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June 13, 2011 7:20 PM   Subscribe

What can I do to make first dates more fun and interesting, and less like a job interview?

You know how when you meet someone at a party or through a mutual friend, you sometimes just hit it off? There's good conversation and playful flirtation, and then when you go on the first official date things are just sort of cool and relaxed? How do I replicate that situation on a blind okcupid date?

I went on several first dates through okcupid last year, took a break, and now I'm back and have got one coming up in the next week. Those dates last year were all fine, but I felt like they were lacking in...something. Conversation flowed, but it was all very interviewish. I'd ask a question, and she'd answer. Then she'd take something she said and ask me a question about it. Then we'd go back and forth. It wasn't very fun, and I felt like I was doing something wrong.

So how can I make the first date more like, say, the fifth date? Are there questions I can ask, or other tips which might help? Or is this just an inherent feature of blind dates arranged on the internet?

(late-20s straight dude in NYC, if that matters)
posted by soonertbone to Human Relations (31 answers total) 63 users marked this as a favorite
Find out what she does for fun and do that on the first date. If she likes sailing, go sailing with her. She'll feel confident and in her element and you'll get over that 'what do we talk about' hiatus over an awkward dinner. Remember that any girl is going to be a bit careful on a first date and want to find out more information when first meeting someone they've met over the internet, particularly as people do tend to overplay their attractiveness and accomplishments online. If by 'getting to the fifth date on the first date' you mean how do you get her into bed at the end of the night then that's something else entirely.
posted by joannemullen at 7:35 PM on June 13, 2011 [1 favorite]

Response by poster: Uh, just to clarify: the fifth date comment was asking about how to attain the comfortableness and ease of conversation that you often have with someone after a series of dates, after the awkwardness of the first couple dates has worn off.

NOT looking for advice on getting anybody into bed.
posted by soonertbone at 7:46 PM on June 13, 2011 [1 favorite]

Don't do things that necessitate constant conversation (like going out to dinner). Instead, try doing something more "interactive:" go to an art gallery or museum; take her to a concert; basically, put yourself in a situation where you both have the opportunity to engage in something other than each other.

This will relieve the stress that comes from feeling like it's your job to keep up the conversation. Plus, if it turns out you two have nothing in common, you already have something (whatever the activity is that you are doing) built in that you can discuss.
posted by lobbyist at 7:50 PM on June 13, 2011 [6 favorites]

Go do something playful and interactive like a science museum.
posted by J. Wilson at 7:57 PM on June 13, 2011 [1 favorite]

Don't just get coffee or drinks--that puts all the pressure on you guys to entertain each other. Do something that entertains you guys together. Cook together, go for a walk, go to an event or concert.

Ease and comfort does tend to come with time, though.
posted by mollymayhem at 7:59 PM on June 13, 2011 [2 favorites]

Take her geocaching. I've done it a few times with women, and it's always a hit. I think the wandering around makes you less inhibited, plus you have a problem to solve together, and there's a sense of adventure and intrigue.
posted by alphanerd at 8:01 PM on June 13, 2011 [2 favorites]

God, I hate that! So much so that I cringe when I hear others doing it at a restaurant (nice ones, too!) or a coffee shop. "Oh jeez, they're on a blind date." There's just no way in hell to pull a relationship out of an interview, not even a casual sex one.

Anecdatally, I have found in several years of online dating that dates that go like interviews mean that the person is BORING. I am beginning to learn that it's not me (though they are probably looking for a guy who can control the conversation...too traditional for me), but that it's an indication to just cut the date short. It sounds cruel, and this is just another point on the "numbers game" aspect of dating that I hate. HATE. I'd love it if the easy email translated into easy dates, but I've realized that it's an inverse relationship.

Conversely, those women who I've been able to banter and come up with a cool date idea are most likely to flake (speaking from SF here). Sad but true, so I think I'm gonna keep it to the middle: always try to do something that provides a distraction: galleries, sports, the symphony, hiking...whatever.
posted by rhizome at 8:03 PM on June 13, 2011 [5 favorites]

Go to a class together, like cooking, or rock climbing, or a dance class, of a wine tasting class, or something. something where you are both focusing on learning x, rather than on solely each other. no one has the edge over the other, because you're both learning. good times.....
posted by anitanita at 8:23 PM on June 13, 2011 [2 favorites]

Best answer: I've had a lot of experience with online dating, and I'm going to go against the grain here ad suggest that you NOT do something like sailing, or geocaching, or anything that will put the first "date" over 2 hours. I tend to think of the first date as just a meeting, and treat it very differently than if it were a date with someone I already knew. For example, I went on one "OKC meeting" last week and we just went and got some ice cream and went for a walk. I take it as an opportunity to find out if you want to actually go on a real date with the person. Yes, it can feel interviewish (if you take that approach), but focus more on having a nice conversation in the moment, find out what she likes to do, not what she hopes to get out of a relationship, and then at the end of the meeting you and she can decide if you'd like to meet again.

My OKC date/meeting last week went well, and now we have a real date set up for this Friday for dinner and a museum. Had we planned that kind of date for the first meeting, and it turned out we didn't click, that would have been torturesome.
posted by Sal and Richard at 8:29 PM on June 13, 2011 [24 favorites]

There are many great ideas here—for a first date with someone you already know. They don't seem so great to me for someone you've never met before. There's way too much time commitment for someone who could turn out to be a total and complete mismatch.

I agree with Sal and Richard—don't think of the first meeting as a "date"—think of it as a meeting that you'll use to decide whether you want to go on a date or not. It's just a chance to meet someone new and chat with them for a little. You like talking to new people, right?

Also, you don't say what you're doing on these "dates," but I'd meet for drinks rather than coffee or lunch.
posted by grouse at 8:33 PM on June 13, 2011

Since you're in New York, I'll recommend How About We. The whole point of the site is to get people out and doing something, so you can just propose an activity and see who responds to it -- there are usually a range between dinner somewhere cool, or an all day bike ride, but I think most people want something in a low ish key even when it's on a novel dating site. I've met some really nice people on there, but no keepers yet it seems. Give it a whirl though, especially in summer I've been posting a bunch of dates just to have people to do some fun city stuff with.
posted by sweetkid at 8:37 PM on June 13, 2011 [1 favorite]

Also agree with Sal and Richard and grouse that it shouldn't be something too involved or expensive. I think 1 hr is just about right for a blind date.

Cocktails are great if you both drink (social lubricant and easy to cut short if it's not going well). Maybe combining coffee/tea with a walk? If you know of a place with old-school arcade games like skeeball and air hockey, that could be fun.
posted by smirkette at 8:46 PM on June 13, 2011

Yes, like most people have said: choose an activity rather than dinner/drinks.

As a mid-twenties single female, my favorite dates are always sporting events.
posted by brynna at 10:16 PM on June 13, 2011 [3 favorites]

I LOVE pub trivia as a first date.
posted by superlibby at 10:39 PM on June 13, 2011 [2 favorites]

You definitely need to go and do something together. Of course, you also need to be able to pick the right kind of thing to do (based on what you both like) but it is always hands down better than getting coffee/having dinner/having drinks. It's really the best way to not only converse with someone, but also to see how they are more fully as a person (i.e. get to know someone - which is exactly what you want). The biggest problem is when you go for dinner/drinks/coffee is that for most of the time the attention is on the two of you and it has to become a bit like an interview because there's simply no other real stimulation/interaction. By doing other things, you take the pressure off both of you AND have external things to interact with/ask the other person about so conversation becomes better as well.
posted by mleigh at 11:19 PM on June 13, 2011

Jesus christ, GO BOWLING.
posted by auto-correct at 12:14 AM on June 14, 2011 [9 favorites]

If you're into games or crossword puzzles (and she is, too), that can be a nice way to make a coffee date feel more relaxed. If the conversation flows well, you'll find yourselves neglecting the cribbage board (or whatever), but if things are feeling a bit awkward, it gives you something more natural to do.
posted by cider at 3:47 AM on June 14, 2011

Agree with the above. I'm a female and I'm on okcupid. I like my first date to be coffee or drinks - something that isn't horrifying long if for any reason I'm uncomfortable or we just aren't clicking. I've turned down some fantastic first date ideas because I didn't want to be locked in to spending that much time in an enclosed space with someone I'd never met before.

I liked the idea of games or crosswords, but I personally don't mind the interview date so much. It *is* an interview - I want to get a better idea of who you are and what you're about - and I assume you do too. When the interview slips into something more is when after the initial awkward chit-chat we linger at the bar telling jokes and weird stories. I love that.

One possible solution here is to just get through the "interview date" and then have a backup if things seem to be going well. After the coffee's downed or the drinks are empty, you could suggest walking to a nearby park, exhibit, live music performance, chess tournament, art class, etc.
posted by bunderful at 4:20 AM on June 14, 2011 [4 favorites]

I just came across two variations on a novel concept (to me anyway). Book speed dating! One version was actual speed dating hosted by a library (meh). But the other was speed booking.....if you & your new date are bookish, you each bring three books that you love to tell people about. Set a timer and you each get five minutes to talk fast about how super or horrible the book was. You'll learn a lot about another person through taste in books, there's ready made conversation, and after thirty whole minutes of talking, you'll know if you want to get some dinner or bail.
posted by motsque at 5:55 AM on June 14, 2011 [1 favorite]

Wow, I'm surprised no one has hit on the obvious. A conversation is a two-way street and if it's "interview-like", with you asking all the questions and she answering them, it's because YOU are driving the conversation and YOU are turning it into an interview.

Do you offer something about yourself? Do you pick up on something she said and relate it to stuff you like, you do, you think about? In short, do you pick up from her answer and give back a conversational reply? She can't converse with you if you don't converse with her.
posted by Sublimity at 6:03 AM on June 14, 2011 [3 favorites]

Mini golf. It is close to impossible not to loosen up and enjoy yourself while playing mini golf; conversely it offers the bonus of revealing if they are the type of person who is ultra-competitive or gets really pissed over stupid shit like losing at mini golf.
posted by 8dot3 at 6:10 AM on June 14, 2011 [8 favorites]

Taking a long walk somewhere public (so she knows you aren't going to kill her) is, I've found, always superior as a first date. 100% of the time. I find if they aren't up for taking a long walk they may suck anyway. Also...for some reason it seems really imaginative to women. I get complimented on the idea.

Bowling, btw, is tough, because you are standing and she is sitting, and then vice versa. Not much time to talk. At least, that's been my experience.
posted by sully75 at 6:22 AM on June 14, 2011 [2 favorites]

I like the coffee/drinks hour-or-two blind dates. Getting past the awkward is the fun of it. I would recoil in horror at a "lets do something" first date. The doing stuff dates can be successful, but it tends to lead to those "relationships" where after a month you suddenly realize you are with an asshole.

I also like them because they ARE kind of boring, dull and auto-pilot-like. You know you've met someone special when going through the motions of a culturally required interaction becomes fun.

(And yes, the advice to have a couple of ideas in your back pocket for extending the date aren't a bad idea. Drink your coffee, and THEN go walking/bowling/drinking/etc if the mood is right.)

So much so that I cringe when I hear others doing it at a restaurant (nice ones, too!) or a coffee shop. "Oh jeez, they're on a blind date."

Spotting those is one of my favorite pastimes, outside of toupee spotting. There is also "creepy job interview", "awkward hand holding across the table reconnecting with old lover", "mlm sales pitch" and "religions conversion attempt".
posted by gjc at 6:36 AM on June 14, 2011 [1 favorite]

Best answer: I met my wife on OkCupid. I met a lot of people who weren't my wife on OkCupid too.

A bad date will feel like an interview. There may not be something wrong with the person, but you don't have chemistry with them. If you do have chemistry with the person, you'll have a good time and it won't feel like an interview.
posted by valadil at 8:51 AM on June 14, 2011 [6 favorites]

I nth "do something that will entertain you both", but don't schedule a specific event just because someone else (like, MeFi people) told you would be fun - do something that caters to both your interests. If some chatting reveals that you're both athletic and not afraid of heights, maybe rock climbing would be a good idea. If you both like a particular sport, go watch a game. If you both like traipsing around looking for something, go geocaching. There is no point dragging a city-bred height-phobic shopaholic on a cliff-scaling expedition, you know? Do something that you both enjoy, preferably as determined by previous okcupid conversations.
posted by Xany at 10:13 AM on June 14, 2011

One of my favorite first dates just so happened to start at a restaurant on a street where there was a fair/festival happening. It was really nice to have the little set-timeframe "meet and chat" part where we see if we clicked in-person, and then have a convenient, low-key option to hang out for a while longer, casually roaming around the street fair.
posted by lizbunny at 11:57 AM on June 14, 2011 [1 favorite]

I once overheard a guy telling his group of friends about a game he has played on a couple of first dates that turned out to be really fun for him. The dates were at restaurants, and the goal of the game was to have the server either bring one cheque or separate cheques at the end of the meal, without asking the daters which they prefer.
So, the guy's goal was to have the server bring separate cheques, whereas the girl's goal was to have the server bring one cheque. This resulted in the girl having to act very flirty and relationship-y with the guy every time the waitress was around, and with the guy having to act aloof and disinterested. Of course you could switch up the roles/genders/goals, but it seemed like a fun way to add some spice to a first date.
posted by whalebreath at 4:14 PM on June 14, 2011 [3 favorites]

I came in here to say basically exactly what Sal and Richard said: yes, experience-type dates are the best way to keep the date from feeling like a job interview, but you do not want to commit to some four-hour extravaganza of fun and discover ten minutes in that you're with a total nutjob or The Most Annoying Person in the World. This is why the coffee/cocktail date is popular: it's easy to bolt early if it's not going well (and easy to linger if it is). I also agree that the people you're feeling like you're interviewing probably wouldn't be tons of fun on a more fun date either - if you're going to enjoy being with someone, the coffee will probably be just as fun as any of the suggestions here. And I think the question-and-answer part is kind of unavoidable, because otherwise you just won't know anything about each other at the end of the date.

Having said all of that, my recommendation is to meet for coffee and bring cards or a board game. Still a variable time commitment, still lets you talk a bunch, but takes some of the conversational pressure off and lets you each see who you are when you're not just talking about where you grew up and what you do for a living. (Of course, I like games - ymmv if you're not into that.)
posted by solipsism at 6:42 PM on June 14, 2011

If you go for an experience date, obviously don't commit to an all-day activity. But if it's something you both enjoy and would independently want to do, this idea that you're losing out on the ability to bolt after a cup of coffee or pint of beer strikes me as misplaced. Even if there are no romantic sparks, if you're doing something you both want to do, you really ought to be able to enjoy the activity for an hour or two.

(I don't think this is necessary. As others have noted, even on a cocktail meet and greet date, the job interview feeling fades if you click.)
posted by J. Wilson at 5:03 AM on June 15, 2011

You know how when you meet someone at a party or through a mutual friend, you sometimes just hit it off? There's good conversation and playful flirtation, and then when you go on the first official date things are just sort of cool and relaxed? How do I replicate that situation on a blind okcupid date?

Have a phone-call date first, a few days ahead of meeting in-person. You can have your good conversation and playful flirtation over the phone, from the comfort of your own homes. And when you finally get that first meeting things can be more relaxed because you feel like you've already gotten to know that person a bit.

There have been only a few guys who did this with me, so it's a little unusual - most people IM instead. In a few cases where the guy pushed hard for it right away, there was the feeling of "let's have a phone conversation first so I can figure out if the meeting will be a total waste of time, without me having to spend all that effort and money" ... don't be that guy.

Three of the guys I actually ended up dating for a while were the ones who came across with "I think you're really awesome, and I can't wait to meet you in person on (Friday). I've been thoroughly enjoying our conversations over IM and email, and I keep thinking I'd really like to hear your voice and your laugh - I feel like I'm missing out on that when we chat on the computer. So, would you mind if I gave you a call tonight?"

I don't advocate pushing for a videochat with someone for a first live conversation though. There are several reasons, but the main one is that it implies that you want to make sure they really are the person in their pictures. I've heard some very weird stories relating to this false advertising, but that won't change the fact that you're giving off the vibe of being shallow, distrustful and aggressive.
posted by lizbunny at 10:48 AM on June 15, 2011

I love museums for a first date. It allows you to talk, or not; to walk, or sit; and provides plenty of conversation starters.

Also, I think it gives a look into the other person's aesthetics. They don't have to match mine; but I can see if they're radically different (i.e., not open to ideas outside their comfort zone).
posted by IAmBroom at 7:12 AM on June 18, 2011 [1 favorite]

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