Fifty First Dates. (OK, more like three.)

July 28, 2010 1:38 PM

What should I say on a first date?

I've had a recent (and somewhat unbelievable) increase in the number of replies to my online dating emails. I guess this means I'll be going on a lot of first dates in the near future, with people that I don't yet know much about. Any ideas about what I should talk about? Interesting questions I could ask?

If it matters, I'm a man in my early thirties, and I'm interested in women.

Before you ask: Yes, I'll do my best to Act Natural, Be Myself, Be Interested in Her, and all that. I won't go in with a script. I'll try not to overthink it. I'm just looking for some ideas.

posted by sesquipedalian to Human Relations (39 answers total)

What do you do for a living? Why do you do that?
posted by amethysts at 1:40 PM on July 28, 2010

What are you passionate about?
posted by inturnaround at 1:41 PM on July 28, 2010

What are you the most proud of about yourself? What would your Mom and/or Dad be the most proud of you for? (This brought out some very interesting answers on both sides on my first date with my SO.)
posted by MexicanYenta at 1:42 PM on July 28, 2010

I think it depends on what you value. I like talking about travel and interesting travel experiences. Sometimes I'll get "I would never do/try/eat that..." responses, or outrage that I've eaten dog meat or gone to a gay club in China or whatever. When that happens, I know she's not for me. It's a nice way to cull the herd.
posted by smorange at 1:44 PM on July 28, 2010

Ask her about herself, and listen to what she says instead of thinking about what you will say next. Respond when appropriate.
posted by Kafkaesque at 1:45 PM on July 28, 2010 [1 favorite]

Just get her talking about things that make her happy. Her childhood. Her passions. Her favorite brand of cereal. Whatever. Do NOT talk about cool, crazy things you've done or what you're proud of. Work is pretty boring too. You want to hit her emotional core in a sweet way, aim for that. Puppies. Causes. Things like that. JMO
posted by Nixy at 1:46 PM on July 28, 2010 [3 favorites]

I like when people tell me about their favorite books.

I dislike long stories about travel and adventures that are meant to make the teller seem interesting.

I dislike talking about careers and backstories, but the caveat here is that I also HATE DATES, and that most people on a date do expect this kind of get-to-know-you conversation at some point.

I dislike open-ended questions like "what are you passionate about?" because it's difficult for me to answer that with a straight face.

But most women on online dating sites like dates, so, as they say in acronym form, your mileage may vary.
posted by millipede at 1:47 PM on July 28, 2010 [2 favorites]

I'd focus on manners. Ask more questions than you answer. Stay away from obnoxious topics/religion/politics.
posted by cjorgensen at 1:48 PM on July 28, 2010

It also depends on what kind of date. I think I like dates that involve doing things more; it's much easier to judge by actions than by words. In that case, what you should talk about are your natural observations of the world around you, and you should ask about (and really listen) to hers. This might help avoid the job-interview feeling that first dates can be plagued with.
posted by nat at 1:50 PM on July 28, 2010

If you could sing like anyone, who would you want to sing like?
posted by Joe Beese at 1:55 PM on July 28, 2010 [1 favorite]

Yeah, figure out what it is you are passionate about and go with that. You will have a natural enthusiasm on the topic, and people generally respond positively to that kind of internal happiness. Just try not to make it the thing you talk exclusively about.

Ideally, see what she reacts to when you first start talking and then focus on that for a while.

You: "Lately I've been really getting into photography. Mostly wildlife stuff, I really enjoy being outdoors and it give me a good excuse to sit out in the sun waiting for a bird or critter to wander by..."

Her: "Oh, I love birds, that must be interesting..."

You: "Yeah, I really enjoy it. So, do you keep birds, or are you just a fan of the species in general?.."

And then you let it be about her for a while. Don't monopolize the conversation, and don't be too passive. Listen to what she likes and try to tie that back to the stuff you enjoy.

And thus, bridges are built.
posted by quin at 1:56 PM on July 28, 2010 [1 favorite]

There are a few topics that are evergreen: What you do for a living; why; how. What you study/studied in school. Where you grew up. These are safe. On the other hand, they can also be pretty boring. If you're doing online dating, you have access to your date's profile - you hopefully have a clue about what you have in common. I'd much rather talk about my favorite books, or movies, than have to describe my job yet again. Also, knowing what I do for a living doesn't tell you very much about me that you couldn't figure out very quickly from knowing me at all; you might, however, have some insight into me if you learn that I love The House of Yes and Buckaroo Banzai and Catch-22, and despise Hemingway.
posted by Tomorrowful at 1:58 PM on July 28, 2010 [1 favorite]

Don't ask too many questions. You gotta do some talking, too.
posted by RajahKing at 2:00 PM on July 28, 2010

Hopefully the conversation will flow naturally and you won't really have to think about what to talk about. You only really need to have specific questions or topics in mind to avoid awkward silences and that sort of thing. So just have some of those in mind and gauge her reactions and use what you know about her to figure out what she wants to talk about. If she lights up and talks a lot about a subject keep going in that direction, if her eyes glaze over or she acts less than enthusiastic then switch to something else. Those kinds of non-verbal cues actually make it easier to have a good conversation in person than online in my opinion.
posted by burnmp3s at 2:01 PM on July 28, 2010 [1 favorite]

I find the usual questions boring. I like to ask questions that generate discussion and are still organic to the conversation I'm having. If I know someone's a music fan and we're talking about music, I might ask who they think is a more influential artist, David Bowie or the Velvet Underground. (You can ask her about favorite restaurants of a particular type or in the neighborhood, favorite summer movie, etc.) If I know someone has a PhD in economics, I might ask some lingering question I had about something I read in the paper having to do with that issue. If the questions are too "big" and unrelated to your conversation, it'll seem like an interview.

I know I'm having a good time if I forget to even ask the usual questions.
posted by *s at 2:10 PM on July 28, 2010

2nding hating date situations, since they're practically like job interviews.
Try to diffuse the situation, if you can. I'm not saying that you should be a ham, but do be aware that she's probably feeling the same stress that you are. Try to be comfortable, try to make her comfortable, then see where it goes from there. That should give you a good idea of how compatible you ultimately are.
posted by Gilbert at 2:16 PM on July 28, 2010

Three words:

Rock! Paper! Scissors!
posted by storybored at 2:17 PM on July 28, 2010 [3 favorites]

I think it's fun to ask people about their guitly pleasures, or things they like that they are a bit embarrassed about. Do so gently and with a light tone, and never react with horror! The person will often talk about eating devil dogs for breakfast or going to see Bel Biv Devoe and you'll get to see a bit of their character and humor.
posted by xo at 2:18 PM on July 28, 2010 [1 favorite]

Try to talk about less-obvious aspects of the standard questions. While "what you do for a living" isn't the most exciting topic, it's just possible your date will ask you a fairly bland question, so it's nice to be able to turn a bland question into something you both can talk about, beyond just exchanging job titles. But instead of getting into the long answer of what your career is all about and your passions for whatever it is you do, and hoping that will give her something to relate to, tell a (short!) story that's tangentially related. "I've had this job for almost 2 years, and it's working out pretty well. It's the first time I've worked in a classic "office environment" with cubes and all that, so it was kind of an adjustment for me, like when ..." And who knows - in addition to anything related to your actual choice of career, you might end up talking about her workplace, making friends at work, embarassing overheard phone conversations, whether it's better to have a mediocre cafeteria or none at all, how she's managed to avoid ever working in a cube, how important a non-traditional office is to her way of thinking....
Basically, feel free to answer a "boring" question briefly and launch on a tangent, because the more ground the conversation covers, the more chances you'll have to hit a good connection or funny moment that will make the date really click.
posted by aimedwander at 2:25 PM on July 28, 2010

Ugh. Do not ask someone what they're passionate about. That's a total job interview question and would make me very uncomfortable. Ask if she's seen any good movies lately. That's an innocuous question that could lead to some other topics. Ask maybe about something interesting she's wearing (Cool glasses, where did you get those?). Not only is it nice to compliment someone, assuming you actually do like the glasses, but it allows you to talk about activities and maybe will lead to a discussion about a neighborhood you both like. The goal of asking a question isn't necessarily to get the answer, it's also to keep things moving. By asking questions that lead to other sources of conversation, you'll be one step ahead towards the next question.
posted by otherwordlyglow at 2:34 PM on July 28, 2010 [11 favorites]

What's the best thing you've eaten recently?

Leads to all manner of interesting side-notes, related stories, and general chat while also avoiding all of the usual job/life stereotype questions. It also tends to be a somewhat unexpected/atypical question (in my experience, anyway), which is a bonus. However, this only works if you care, or strongly do not care, about food. If you're actually entirely neutral on the topic, it's a dead-end trap. If she is also entirely neutral about food, it will fail.

...but odds are it'll lead to interesting discussion and you'll learn important things.
posted by aramaic at 2:39 PM on July 28, 2010

Observe. Ask. Listen. React.

Observe things about the person, the day, the situation.
Ask questions or say things relevant to what you've observed.
Listen to what they say. Really listen. Don't just wait your turn.
React to what they've said, specifically, and explore it further.
posted by seanmpuckett at 2:58 PM on July 28, 2010 [1 favorite]

When I'm around a stranger I just act like I've known them forever.

I just start talking about some funny thing that I heard or that happened to me - just start blabbing in a friendly, chatty way to begin to establish a rapport between the two of you in a natural way - mainly to get past the awkwardness of the situation.

Having a drink together helps a lot!

Hopefully, your date will connect with what you are saying or in your friendly manner and chime in with something similar that she heard or that happened to her and you can start finding mutual areas of interest/humor.

Humor is huge!
posted by Tullyogallaghan at 3:22 PM on July 28, 2010 [6 favorites]

I find that sometimes, acting like YOURSELF around total strangers, especially in a one on one situation, is actually the "natural" way to go. You just have to let it flow.

I think of it this way: Everyone else I know has some preconceived notions about the way I will act. They have pegged me; they have their mental image of who I am and my actions should conform to that image in their mind. I think about them having those preconceived notions and it affects how I act and what I say. However, a new person is a fresh slate to whom I can say anything that I want and with whom I can act how I truly feel.

This 1) is fun and 2) increases the likelihood you will find someone that you really should be with, as when you act like yourself you attract the right people.

Say the things you truly mean, and ask questions with answers you truly care about, and the right people will respond in the right way.
posted by 3FLryan at 3:37 PM on July 28, 2010

Be more interested in finding out about your date than in talking about yourself.
People love to talk about themselves - listen to your dates life story.
posted by Flood at 3:48 PM on July 28, 2010

Be polite to the waiter.
posted by BusyBusyBusy at 3:58 PM on July 28, 2010 [4 favorites]

Can I offer a suggestion that helps shape conversations in a positive way?

I thought so.

Please don't go have coffee. It's just too much like a job interview. Pick a date that is an activity, but that is not expensive. Set these activities up so that you're in a group, but not a group of your (or her) friends.
Canoeing
A picnic
Birdwatching (seriously, don't offer to take her into the woods alone)

Um, other stuff suggested by her profile. She likes to cook? See if she'll take a cooking class with you.

Please note that some women really, honestly prefer the coffee date. So if she suggests coffee, roll with it. But if a guy is suggesting a date, I really prefer that he demonstrate an idea of what I like to do.

Then we can talk about cooking memories, favorite dishes, food allergy experiences, holiday meals, etc.

Or bird watching memories, favorite sighting, best times/places to watch.

Or canoeing experiences...you get the idea!

I feel like you learn a lot about people from these conversations, because they aren't rehearsable and they don't feel forced. 'What do you do for work?' is so rehearsable, and such a land mine in this economy.
posted by bilabial at 4:01 PM on July 28, 2010

Improvise. That is, acknowledge and accept what she's said and then riff on it. Put a twist on the information she's given you.
posted by Araucaria at 4:07 PM on July 28, 2010 [1 favorite]

How was your day?
posted by jadepearl at 4:40 PM on July 28, 2010 [1 favorite]

Tangential anecdote: A piece of folklore in my family relates how a farm boy (this is back on an island in the Netherlands) was asked by his girlfriend's mother to come over for a cup of tea, a set part of the courtship ritual in those days (probably the 1920s). He asked his mother what he should talk about. Mom says, "Well, you just talk about whatever comes up. For example, when she pours the tea, you say, 'My mother's got a teapot just like that', and the conversation will just flow." So, boy goes over for tea, says "My mother's got a teapot just like that," and girlfriend's mom says, "Oh, really?" End of conversation.

So the point is, as has been said here variously, you need to listen, you need to react, you need to improvise, you need to ask questions and respond to the answers, you need to find connections.
posted by beagle at 4:55 PM on July 28, 2010

So I love to talk. I am just naturally gregarious and so are my parents and pretty much all my friends so I spend a lot of time making a concerted effort to be quiet (at work, at school) or vying for talk-time against said friends and parents.

On my first date with the man who is now my husband, he did something no one had ever done before: he asked about me, and asked about me, and showed he was listening and then asked about me more the whole time assuring me everyone 5 minutes or so that he was really enjoying listening to me talk and that he wanted to hear more.

I left feeling like the most fascinating person in the world! I felt like he was SO in to me that he couldn't get enough of my stories and I told all of my favorites. That date is a memory we revisit often and fondly. Plus, on our next date I felt so LIKED by him that I was anxious to find reasons to like him, I was actively looking for reasons to like him because I liked how he made me feel. We spent the next date with him being the one talking the most.

Though it won't work on every date, I suspect many other talkers would feel the same way I did after this kind of treatment. Just a thought.
posted by Saminal at 5:11 PM on July 28, 2010 [1 favorite]

(Further to Gilbert's good advice) The biggest threat to a first date is the pressure and self-awareness both parties feel knowing that it's a first date. "Date? My gosh, that should lead somewhere shouldn't it? But what if it doesn't? Maybe it's her, but it could be me...is it me? God, I feel so phony. I wonder if she's picking up on it...." (Ad nauseum, perhaps literally).

Do whatever you can to minimize the pressure on yourselves to behave like you're On A Date. If applicable, that includes totally obliviating the idea/hope/expectation that you're going to get some at the end of the night.

I also hate to say it, but The Game by Neil Strauss, as well as his and other "PUA" systems, have some good insights into why dating is so stressful and why "pickup" is so effective: it's because pickup artists try to avoid coming across as putting the moves on women. And while "Game" is a little too analytical and reliant on psychological manipulation as to be something admirable, the general approach to breaking down barriers and de-stressing a boy-girl meeting seems to have a good deal of common sense and value.
posted by holterbarbour at 5:22 PM on July 28, 2010

I know this makes me sound boring, but wacky/"interesting" questions straight out of one's pocket totally turn me off of a social situation. If someone asked me something like "Which piece of furniture would you be, and why???!!!111", I'd feel as though I was playing a board game, not talking with a real person. If it comes up somehow in the conversation, go for it, but strange prepared questions, in my opinion, can be really awkward and showy. I swear I'm not a totally imaginationless piece of stone (I do improv, and do like to talk about weird things), but there's a difference between being WACKY!! and being genuinely interesting. YMMV.
posted by threeants at 5:26 PM on July 28, 2010 [3 favorites]

My advice is to keep it lighthearted and chatty, not like a job interview or therapy session. No "What are you passionate about?" or "What are you most proud of?" (no offense to people who suggested these, but those sort of questions would make me feel nervous and awkward)

Things like "where did you grow up? or do you have any siblings?" are easy, low pressure questions. Also, it's okay to talk about your interests as a starting point- let's say you love movies, ask if she's seen anything good lately and tell her about a movie you saw.

I also like the advice to act like you already know the person- no forced interview questions, but a simple "how was your day? is goof, more conversation about the surroundings (hey, i heard the dumplings here are fantastic. should we try some?"), or something that happened to you that day "I saw a lady with a pet rat on the train on my way here", or what have you.
If you're both drinkers, a drink or two can ease the tension, and yeah, obviously try to go with the flow and not rely on some sort of script.
posted by emd3737 at 7:05 PM on July 28, 2010

One of the easiest conversations I had from an online date started, "If I could be anything else in the world, I'd be a novelist. What would you be?" I said a Broadway singer. Then it was easy following with questions like why he'd like to be a novelist, what he'd write, and so on. If she doesn't pick up on the lead, you can ask her questions about her secret impossible dreams.
posted by motsque at 3:26 AM on July 29, 2010

Conversation is almost like an art. So few people know how to do it correctly and when you find yourself in a great one it's like nothing else.

Scott Adams (yes, of Dilbert) has been writing about it recently. He has a good approach:

"...as a general rule, conversations about how people have or will interact are interesting, and conversations about objects are dull. So steer toward topics that involve human perceptions and feelings, and away from objects and things."

I think that's pretty spot-on. On a first-date I'm always looking for a great conversation. It helps having a wide variety of interests and opinions as well as an open mind. If you can talk a bit about anything that interests her, you'll have it made. And even if you know nothing, so long as you know how to ask the right questions you can sound interested and engaged.
posted by fso at 8:17 AM on July 29, 2010 [2 favorites]

When you connect with someone, conversation just flows naturally. But to get it started, I think jadepearl was spot on with the "How was your day?" question. From there, just listen and pick out things to ask more about as they come. If there's a lull, ask about something from her profile, but phrase it to eliminate the fact that you're talking about the profile (for example, "So, you're into waterskiing, right? Where are the best places for that?" NOT "You had a picture on your profile of you waterskiing and you mentioned it in your self-summary."). The only caveat: make sure you are asking about her profile and not someone else's. I've been on dates where someone asked me about something that was not on my profile, and it was rather awkward when he realized he'd mixed me up with another girl.
posted by Fuego at 1:27 PM on July 29, 2010 [1 favorite]

Response by poster: Wow! What an amazing set of responses. Best answers for all of you.

Anyway, First Date #1 is tonight. Wish me luck!
posted by sesquipedalian at 4:07 AM on July 30, 2010

Ask questions with open-ended answers: "Oh, you just moved here? Why'd you choose [this place]?" is much better than "How long have you lived here?"

Inquire about things that you don't know about: "Wait, what did you say about [such-and-such]? I don't even know what that is. Tell me more..." and "You're into [something]? Is [this place] known for that?" show that you're inquisitive and interested in your date.

Also, I think having coffee/tea/a drink on a first date is perfect: it's simple, cheap, and time-limited. There's nothing worse than being 20 minutes into a failing date and knowing there's still another three hours of [whatever activity] until it can be over. And if things are going well after a cup, you can always extend with a walk, etc. or make additional plans for the near future.
posted by fracas at 8:47 AM on July 30, 2010