good: Almost 18 years later, we're still happily married.
posted by doh ray mii at 3:18 PM on July 9, 2009 [1 favorite]

My favorite First Date story...

I'd recently moved from Houston to Portland, and I was on a first date. I mentioned to the woman that I was new to the area, and that I'd never been to the Pacific Ocean. This was small talk really. I was simply making conversation... talking about how much I enjoyed this part of the country, and the many things I looked forward to doing here someday... when all of a sudden, the woman who'd been ultra-shy thus far into the date takes initiative.

The next thing I knew, we were headed to the coast. I know it's a bad idea, but we're already in her car.

Keep in mind that I'd been in Oregon a few weeks at that point & didn't even know WHERE the coast was - byond the basic "yo, it's over that way." The drive could have been ten minutes or ten hours... I had no clue. It turned out to be an hour and a half... which was an hour and 29 minutes longer than I needed to piss this woman off.

Shortly after we left Portland, she said she has a bizarre family. OK. I've got to tell you... NOBODY in their right mind wants to go toe-to-toe with me on the age old battle of who's family is more half whacked because mine is fully whacked. I'll win. Not sometimes... I'll win every time. Am I proud of this? No. But there's no sense in living in denial. It is what it is.

Who's family is nuttier? The game goes like this: You tell me that your mom is addicted to Prozac, I say that some uncle I'd never met tried to kidnap me on the day of my father's funeral when I was 11.

This time, I didn't even pursue the debate. I started her off with a tough one to top: I told her my grandmother was born in an Italian prison (true). And then SHE told ME her brother borrowed her mother's car and got into an accident.

...with a cow.

Well now come on... I need the rest of THAT story.

I asked: "Why was he driving her car in a field?"
"He wasn't"
"Well where was he?"
"On the road someplace."
"And there was a cow?"
"I guess"
"Well didn't he say?"
"I don't know..."
"What do you mean?"
"Oh, he's always getting into trouble."
"But he hit a cow"
"Well yeah"

...Blank stare.

It dawned on me that I was starting to bug her. (gee, ya think?) And even worse, I was probably disparaging her brother too. Tension mounts.

Quick thinking! ("I know! Maybe it wasn't her brother's fault.")

"Maybe it wasn't his fault." (ohgod, I said it out loud)
"What do you mean?" she asked.
"Well... maybe the cow was at fault." (as if saying it again made it better)

...blank stare...

I then began to think up car-meets-cow scenarios in which the cow is to blame. I asked questions like:
- Was the cow tailing him?
- Did the cow fail to signal?
- Did the cow run a red light?

You'd think I'd have the common sense to shut the hell up. But no...

"Was the cow passing on the inside?"
...blank stare.

"OH! I've got it! When two cars come to a 4 way stop at the same time, generally speaking, the car to the right has right of way... but there's really no protocol for a car and a cow at a four way stop. Maybe they both panicked... they both went for it, and wham!"

...blank stare...

"Well is this even a right of way state?"

Realizing that's about as dumb a question as I could have asked, I decided to shut up.

We drove along silently for a few minutes... ...but then.

I Giggled.

She said "WHAT!?!"
"Well.... I'm just curious..."
"Was the cow at least insured?"
"Well I figure a cow probably has Farmers... or maybe State Farm... right?"


"No more cow jokes."


Thank god we finally reached the coast. Seaside Oregon turned out to be an adorable little town. The date had taken a turn for the better! (she was talking to me again after all)

On the way home, she asked if I'd ming stopping by her mother's place so she could pick something up. There's no polite way for a guy to say no in a situation like that... so...

We entered her mother's house.

Of course her whole family was there. Extended family included. She'd previously mentioned the upcoming date to her mother, which meant the entire west coast had been informed. The sound of 'Ooh' filled the house as I walked in.

Her mother loomed... "How was your dayyyyte?" (hello! I'm standing RIGHT HERE)
She replied: "He was making cow jokes." (again - I'M - RIGHT - HERE)

The crowd of family members turned to look at me. "Cow jokes?" someone asked, and it dawned on me that they might think I was referring to her.

"Well, she told me that your son borrowed your car and hit a cow."

People giggled as if they thought that was funny too... because it really was funny... Then, there was a long silence... so...

I proceeded to tell the entire story from the beginning. All of it. These people were turning the most amazing shades of pink, red and purple because they were laughing so hard... And, best of all, my date was laughing too. Well looky there, I made her smile after all.

She's a good friend to this very day, and she hates when I tell that story - but it's toooooo funny not to tell.
posted by 2oh1 at 3:26 PM on July 9, 2009 [45 favorites]

Came in to meet parents, who had just gotten new car, showed me said car, noted that car had most options except power windows, was informed that power windows might not work in a flash flood, laughed at assumed joke and commented on the odds of that happening to some idiot, was informed this had recently taken the life of beloved sister.
posted by Cosine at 3:27 PM on July 9, 2009

"The bestest part was when he told me that he'd told his mother how excited he was to meet me "

That doesn't seem like a good thing to say...but am I wrong?
posted by Groovytimes at 3:27 PM on July 9, 2009

When I was in college, my roommate set up a double date for me with a girl who I knew only a little; she had a class with me. Roomie and his girlfriend were the other component of the double date. The girl in question apparently found me "cute."

On the day of the date, my roommate and I were driving around to get some lunch, and I said I was looking forward to the evening. He then said, "Yeah, so is Holly [not her real name]. She's been pretty down since she found out her last boyfriend gave her genital warts."

That was a long night for me.
posted by Skot at 3:29 PM on July 9, 2009 [6 favorites]

Bad: With I guy I'd met at work (but we worked in different buildings, so it seemed OK) who'd asked me out after several pleasant chats. His idea of a date - took me out for dinner, then parked on a dark side street, produced a hash pipe (we'd never discussed drugs prior to this moment; he just presumed I'd be up for it) and wanted to make out. I backed out not-too-gracefully by looking at my watch and saying "Wow, look at the time, I really should be getting home...."

Good: The man I eventually married took me to a very elegant Italian restaurant for our first date. He didn't even live in the same state as me at the time, but had taken the time to do some research and found this very lovely place (we both loved Italian food). Afterward, I suggested going to a small bar I'd been to a few times years ago with friends called the Irish Coffee Pub. It specialized in coffee drinks - coffee with Kahlua, or Irish whiskey, or Amaretto....topped with whipped cream. We sat and talked for hours, and discovered many oldies on the jukebox that prompted us both to say "I haven't heard this song in years - I love this song!" We got pleasantly relaxed but not drunk after many coffee drinks, and the old songs prompted a discussion that rambled from favorite childhood toys, to current favorite board games and TV shows, to embarrassing things that had happened to us in the past. A wonderful, fun, relaxing evening.
posted by Oriole Adams at 3:32 PM on July 9, 2009 [2 favorites]

Best first date: He picked me up, we went to a (somewhat nice) restaurant and had dinner and talked. Then we went from there to an exhibit sponsored by the Smithsonian at a local art museum. It was several different kinds of art, and we had fun discussing what we liked and didn't like. We kissed on the balcony overlooking the Mississippi. Then we went to my favorite ice cream parlor and had ice cream. After that, we went back to his place and watched Pan's Labyrinth.

It was a really nice date. We had only planned dinner and the art museum, but neither of us wanted the date to end, so we fabricated some more things to do, and it was a lot of fun. I do NOT recommend dinner and a movie just because sitting in the dark with someone for 2 hours doesn't let you get to know them very well. A play or the opera would be better than a movie because circumstances are more conducive to whispering. Still, though, I wouldn't want to have a first date where more than half of it didn't involve interacting with the other person.
posted by Night_owl at 3:36 PM on July 9, 2009

Best first date that led to a two year relationship: he did all the planning, said it would be a surprise, all I did was dress up and show up. He picked me up after work, we went out to dinner, we went for a walk, decided to grab a brownie sundae at a random diner (impromptu), and he drove me back to my car. That restaurant, that diner and brownie sundaes became special to our relationship. To break it down, what made it a great date was:

1) Dressing up was fun for me, and my personality is such that I liked the suspense of not knowing where we would be going.

2) He did all the planning and left no confusion as to who would be paying. I would have been happy to split dinner though. The restaurant was also perfect -- nice without being intimidating or stuffy, and good noise level so we could hear each other, but good ambient noise level in background to fill in quiet moments / enjoy the great food and wine.

3) He called to confirm and expressed that he was excited about the date. That was a good move since we were both nervous, and that call transformed the nervousness to (more) excitement.

4) It wasn't really about the brownie sundae, we were just having such a good time we wanted to draw the date out a bit more; that felt great.

Worst first date: actually remarkably similar to best first date. We set a date and time, he planned dinner, I dressed up, we took a cab to the restaurant together, had a nice meal, he clearly blanched a little at the total so I offered to split the bill, which I really was fine with, but he made it really awkward. We dated anyway on and off for a few months.

Really, the big difference was chemistry - I had a lot in common with the first guy and we had a deep connection; his planning helped to calm the usual first date jitters. I also liked the second guy, but on a more superficial level; we subsequently went on some of the best dates I've ever gone on when he was much less nervous.

Incidentally, none of my examples are of my current boyfriend (going on 4 years) because we hardly ever go on real dates. I once saw a book called "best non-dates" or "best cheap dates" or something and laughed out loud because it desribed us so well. So, I guess I am saying don't be nervous, planning / setting expectations can help with the anxiety, and if you already enjoy her company, I am sure it will go well!

p.s. Don't bring her flowers unless you're picking her up at home -- it would be really awkward to carry flowers to a restaurant. That's just about the only time I can think of when I would not want to receive flowers. Good luck!
posted by booksandwine at 3:37 PM on July 9, 2009 [1 favorite]

A P.S. to my story above:

I've found that the best first dates tend to revolve around an activity with some sort of time-out for sitting and talking. A walk around town followed by happy hour at a pub... or meeting for a drink and a silly board game. It may sound odd, but it really works because there's something to do, plus time for chit chat and flirting.

My worst first dates were when we went to see a movie (no time to talk, so it tends to be a short date, excluding the time watching the film). Also, dinner dates are recipes for disaster since you're stuck with someone for the duration of a meal rather than just for a drink, and there's a lot of time when you can't talk because you're eating, which just leads to a lot of awkwardness.
posted by 2oh1 at 3:37 PM on July 9, 2009 [2 favorites]

Best first date - a trip to the omnimax theater at the local science museum, followed by dinner and making out in a tree.

Worst first date - I met this guy on a forum once, and agreed to meet up with him for coffee, mainly because I thought his job was really neat (something with nanobots, if I remember correctly). Over coffee, I said: "Tell me about your job!" Him: "Oh, I hate it." Me: "Oh, well... what do you do outside of work, then?" Him: "Play around on my computer." I tried to change the topic and tell him about my roommates' new puppy. Him: "Oh, I don't really like dogs."

Take-away lesson? Don't be a downer. Also: imax films rock.
posted by shaun uh at 3:45 PM on July 9, 2009 [2 favorites]

As far as drinking goes, if you're planning on that, try and apply the company party rule of having one drink, max. Being drunk is not a good way to impress or get to know someone.

Personally, I'd find it a bit insulting if someone went on a date with me and got smashed. As others mentioned, the more opportunity you have to talk to a person, the more both of you will know if you like each other. Even if you're nervous, she will be too, so just dive right in.

Good luck!
posted by elder18 at 3:45 PM on July 9, 2009

Unknowingly managed to crash a invited only showing at big auction house. Lots of great art, free champagne and canap├ęs.
posted by uandt at 3:46 PM on July 9, 2009

The best dates I've had involved partaking in a shared activity that we both liked, and then spending the rest of the evening talking about the experience and whatever conversational tangents ensued. Could be a movie, art gallery, trip to a bookstore.... go with a shared interest. You'll have something to talk about and when things go well it can lead you into that conversation you share for the rest of your life.
posted by Billegible at 3:52 PM on July 9, 2009 [1 favorite]

My first date, literally my first date, I took the girl of my teenage dreams to the movies, a romantic comedy. Turns out watching people go through the pitfalls of starting a relationship is not a good way to start a relationship.

My first date with my wife we met at a nice cozy pub that didn't play loud music and talked for hours about everything and anything. That one worked out pretty good.
posted by IanMorr at 3:57 PM on July 9, 2009

Worst: I'm relatively tall, so friend fixed me up with a man a whole foot taller than me not realizing that men much over 6' make me nervous. 6'8" had me positively twitchy.
Other worst: Friend fixed me up with a dental student, and I'm terrified of dentists, even nice lady dentists. Might as well have fixed me up with Cobraman as told me all about dental procedures during dinner.

Best: We met at the restaurant, fended off the loudest, nosiest collegue we worked with who just happened to stumble in for a drink, and drove home in a blizzard the weatherman forgot to mention was coming. Somehow, shared adversity made it fun. He's still here all these years later.
posted by x46 at 4:08 PM on July 9, 2009

My worst first date ever ended up with me bleeding from the nose, on my hands and knees crying "But the internet told me this was a good idea!"

My best first date ever, we went to an Omar Faruk Tekbilek show, drank, and made out.
posted by turgid dahlia at 4:13 PM on July 9, 2009 [1 favorite]

Worst: A guy invited me over to his place for dinner. I show up and the place is an absolute dump- he lived in the basement storage facility of a large building with four other people and a feral cat. It should have been condemned. Then, for dinner, he boiled up some pasta and dumped on a jar of sauce. And that was it- no salad, no bread, no wine. Nice guy, just totally clueless!

Best: Went to get pizzas and beers a cute local Italian joint. Turns out it's trivia night, and my date's elderly trivia-obsessed uncle is sitting at the bar (pure coincidence). The uncle ended up joining us for pizza and we won the trivia contest. Then my date and I drank a bunch of beers and chatted. It was a perfect low-key get to actually know someone first date.
posted by emd3737 at 4:14 PM on July 9, 2009

Worst - any sort of party/bar situation. it's awkward and you never get to really talk to the person because it's so loud and there are so many other people around.

Best - with my current boyfriend. we had been talking online for a few weeks (mutual friends) and one morning, he showed up at my door and swept me away on a day trip to cincinnati, about 3 hours from where we lived at the time. it was the perfect first date - the weather was nice even though it was winter, we playfully argued over mix cds and compared cd collections on the way there/back, and we just walked around a city where hardly anyone knew us, stumbling over street curbs and kissing foolishly on every corner, pretending we had been together for years and years. we met up for drinks/dinner with an old high school friend of mine that night and he asked us how long we had been together. it was kind of awkward when we said, "8 hours" but also very sweet in that new-love way. he's been sweeping me away ever since.
posted by kerning at 4:30 PM on July 9, 2009 [2 favorites]

Was set up on blind date by a friend, he met me, said he had to stop by his house to drop something off to a friend, the 'something' was drugs, found out he was a small time dealer, couldn't figure out how to get out of dinner with him so sat through it where I was informed I was the spitting image of his ex-girlfriend who was a heroin addict. He proceeded to scope me out on my views of marriage and kids while getting hammered. Then offered to drive me home (drunk). Wouldn't let me drive. I (stupidly) got in the car with him anyway. When we pulled up to my house he then tried to kiss me and ask when we could go out again, then called me repeatedly after that. Why yes, that was my worst date, why do you ask? In my defense, I was only 18 which is why I was too freaked out to just get up and leave.

My best first date was at an outdoor cinema. He bought chicken salad, a bottle of wine and a picnic blanket and we sat under the stars and watched a movie. We talked for hours. Four days later I flew up to Singapore to look for work and he came too and we both stayed with mutual friends. He must have thought it was his last chance to get to know me if I was moving to another country. Following me up there was a pretty big gesture seeing as we'd only been out once but I guess it worked out pretty well though, we got married in January...
posted by Jubey at 4:41 PM on July 9, 2009 [3 favorites]

I'm excited but also nervous, as I haven't a lot of experience with such planning.

Don't worry about the planning, have fun, and don't take dates that don't work out personally. It's really just down to chemistry, and what you do doesn't matter all that much. A poorly-planned date with the right person will be better than a perfectly-planned date with someone that's not a good fit.

Dinner and an activity where you interact is good. Bowling, roller skating, going to a museum, etc. A meal is good because you can see how they treat wait staff; if they're a jerk to them, they're a jerk. A movie is usually not so good because you don't interact.

Worst: internet date, first meeting for coffee and a movie (which we'd mutually agreed sounded interesting).

We got coffee and sat at a two-top table, and she wouldn't look at me. I mean, she sat across the table and positioned herself at a 45-degree angle and looked that way instead of making eye contact. It was so staggeringly rude and socially inept that I wasn't even upset because I was already anticipating the pleasure I was going to get from telling the story about the date. We talked, but it's weird talking to someone who won't look at you.

For some reason we went to the movie, which turned out to be too sedately paced for her, and she made her displeasure known to me and our neighbors with audible sighing and dramatic eye-rolling. She popped up out of her seat the instant the movie ended but there was no goddamn way we were leaving until the credits finished, and I was sitting between her and the aisle so she couldn't do much about it. We said "bye" as we walked out the theater and I laughed all the way home.

Most perplexing: a dinner date with a friend-of-a-friend who I'd met at a party and thought I was cute. We had a nice dinner, stopped to get gas and chat about what to do next, then she started making out with me, which was fine with me. We decided to go to my apartment for more making out, during which she took off her shirt, which was also fine with me. The next day I called her and she said things were moving too fast and that was that.

Most awkward: another internet date. We had hit it off great on the phone, and talked for a couple of hours, then met for coffee and had absolutely no chemistry in person.

Really, just relax and have fun. These seemed like a big deal at the time, but to be honest I don't even remember the actual people, just the stories.

said he had to stop by his house to drop something off to a friend, the 'something' was drugs
That happened to a friend of mine, too.

posted by kirkaracha at 5:00 PM on July 9, 2009 [2 favorites]

Worst first date:

We met through online dating, and went to a bar for drinks and tapas. He spent the entire evening complaining. The drinks were watery. The food was too cold or too hot or not spicy enough or too spicy. Everyone at his work was an idiot. He hated his apartment. He hated the city. He hated the weather.

After two hours of listening to him whine about anything and everything, he walked me home and when I said good night, he responded with "I paid for your drinks and you're not even going to invite me up!".

My response: "What, so you can complain about that too?"

Best first date:

Lunch, then drinks, then a play, then a very late dinner...because neither of us wanted the date to end. He pretty much moved in two weeks later and we got married last summer. It was the cliche of love at first sight, which I never would have believed was real had I not experienced it myself.


It's not about where you go, or what activities you plan for your date. It's all about who you're with.
posted by burntflowers at 5:07 PM on July 9, 2009 [4 favorites]

Hey, you're in Olympia! Why not take a walk around the lake downtown, then grab some lunch at the farmer's market or the Bread Peddler? The paths at Tumwater Falls are also nice (and not too long, either). Other fun places I have been on first/early dates: the nature trails at McLane Creek, followed by dinner at Fujiyama (silly but fun); 3-D glow in the dark mini golf at Shankz; fish tacos and Manhattans at Quality Burrito. Good times.

I've also had a few comically bad first dates that all seemed to happen at Ben Moore's. At least they mix good cocktails.
posted by Vervain at 5:09 PM on July 9, 2009

worst: completely blind date, set up by a "friend" Met at a bar local to her for some drinks (her idea).

She fails to mention that it is $0.25 Keystone Light night, she's been there for 2 hours prior to my arrival, and has already run up a $3.00 tab.

In no short amount of time, it becomes readily apparent that a: we have nothing in common, b: she's really not my type, and c: she's sloppy drunk.

So, there I am, desperate for a polite way out, when the following 2 things happen in rapid succession:

Appropos of nothing, she quite drunkenly offers to take me to the parking lot for some "grilled cheese". Before I can politely decline, she takes note of the music the DJ is playing and says....

"I can't believe they're playing rap music with all these n*ggers here. They usually don't, because they want them to leave.

Suffice it to say, I was taken aback. After picking my jaw up off the floor, I said "gotta hit the restroom" and just left.
posted by namewithoutwords at 5:16 PM on July 9, 2009 [3 favorites]

Didn't happen to me, but to my father.

He had a party trick of setting a shotglass of spirits alight, then blowing it out just as he raised it to his lips to drink.

He lit the drink. People were amazed. He got distracted for a few moments longer than normal. He raised the glass to his lips. He blew out the flame.

Then he touched the searing hot glass to his lips. Alcohol everywhere, skin removal, general uproar.

He didn't have another date with her.
posted by tomble at 5:38 PM on July 9, 2009 [2 favorites]

We were students in the same hotel in Paris. We went out for ice-cream. I went to pay and realized I'd forgotten my wallet (first and last time). I had to go ask her for money to buy the ice-cream. We ate the ice-cream and wandered around Paris hopping on and off the metro.

Second date, I paid. This year we celebrate our 10th wedding anniversary. My wife says she saw the potential in me :o)
posted by arcticseal at 5:54 PM on July 9, 2009

Correction: it was a hostel, we were poor students!
posted by arcticseal at 5:55 PM on July 9, 2009

I've had a fantastic first date with a great guy who got nervous diarrhea an hour into our time together, essentially "ruining" our dinner plans, and I've had a terrible first date with an annoying guy who took me to a restaurant I loved and did/said all the "right" first date stuff. It's all about who you're with, not what you do or even what happens.

That being said, anything involving a little consideration to her interests gets things off to a good start. The great guy with the nervous tummy took me to the beach for a sunset walk because he remembered my saying that I love the beach in the off-season. I gave the annoying guy benefit of the doubt because he'd asked me what type of food I prefer and chose a place I hadn't been before but liked very much.
posted by pammeke at 5:55 PM on July 9, 2009

One of my worst first dates started with a traffic accident that was dragged on for a while by the cops, then we ate at a loud and crowded seafood restaurant that ended up giving me food poisoning, my date accidentally broke one of the heels of my shoes (incidentally a favorite pair), and after dinner we were interrupted by his drunk friend who called desperate for a ride so the night ended with a pukey drunk guy in the backseat.

On the other hand, I'm now engaged to the guy who took me on that date. First dates aren't everything.
posted by lullaby at 6:54 PM on July 9, 2009

We met online, met in person for the first time and saw a movie, then drove around doing nothing but talking and laughing. We spent the entire weekend together. Three months later we eloped, now we have a child and are still going strong. If you can go out, with no formal plans, and have fun together then you have a keeper. You learn more about someone making it up as you go along than if you plan the entire evening.
posted by sporaticgenius at 7:06 PM on July 9, 2009 [1 favorite]

Agreeing with the "it's who, not what" crowd.

Best date: We'd originally planned to walk across the Brooklyn Bridge, but it was raining. On the phone with him, I looked up free stuff going on in the city that night. There was a concert/recital going on at my college, and NYU has a pretty awesome performing arts school, so I was sure that would be a safe bet.

When he met me at my place, it had just stopped raining, so we started walking rather than taking the subway. He had the idea to swing through Little Italy to pick up dinner on the way, which would've been fine, except I'm allergic to tomatoes. After about a mile of walking (and no dinner for me), we wound up being early for the show, so we stopped at a Best Buy to kill time and to pick up a cable he needed.

When we got to the recital, we realized it was a performance by high school students who'd attended a one-week camp at my college. The school might be quality, but one week was not enough to turn those kids around -- most of the performances were varying degrees of awful, with only a handful of standouts. We wrote notes on the program and tried to predict the kids' futures.

Afterwards, we tried to find a park for more private conversation (and, okay, a chance to kiss). On a gorgeous summer evening in the middle of Manhattan, we weren't the only couple with this idea -- we tried four parks, all of which were packed, before eventually settling in the courtyard of an apartment complex. We talked for hours before even getting around to kissing.

That date wound up lasting over 12 hours and 9 miles as we spent the night walking all over New York, totally incapable of shutting up. After we watched the sun rise, he dropped me off in front of my building, giving me a kiss for each hour we'd spent together.

That relationship did not end well, but it was still definitely the best first date I've been on -- even though we had last-minute plans and no clue what we were doing, I didn't get dinner, we went to a terrible show, and walking 9 miles isn't usually my idea of a good time.

Least-good date (I have some outright horror stories, but this isn't one of them -- just a date that should've been fun but wasn't): We met online, and both of our profiles mentioned liking Jeopardy; I think he had also done College Bowl or something and currently attended a weekly trivia night in his neighborhood. We tried to find a trivia night when we were both free, but had no luck, so he suggested a trivia game he knew about at Dave & Buster's.

Dave & Buster's is basically an adult Chuck E. Cheese, so it's obviously not something you can take too seriously. I went full-out juvenile and ordered chicken nuggets, I think. He sneered and ordered some kind of pasta dish; it may have had more ingredients and a more sophisticated name, but I'm sure it was frozen and nuked -- if you're going to D&B's for haute cuisine, you're doing it wrong. Aside from the sneering, he seemed like an okay guy, but conversation was halting.

Later we headed to the trivia machine, which was a pretty decent six-person setup. I was just having fun playing and talking to people, and unfortunately I wasn't paying attention to who was winning. When the tickets started pouring out, I realized way too late that not only had I won, I'd also about doubled his score -- a serious, if inadvertent, asshole move. We moved along to Skee-Bowl and other arcade games, but the damage had been done. The night ended on a pretty chilly note (although my tickets did earn me a rice cooker).

If you looked at the setup alone, you would think it would be a solid date: a chance to get to know each other over dinner, then a fun activity related to a mutual interest. In practice, not so much. The person is almost always more important than the activity. If you get along, it really doesn't matter what you do; if you don't, there's not a lot that can salvage the situation.
posted by booksandlibretti at 7:33 PM on July 9, 2009 [4 favorites]

Worst: I went out to dinner with a guy with whom I was taking a class. We had a reasonably decent time, so we went back to his place to watch a movie. As we're sitting on the couch, his apparently very recent ex-girlfriend knocks on the door and starts a screaming match with him. Helloooo, awkward.

Best: My now husband and I went to the local zoo together. We wandered around, had fun, and saw the gorillas getting it on doggy-style. Also awkward, but funny awkward.
posted by chiababe at 7:45 PM on July 9, 2009

Worst first date was a woman who I absolutely hated for her personality. She described herself as "bossy, but that's just how I am." She considered "wines" to be one of her greatest hobbies, even though I'm pretty sure she just liked to get fucked up. At one point, she ruined a perfectly good conversation about art by saying (with a flip of her hair), "I'm so over art." She waited until after she was at my apartment to mention the horrific case of bedbugs she was dealing with. She went on at great length about her ambien addiction. Everything she said sounded sarcastic, even things that I have no reason to believe were actually sarcastic. And the thing is this -- I disliked her because she was profoundly annoying. If she'd had bad teeth or a skin condition, I'd kinda feel bad for her, like "okay, it's not her fault." But she was just so incredibly annoying, I hated her and I was perfectly okay with that. So this was sorta like the best-worst date ever.

I've had a few first dates where the woman kept asking probing questions about my family long after I made it clear that I didn't want to talk about them. Why do Jewish womans always want to talk about your family on the first date? Totally never going back to J-Date.

Had a few of the typical "goods were not as advertised" online dates, a few stealth fatties, etc. Yeah, it comes with the territory.

My best first dates? You know, it's weird. Because it's just totally random. They all start out the same way -- usually at a quiet-ish bar where conversation can happen -- and sometimes it just works. I've had dates where I was sure it went off great, and then the woman didn't return my emails. I've had dates that I thought were thoroughly typical, but then the woman turns around and sends me a text right after she gets off the train to tell me what a good time she had. As much as I hate to say it, you just have to go with your best instinct and not get bummed when it doesn't work out. Because really, you could do everything right and still get it wrong, or do everything wrong but still she sees something in you.

I dunno, it's nice out this time of year. Maybe go for a picnic or a long walk?
posted by Afroblanco at 7:49 PM on July 9, 2009

best first date:
my date, not knowing whether i would want to go to a movie or get coffee or have dinner, presented me with a bunch of options upon my arrival. i wasn't hungry, and i don't like seeing movies as a first or second date option so i suggested we go for a walk to a coffee shop about 20 minutes away from where we met up. we ended up walking for 4 hours (right out of the city and down to the water!). when we got back to where we started, we did get coffee, but just to prolong the date. so i suppose i fit in with the "it's who, not what" group because we didn't really need to do anything!

worst first date:
dinner with a former co-worker. he wouldn't talk about anything other than work and was rude to the waiter. it was a real shame that my roommate called and i had to go home straight away... a real shame...
posted by gursky at 8:23 PM on July 9, 2009

I might throw in a worst first date story:

This involved a girl who I wasn't even particularly interested in or attracted to, but I'd been going through a bit of a dry spell & was open to giving things a shot to see what might turn out, and so it somehow happened that we went out to see a band "together", amongst a bunch of friends.

Using a meal at the pub bistro as an excuse for some private time, we were still waiting for our food to arrive when apropos of nothing at all, she started off on this line of conversation:

"So, have you ever visited a prostitute?"

"What? No. That idea doesn't really interest me at all"

"I don't believe you. All guys visit prostitutes. You might as well admit it, because I can't go out with you if you're going to lie to me."

"No. I'm not admitting to something I didn't do just to satisfy your demands"

"You probably just visit massage parlours for a rub-n-tug every now and then, and tell yourself that it's not prostitution. Whatever, it's alright, I know you have urges that you need to have satisfied; all guys do"

It went on like that for some time, with me already having decided that this girl obviously had *serious issues* and that I certainly wouldn't be seeing her again.

Then she switched to "Have you ever been with a guy...?" and I was "[oh, no, here we again!] Hey, I think the band is just about to begin; we should go back & join the others..."
posted by UbuRoivas at 8:56 PM on July 9, 2009 [2 favorites]

I went to pub with guy, and we chatted and drank, we went to a park where we kissed for the first time and made out in the jungle gym. We left and went to an all night diner. We talked and talked. I went home when it started to get light out.

Usually, best dates are variation on that. At least for me! Just be relaxed and don't have a set agenda. It's the spontaneity of not going home, and going somewhere else (and tacitly showing the person that you don't want to stop spending time with them, even if the restaurant is closing) that makes it fun and exciting (even if wherever you are is completely ordinary.)
posted by Kololo at 9:42 PM on July 9, 2009

I've already told the story of my worst date in an old thread. You can find it here (second part of the answer). It involves a guy who was so over the top, nauseatingly lovey-dovey, asking when we could get married (on a first date!! A blind date, no less!!), it was difficult to make it through to the end of the night.

My best first date is a lot like lololo's story. We met up in the city to see a film that was part of a foreign film festival. Then we went to dinner at a cool, Burmese restaurant. There was much conversation and flirting as we walked, chatted throughout dinner, it was totally easy, no awkward moments, no super serious getting-to-know-you-in-a-way-that-feels-like-an-interview discussion. Then, as we were heading back to the metro to go our separate directions, we decided to stop for coffee first and ended up laughing and chatting till past 2:00 a.m., and only left then because neither of us was sure about the time of the last train in one direction. It was nice, fun and effortless.
posted by necessitas at 10:19 PM on July 9, 2009

I will spare you the full painful Story of Lipo Guy, and just recommend avoiding restaurants where her ex and his family happen to be dining, and not sharing all the details of your medical history. Especially if that medical history includes liposuction two weeks prior (discount liposuction, no less. He knew a guy who was a plastic surgeon so he got a really good deal on it. I thought it was a joke and laughed out loud and insisted he tell me what kind of surgery he really had and slowly realized IT WASN'T A JOKE.)

Aww, now I want to make out with someone in a tree.
posted by little e at 11:18 PM on July 9, 2009

Worst first date ever:

Guy I met at a club in college asks me out, so we arrange to go to a show my friend's in (me being a big theatre person, him not). The show? Titus Andronicus. Unless you two are both big Shakespeare fans, do not take a first date to see Titus Andronicus. Amazingly, he manages to both be somewhat horrified AND fall asleep at points. This was after getting lost trying to meet each other. Afterward, we go to a university carnival event with my friends, and since I'm nervous and don't know what to say to this guy I have seemingly little in common with and am not particularly attracted to, I behave in bad form and semi-ignore him in favour of talking to them. If you're apt to get nervous around a new date, don't bring people to your date who you are more comfortable with. To cap off the evening, we (including several of my friends) go for coffee in the campus centre. He mentions that they must have put some kind of almond syrup in the coffee by accident, which I think sounds nice, but it turns out he's allergic to it, starts having a reaction, and has to go to the campus health centre (conveniently steps away from the campus centre). We never really spoke to each other again. To this day I wonder if he faked an allergic reaction to get away from me.
posted by ilana at 11:22 PM on July 9, 2009 [3 favorites]

Basic thought: Don't make it A Big Thing in terms of asking or assembling a grand plan. It's just a couple people finding each other interesting and wanting to spend a little time together. That said you're likely better off with some planning, asking, "Would you like to (something specific that's not devoid of thought or imagination and maybe relates to an interest she's mentioned) on (specific time and day)," more than, "Wanna do something some time?"

Worst... and it was surprising. Met online, ended up trading reams of IMs for several days (we both had jobs where we could do this all day), chattering away effortlessly, making each other laugh, each enjoying what the other had to say, having gobs to talk about, some nice compliments from her, I helped her with some work stuff she was trying to figger out.

We met (I was on time; dressed appropriately for the plans; wearing clean, not-wrinkled clothes; had showered and shaved; looked exactly like my posted pics--all the basic stuff) and straight-away she was not real pleasant. Very short answers to my questions about her work, places she'd lived, things and places she enjoyed in the city, No questions from her or comments about... anything.

I asked at one point if she was having a bad day. She said no.

It was strange, like the online person and the in-person person were two different people.

We ate, she went to the toilet, came back, a couple minutes later the phone rang and it (allegedly) was her roomie and some story about how roomie had locked herself out or something like that.

Funny thing was, at the time a local station was showing Sex and the City 'round the time I'd go to bed so I'd watch it for some brain candy, had seen one of the gals (Charlotte?) do exactly that thing--unhappy on date, bathroom, a call and "Oooh, gotta dash."

Couldn't resist saying I'd just seen that on a TV show, there was no need to lie, I had been ready to leave for some time and leaving immediately.
posted by ambient2 at 11:29 PM on July 9, 2009

Worst first date: blind double date through an acquaintance. I meet Rodney. Who proceeds to talk about himself the entire evening. How much his shoes cost. Where he went to school. His last vacation. He's also getting very, very drunk. I'm ready to get out of there, but my friend and her boyfriend (who I have ridden with) have disappeared, leaving me with Rodney. Great. I tell him I'm ready to go and I'd like him to take me back to my car.

On our way out to his car, I tell him he's kinda drunk, and he should let me drive. Rodney then proceeds to deliver a speech I will never forget - he doesn't want a woman driving his car, and in fact, he doesn't think women should be driving at all. I just wanted to go home, so I get into his car (which in retrospect was a bad bad BAD idea and I'm lucky that I survived this).

So we're about three miles up the road and he asks the one question about me the entire evening - "so are we gonna fuck or what?" - and just as I'm saying HELL to the NO there are blue lights in the rear view.

Rodney gets out of the car and proceeds to fail the field sobriety test to the point where he's falling down (don't scruff those $500 shoes!) and he's cuffed and put in the back of the police vehicle. The officer walks over to my window (where I'd had my head in my hands not knowing whether to cry or laugh) and begins, "Ma'am, your friend here is - oh my god, Erin, is that you?" The cop was a friend of mine, Jason.

Jason says he doesn't know what I'm doing with that douchebag, but he trusts me, so he'll let Rodney off the DUI if I drive. I look Jason in the eye and I have the most twisted smile ever. I tell Jason loud enough for Rodney to hear in the open windows, "NO, he doesn't want a woman driving his car. He doesn't think women should drive at all!"

Jason takes me home, Rodney goes to jail. He calls me later asking me to pick him up - so sorry, already busy.
posted by sephira at 6:15 AM on July 10, 2009 [54 favorites]

Some highlights/lowlights from dates I've had:

This guy I had a crush on FINALLY got around to suggesting we "do something sometime" and I suggested the Staten Island Ferry, which a) is free and b) I love. We took it on a Friday night, then wandered all over NYC until dawn, talking about anything and everything. A homeless guy came along and did a really fantastic stand-up routine, and we bought him dinner at a diner. It was low-key, unplanned, and totally different from our normal lives.

A guy I'd known as a friend took me to a major city (two hours away) to see his favorite hocky team. His team lost and he was pissed, we got lost, there was a phenomenal rainstorm that led to him not seeing and therefore hitting a cement highway divider, I had to crawl under his van to check out the radiator and got coolant in my ear, and we drove two hours home terrified the van would break down any second and I would miss my curfew (which was set by my school and had some Big Punishment). This could have actually been one of those hilarious first-date stories, except we didn't mesh well throughout these difficult experiences and we didn't have much chemistry.

Good and getting better
My current boyfriend asked me out not long after we met, so it was sort of a blind date--I recognized him, but I really didn't know much about him other than his first name. He let me pick the restaurant, a Spanish place I'd really been wanting to try. We got there and I realized there was not a single vegetarian item on the menu (at the time, I had NEVER eaten meat), and our waiter only spoke Spanish. I managed to get across the problem and the waiter promised to "take care of me". He brought out a giant bowl of beans and rice which had been cooked with lard. My date ordered what he thought was a burrito and got a steak. I desperately wanted a drink, but found out my date didn't drink at all and was afraid to order one in case there was some AA reason behind this. After dinner, we went for a walk that turned into a four-hour, several-mile wander around our neighborhood while we talked about anything and everything. I finally had to go home because I was wearing heels and I was in a tremendous amount of pain (and I was too shy to invite him back to my place or go to his).

At my corner, he gave me the best first kiss I've ever had. A few days later we went out again (and I wore more comfortable shoes!) and we've basically been inseperable for the last year and change.

It was an OK date--even if things hadn't worked out between us, I wouldn't have said it was bad. What made it good was that we clicked and the snafus that came up (the food, not speaking the language, etc) weren't big deals to either of us. We established a great baseline friendship (if there hadn't been chemistry, we would have been happy to stay friends) but we also had a romantic chemistry. The date left room for improvement (one of the problems, in my opinion, of planning the Perfect First Date--where do you go from there?) and it left us wanting to see more of each other.

So I wouldn't try to plan a huge Big Deal First Date. Plan some fun, interesting thing to do that can help drive conversation. Include food. Make it clear that you're asking for a date, not to "hang out sometime" and make it clear who's paying. Leave it open-ended in a way that allows you to either extend it or get out gracefully. Leave room for improvement on a second date!
posted by peanut_mcgillicuty at 6:58 AM on July 10, 2009 [2 favorites]

My best first dates usually involved evenings that didn't go according to plan. If the other party puts up with you making lemonade out of lemons, they're worth being with. I had made reservations at a medium-quality restaurant, to be followed by coffee, to be followed by Esther's Follies. We tried to meet at a Starbucks, but a) she was half an hour late, and b) being a blind online date, we didn't recognise each other, so she waited for me inside and I waited for her outside. We still made the restaurant in time. We made it to the coffee joint, but a) we couldn't stop talking, and b) it began pouring rain, so we dropped the Esther's Follies idea and kept talking. We had to be kicked out at 1.30am.

(The relationship that followed sucked royally, but that's beside the point.)

I have all sorts of shitty date stories, because online dating encourages that sort of thing. Occasionally I was the cause, but I hope I can say I learned from it. But the all-time winning awkward date:

I: 'So, what does your dad do after having left the oil business?'
She: 'Nothing.'
I: 'Ah, taking it easy, eh?'
She: 'No, he's dead.'
posted by spamguy at 7:34 AM on July 10, 2009 [1 favorite]

Best first date:

Air Hockey. Full stop.

Worst first date:

Dancer in the Dark + clumsy makeout maneuvering which led to a hand injury. Best not to ask.

Good luck on the date, you charmer you.
posted by orville sash at 8:03 AM on July 10, 2009 [2 favorites]

One fine day, my mom's car was in the shop so I picked her up from work. While waiting for her, I spied a smokin' hot dark-haired manly type leaving her office. Who dat?, I asked. She wasn't sure but knew him by sight she said.

Months passed and she ended up meeting him at the office holiday party. She passed along my number (with my permission). Hotness and I talked on the phone several times and agreed to meet up over the holiday break.

Well. We met. And. It. Was. Not. The. Guy. I. Saw. That. Day. It was some other random dude that my mom thought was the guy I saw, who bore no resemblance whatsoever to my Dark Haired Hot Man. Silently cursing my mom, I was trapped on the date with Mr. Unrelated, whose big plan, btw, for our date was to go to the mall to exchange an astoundingly ugly sweater he had gotten for Christmas.

I dislike many things on this earth, but one of my main peevers is lack of preparation. Mr. Unrelated had no date plan whatsoever and also no receipt to exchange said fugly sweater. So my first thirty minutes with him were spent haggling with an underpaid JC Penney's store clerk over his lack of sales receipt.

The second kicker was that he had actively chosen - chosen, mind you - to wear pants without a fully functioning zipper. So he spent a good amount of time fondling his crotchal area, fiddling with the zipper. "Oh, these pants always do this," he announced. Wait. So you knew these pants would not fully cover your apparatus but opted to wear them on a date anyway? Awesome. Thanks for that.

Somewhere in the midst of all this he told me he was a musician and just doing the 9 to 5 thing while waiting for his big break. Could I have cringed deeper? I don't believe so, no.

As an added bonus, he let me pay for everything, too. (Alright, now I'm just riled, years later.)
posted by December at 8:57 AM on July 10, 2009 [4 favorites]


We went to a movie. My sister dropped me off because his driving privileges had been revoked. He "forgot" his wallet, so I bought tickets. After we got our seats, he asked me if I was hungry and wanted something to eat. Dumb as I had been to agree to go with him in the first place, I was smart enough to see this as a ploy to get me to buy him more shit. So I said, "Nope, not hungry." He pouted for most of the film.

He would only drive me part-way home for fear of being caught driving. We walked about a mile through cornfields and woods. Of course, I kept slipping so I was covered in mud and leaves. At one point, we both slipped and managed to crack heads together, which made my vision blur and my ears ring.

And I can't help but wonder if I somehow should know December, because his fly was totally unzipped the entire time.
posted by motsque at 9:12 AM on July 10, 2009

Worst: Dude from the internet. He insisted on meeting at a teahouse. That's fine, but I really loathe tea and wanted something else to drink. He ordered over me and got bubble teas for both of us and acted all pissy when I didn't drink more than a couple sips to be polite. Then we sat down and he talked about himself for a solid hour and a half with nary a single question for me. I heard all about his job. His amazing skill set. His drive, ambition, and integrity. His five-year plan for world domination climbing the corporate ladder. When I didn't gush all over his character as he was clearly expecting me to do, he walked me to my car and I sort of waved goodbye in his direction and ran away.

Not quite as bad, but still cringingly memorable: I had just moved to London and, prior to arriving, had been having a really great email conversation with a guy I'd met online through an American expat group, so we met in person at a restaurant he'd chosen. Well, I don't know quite what happened, then but somehow we just could not manage to keep a conversation going more than a couple sentences at a time, and we wound up sitting in excruciatingly uncomfortable silence most of the time. We ordered a couple sangrias, he asked if I was interested in sharing the paella, I said sure, and the waitress departed with our order. A minute later, I realized with horror that the paella had been listed as needing nearly an hour to make.

Best: We arranged to meet at a pub for drinks. (Easy out in case things turned out to suck). Well, we had our one drink each and were really hitting it off, so after a time we ordered dinner. Then dessert. Then a couple more pints. Somewhere during the evening, we'd settled into a Q&A format, each of us taking turns asking the other one a question (then having to answer it ourselves), and it was really fun and we learned a lot of hilarious and obscure facts about each other. When they finally kicked us out, he brought me back to my car and had a really nice first kiss. (Oddly, our second and third dates were terrible and things fizzled between us really quickly. Lucky for me, though, since I met my husband just a couple weeks after that.)
posted by anderjen at 1:06 PM on July 10, 2009 [1 favorite]

My best and only real/official first date was to see Tom Waits live at the Orpheum. He opened with "Singapore" and rolled out a piano and did "Martha." Crossing the street to go in, my date took my hand and beamed at me saying he was so glad we'd become a couple (the uh, weekend before) so now he knew how to act at the show, no awkwardness or confusion (we were friends first and had bought the tickets and made plans as friends only...then I got dumped by my previous guy, and well, the rest is history).
posted by ifjuly at 2:20 PM on July 10, 2009

I went on a date and told the guy how I was into art, had been an art history major, etc etc.

His response was to ask me what my favorite color was.
posted by whoaali at 5:32 PM on July 10, 2009 [6 favorites]

Best first date: we went to see a series of skits written by Shel Silverstein. We laughed at all the same parts and quoted them to each other on the car ride home. Before the play, we had breakfast-for-dinner at a diner down the street from the theater. He let me pay.
posted by coppermoss at 6:30 PM on July 10, 2009

Worst #1: Guy shows up to the date 20 minutes late, filthy, reeking of B.O. He says he's been working in the yard and forgot the time. We order lunch. Guy tells me that his father's funeral was three days prior. I can't believe that the guy wanted to go out on a date after his father had just died. I ask him to tell me about his dad, thinking maybe he'll share some good memories. The date sort of turns into a therapy session at this point as the guy proceeds to tell me about how his dad was abused as a kid... I finish my food really quickly and say goodbye.

Worst #2: Guy gets hammered (actually drinks *my* drinks too), shows me dirty pictures on his cellphone, gets all grabby with me. Even so, I made out with him at the end of the date. But there was no second date.

One of the best first dates was with another Mefi member, who showed up to the pub where we agreed to meet with a copy of The Yeti Researcher in hand. Things were all uphill from there.
posted by medeine at 1:19 PM on July 12, 2009

Excuse me as I lament the fact that I've been on so many horrible first dates I can barely register a shudder at the memory of them.

One does stand out though, because it was the first time I'd ever agreed to go on a blind date. A few weeks prior to the date, I'd interviewed with some partners at a small law firm for a low level just-out-of-college job. I did not wind up working there, but a few weeks into a new job elsewhere I received a strange call. It was an attorney from the small firm, but one whom I'd never met. He informed me that his partners told him they would fire him if he didn't ask me out on a date. I found this charming and flattering, so I agreed to go out with him. I was living in Boston at the time and he insisted on taking me to dinner in the North End. Because we hadn't even met yet I tried to negotiate drinks or coffee instead, but he wasn't having any of it. (First red flag.) He insisted that he had "connections" at the restaurant (and I was young enough that I was unable to convincingly put my foot down).

When he came to pick me up I discovered that he looked like a much less attractive version of George Costanza. I decided to focus on his personality and bright blue eyes. During dinner I keep trying to keep the conversation light. He kept giving me salacious looks while pursing his lips, and hinting that he'd like to spend time with me in my apartment alone. {shudder}

At the end of dinner the check comes. He holds the bill out in front of his face with his arm fully extended, again pursing his lips. Uncomfortable, I offer to help pay. "Oh no, I got it honey." Ick. But he STILL kept holding that damn bill in front of my face as if it were supposed to impress me. Ick. Finally, after many excruciating moments, he gets out his wallet and triumphantly throws down his Amex card. Except this is the North End, Boston. Where cash is king. The waiter arrives and reminds him of the cash only he turns to me and says, "Well in that case, it looks like I will need your help." Sigh.

Then he says, we must go get desert while we're here, we have to. I say no, I'm tired, but relent after much bullying from him (again, I was young). But he says, first I need to stop at the ATM machine to get some cash. Great idea, I reply, now that I don't have any cash left. He lets me go first, and I get out some money. He suddenly says, "Damn, I left my ATM card at home!" Good lord. So yeah, I ended up having to pay for dinner and dessert. And then he had the nerve to try to get in my pants. (Don't worry, I wasn't that naive.)

Needless to say, I ignored all his phone calls (and it took many years before I would agree to go on another blind date).
posted by ohyouknow at 3:09 PM on July 16, 2009 [1 favorite]

Response by poster: Okay, folks, tonight's the night.

Thank you so much for your stories and your advice - they've given me a lot of good ideas and made me rethink some potentially disastrous notions. I think this thread went really well - it's certainly a blast to read!
posted by EatTheWeek at 9:56 AM on July 20, 2009

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