Dating 101: Conversation

October 29, 2005 3:07 PM

How do I get someone to open up on a first date?

I have a date with a girl I met at a party tonight. She's notoriously shy, quiet around strangers and her friends say she has trouble opening up to new people. I have had a couple of conversations with her and she finds ways to turn open ended questions into closed answers, so the standard procedures have failed, so far. I know that she's interested (that's not the issue), but how can I make sure the conversation flows well on a first date?

I'm not a natural conversationalist (I prefer to listen) and so it may be simpler than I think, but any hints are appreciated.

posted by dflemingdotorg to human relations (29 comments total)

Ply her with alchohol!
posted by delmoi at 3:11 PM on October 29, 2005

Make her issue your issue and talk to her about it. Say to her something like "You know I'm kind of shy and have a problem with opening up to new people. I wish I could change that." The negative is that it's manipulative.
posted by Carbolic at 3:14 PM on October 29, 2005

Or ply her with alcohol.
posted by Carbolic at 3:15 PM on October 29, 2005

Engage in activities that don't require conversation. Once she's comfortable, she'll open up. A good example is something active like a game of cards, where you have to talk to explain rules and play the game. If attraction isn't the issue, the little conversation you do have will be natural instead of forced.

It's also OK to enjoy silences, even with someone you don't know too well. As long as you're not uncomfortable when there's not conversation, she'll probably be OK, too.
posted by Happydaz at 3:30 PM on October 29, 2005

Happydaz is right...it sounds like she doesn't like conversation just for the sake of conversation. That being the case, if you want her to feel at ease around you, don't put a lot of effort into getting her to talk. She'll probably be relieved.
posted by bingo at 3:36 PM on October 29, 2005

Hi DFleming, what time are you picking me up? Your date sure sounds like me. I really hope your plans involve some kind of activity, so that the conversation can be about whatever you're doing (the movie, the museum exhibit, etc). Otherwise, small talk is painfully hard. (The good news: once she gets to know you and feels comfortable with you, she'll probably chat more easily.) But until then, you're probably best avoiding the usual topics of small talk, and try some meatier but impersonal subjects: books, history, the arts. etc. I'll bet she's a geek with some pretty varied interests but just doesn't like to babble about them because she's found that most people's eyes glaze over when she talks about the esoteric stuff she likes. But if you show genuine interest, she'll be delighted to discuss antiphonal harmony, or Byzantine mosaics, or Chinese bird-and-flower paintings, etc. Just don't try to get her to talk about herself until she's ready.
posted by Quietgal at 4:07 PM on October 29, 2005

Ply her with alchohol!

Might not work: I become even more introverted while under the influence of alcohol.
posted by koenie at 4:26 PM on October 29, 2005

I've dated a lot, and here are my tried and true first date tips:

1) Plan a bunch of talking material in your head. It may sound lame, but you want to be able to reduce empty air and that feeling of awkwardness. Here are some ideas - siblings, future plans, travel / places you've been, current events.

2) Have a bunch of good stories to tell. Have some short stories, some long ones. If she finds that she isn't pressured to talk, she'll be much more comfortable. Stories also give a view into your personality, builds rapport for you, and shows you're an interesting guy.

3) Change venues. Have you ever met someone you wouldn't even say hi to in high school or college outside of school? All of a sudden, you're best buddies ("wow, aren't you in my english class?" or "hey don't you go to Central High?"). Every time you move form restaurant to bookstore to your apartment, you build comfort like you've known each other for a long time.

4) The obvious stuff - don't talk about exes, anything negative, politics, religion, etc.

5) Compliment her hair or a piece of her clothing or the way she smells. Don't overcompliment. Once per date is more than enough. Don't repeat your compliments. Trust me, she heard it.

6) Be decisive. Don't supplicate. Don't ask "what do you want to do?" You're the man. Plan the date, show her a good time. If confidently act like things are going well, they are.

7) Wear some "flair". Have a neat lighter or pen she can comment on to give her an free conversation topic. Make sure you have good stories to go with your flair. "I got this lighter from my grandfather before he went to the war blahblah"

8) Still not enough conversation material? Here is the ultimate lifeline:
http://theobvious.typepad.com/blog/2005/05/the_cube.html
The girls LOVE this one. Trust me. You are building a great emotional connection.

9) Touch her non-sexually. On the shoulder, elbow, etc. It might be awkward at first but don't act awkward when you do it. Just put your hand on her back or shoulder when you suggest you shuld change venues. Rub her shoulder when she's telling a sad story, etc.
posted by lpctstr; at 4:47 PM on October 29, 2005 [1 favorite]

For some reason, Opera always crashes when I'm writing answers. Maybe it has to do with the live preview window or something.

Anyways, here is the advanced stuff.

Dating Conversation 301.

You want to escalate your conversation. She can trade facts with anyone. You can start with small talk (weather, school, places, foods, movies, music) but you need to escalate to personal topics. Find out what makes her tick. Tell her stories that reveal your weaknesses (as long as they're not terribly big weaknesses). You want to build a deeper bond than "oh, I know what food he likes to eat". The highest level of connection (and the best) you can make is discussion of your dreams and life and what makes you happy. You can't start talking about this stuff when you first meet, so that's what the small talk is for.
posted by lpctstr; at 5:02 PM on October 29, 2005 [1 favorite]

4) The obvious stuff - don't talk about exes, anything negative, politics, religion, etc.

disagree totally
talk controversy, be opinionated! it always helps; if it turns her off, you can be sure you don't like her that much; if it turns her on, then, well... and loudness, opinions, and so forth lighten conversations, make room for more, etc.
posted by yonation at 5:06 PM on October 29, 2005 [1 favorite]

From the 48 Laws of Power: "A clever trick, often used by the ninetheenth-century French stateman Talleyrand, is to appear to open up to the other person, to share a secret with them. It can be completely made up, or it can be real but of no great importance to you - the important thing is that it should seem to come from the heart. This will usually elicit a response that is not only as frank as yours, but more genuine - a response that reveals a weakness".


Now in your case, you are not looking for a weakness, but you do want her to open up. I have used the above technique with great success. I simply take off my social mask and shield and tell my conversational partner something I usually keep in my diary or a thought I would normally keep to myself. A side-effect of this technique is a small dose of catharsis.
posted by jasondigitized at 5:07 PM on October 29, 2005

The "Share with her" works best. Just don't OVER-share. ;)
posted by SpecialK at 5:24 PM on October 29, 2005

Sharing a secret, as mentioned above, works well for me. Stories work well to. Some people are just natural storytellers, but if you think ahead of some interesting things that have happened to you, you can still pull it off.

People watching can stimulate conversation. "Do you think that couple over there are friends, married, or dating?" Out at a restaurant you'll have plenty of material, and it's an interesting insight into how you both think.

Reminiscing is good. Granted, you'll only have one shared experience to reminisce about, but every little bit of genuine conversation, even if you've planned it ahead of time, will help open her up for the real talking. Also, depending on the tone of the date you could get a bit romantic and use the party as a reason to discuss why she caught your eye in the first place.

If you've tried everything and the conversation still stagnates, it's probably time to head home (alone). If you still like her and still think it's just a case of her opening up, be a bit self-deprecating about how first dates are always nerve wracking and that you'd love to get to know her more. She may feel a little more at ease if she gets the impression that it wasn't all effortless for you either. Based on your question, it probably wasn't

I'm hardly an expert, but my current girlfriend is quite shy so I've been through this before. One thing I can tell you with certainty: don't do this.
posted by teem at 6:48 PM on October 29, 2005

Listen to lpctstr, based on that post I'd totally date him. And don't underrate listening as a conversational skill- 'tis the most important of all.
posted by fshgrl at 6:58 PM on October 29, 2005

Two things: confidence really helps and be yourself, if he/she's not into you, move on. It's not that hard.
posted by brokekid at 8:02 PM on October 29, 2005

Damn.... teem beat me to it.
posted by spilon at 9:34 PM on October 29, 2005

Yeah your date could pretty well be me too. A few thoughts...

I would definitely second the "activity". I open up a lot better when there's something to talk about. When the focus is just on me, I freak out a bit. Doing something one person knows about and the other doesn't has always worked for me. With my current boyfriend, that meant him teaching me to play pool (one of his interests), and me taking him around an art museum (one of mine). Something where you can laugh (I proved to be very bad at pool, and the art was very very bad) is really good. I don't recommend movies because you spend so much time just sitting next to each other in silence. I like plays because at least you may have an intermission to talk a little. If you can do the activity first, and then go to dinner or for drinks, it gives you something to refer back to then.

We got a lot of good conversation in while driving in the car. I didn't have to make eye contact and he wasn't looking at me, so I didn't think as much about what I was doing and could think about what I was saying a bit more. If you can work out some way to go somewhere that takes a little while to get to, it might be good. Or it might be incredibly awkward.. you do have to come up with conversation topics.

If you rubbed my shoulder on the first date I would be paralyzed with fear. I'm sure some shy girls would be better with touching than I am, but I would have a really hard time with that one and probably send off some really strong "go away" signals even if I liked you. A warm smile would do it for me. I love being touched now, but it takes longer for me to let someone into my space. She may differ here though. Might see how she responds if you touch her once, whether she shrinks back or anything.

On controversy... the first time I really opened up to my boyfriend was when we talked about religion, so I can't agree with the recommendation to avoid it. Worst that you'd get from me would be a one word answer, and you're getting that anyway, so no big loss as long as you don't say anything blatantly offensive.

Talk about what you're interested in. My boyfriend reads a lot of science articles, and he went on and on (excitedly) about some he'd read recently. I guess it might have bored some people, but I liked that at least one of us was talking, because I've dealt with that awkward silence crap so much in my life. Having someone interested in sharing with me was a nice change. That said, give her space to slip in to the conversation. Watch for signs that she might want to say something and pause long enough for a reluctant person to get it in.

If she gives a one-word response, don't take it as a sign that she's not interested in the subject - ask another related question, or one for clarification. If she closes that one off as well, move on to something else. Don't assume that her brief answers mean that she doesn't want to talk to you. They might, but since you're not worried about her interest in you, it's more likely that they don't.

Oh, and don't tell her you're going to get her to talk more, or point out that she's talking more if she is. She's probably got more than enough self-consciousness.
posted by jheiz at 10:08 PM on October 29, 2005

how can I make sure the conversation flows well on a first date?

Probably the most important thing to do to open up the conversation is not be the one talking most of the time. Listen to what she says respond honestly, but try to ask questions instead of making statements.

If she says, "I like watching [your favorites sports team]", don't follow up with your impressive knowledge of the topic. Instead, ask simple, easy to answer questions, like "Did you see the game [whenever it was]?", "Do you see many games?", or something similar.

Ideally, what your doing is building trust and confidence that you're not going to embarrass her, confront her, or otherwise make her uncomfortable. It's social engineering, so be aware that what you're doing to get her to talk should not indicate to you that she's interested in you, but your confidence game has worked.
posted by sequential at 10:46 PM on October 29, 2005

Remember to smile at her warmly when she does talk (unless what she's saying shouldn't elicit smiles), or otherwise offer positive reinforcement for opening up.
posted by Soliloquy at 11:13 PM on October 29, 2005

Just an idea: Bowling. No ... seriously. I used to be super shy and quiet on dates too, because small talk and just talking one on one made me anxious when I didn't know someone well. The best first date I ever had we went bowling (he was shy too), and even though we both sucked at the game, we ended up laughing and talking a lot more than we would have had we sat down in a restaurant or bar. Some bowling places have nights when they have fog and black lights and music playing like a nightclub which can be a lot of fun too. I've suggested this to a few of my shy male friends, and while they initially thought the idea was silly, when they implemented it, they said it worked out great.

There's lots of great advice in this thread, like sharing a secret or a story that exposes one of your minor weaknesses, and if not bowling in particular, some sort of activity that doesn't require talking and maybe is a little physically active and competitive is always a good idea for shy quiet folks.

Good luck! :)
posted by Orb at 11:44 PM on October 29, 2005

Nothing personal, but lpctstr; sounds like my date nightmare.

1) Plan a bunch of talking material in your head.

Completely disagree. The more spontaneous the date the better.

2) Have a bunch of good stories to tell.

Nothing more boring than someone who keeps telling stories unprompted.

3) Change venues.

No. Unless she wishes to choose a place (and you'll offer to let her pick prior to being together), pick a place that you are familiar with (the menu, the atmosphere, the sound volume, the staff) so that at least one of you is in your element. Do your best to pick a place that is interesting and quiet enough that you can actually hear each other without straining. A good food/drink menu helps, also. Do not change venues--the worst that can happen is you'll get into 'I dunno, where do you wanna go?'

That said, have a backup in case the place you pick has a sudden "shit, didn't know that" event (like a live DJ or a loud party booked). Make it close to the original choice. Have this backup even if she picks the venue (do your homework) for the same reason.

4) The obvious stuff - don't talk about exes, anything negative, politics, religion, etc.

Completely disagree. Do not censor yourself. You want to be honest about who you are if you want her to open up. That means talking about the things you like to talk about, regardless of what they are. If you're a politics nut (or film nut or whatever) and hide that, she's only going to find out later when it's "too late". Give her the opportunity to judge you as you want to be judged (who you are), not who you're second guessing she wants you to be.

The one exception is if you're on the rebound. Do not talk longingly about your last girlfriend. Talking about exes in general is perfectly fine, though. Women like men who have had experience dating. It says a lot about them if they can talk positively about their exes (I'm friends with all my exes but 1--women like that about me, for the most part--shows I'm not just pretending not to be a dick).

5) Compliment her hair or a piece of her clothing or the way she smells.

Compliment her if it occurs to you to do so. Personally, I never do this on a date. I do, however, compliment someone later (if I think they deserve it) so that a) it doesn't make them uncomfortable on the first date when they may already be nervous; b) to show that I remembered what it is I'm complimenting them on. IMO, a compliment at a later date seems more sincere as it means the person really made an impression. Many people do not like compliments (myself included) and HATE having 'strangers' pay them. Don't find out that she's one of these people the hard way.

6) Be decisive. Don't supplicate. Don't ask "what do you want to do?" You're the man. Plan the date, show her a good time. If confidently act like things are going well, they are.

I agree with this but don't understand the last sentence.

7) Wear some "flair". Have a neat lighter or pen she can comment on to give her an free conversation topic. Make sure you have good stories to go with your flair. "I got this lighter from my grandfather before he went to the war blahblah"

Flair? Um, flair's a negative. Always is. Instead, I'll suggest that you actually dress nicely and wear good shoes (women love good shoes!). A lighter, though? Means nothing to me except that maybe you smoke and I don't date smokers. :)

As for the story thing... again, if it ain't true/honest, don't tell it. Impressing people with lies is a stupid thing to do. (Not suggesting you were saying to lie, but not everything that impresses has a story--please don't invent one.)

8) Still not enough conversation material? Here is the ultimate lifeline:

Mary, Mother of God, no! Unless she's still in her teens this is something she'll tell her friends that you did just before sticking her fingers in her throat.

9) Touch her non-sexually.

For chrissakes, KEEP YOUR HANDS TO YOURSELF!

Until it's time to kiss goodnight, do not touch her unless she touches you first.

My main advice to you is:

a. Be confident. Always.
b. Be interesting.
c. Be interested.
d. Be aware.
e. Look confident, interesting, interested, aware, and inviting.
posted by dobbs at 1:19 AM on October 30, 2005 [2 favorites]

About compliments — in the early stages it's better to compliment a woman on an item of her clothing than on her physical person. You're complimenting her taste and making her feel that you really see her without coming across as lecherous. Then later when things get physical you can feel free to enthuse about her physical attributes.
posted by orange swan at 4:45 AM on October 30, 2005

I don't know dobbs- I disagree about the exes thing. A first date is like an hour, two, right? If you can't go that long without having to bring up your ex in conversation, I would get the idea that maybe you're not ready for a new relationship. Case in point: I went on a blind date with a guy who brought up his ex, oh, three or four times. How they talk on the phone every day, how she's like a sister... It was just too much, and if I had liked him, it would have been a big turnoff. I think everyone likes to know that the people they're dating has had experience, and that they can stop dating someone without setting things on fire or a restraining order, but for the first date, I think the topic of exes is best kept to oneself. But that's just me.
posted by ThePinkSuperhero at 5:29 AM on October 30, 2005 [1 favorite]

The complimenting thing is good in my book. Even just "You look pretty/nice/whatever" will make your date feel good about herself, which in turn will probably bolster her self-confidence a bit. Don't go overboard though.
posted by Lotto at 6:25 AM on October 30, 2005

I'd listen to Quietgal and jheiz—they obviously know whereof they speak. Be confident, don't be pushy, go with the flow, and good luck!
posted by languagehat at 6:33 AM on October 30, 2005

Here's my notion. Go to an open mic night or some kind of comedy improv-- something interactive where you can share whispered bon mots with one another. There will always be something to talk about-- even if the performers bomb utterly, you can definitely joke about it. And the need to whisper, or to speak in low voices, means lots of physical closeness without making actual contact.

Art gallery openings and the like are a close second, but tend to be a little bit heavier in terms of conversation. It's fun to talk about the artwork, and the other poseurs-- oh yeah, we're one of them. Again you have to be close and discreet-- hey do you think that she's the artist? Can you believe that he painted that?

Teem sounded a similar idea. Just wanted to flesh it out a little bit. Once the conversation starts to flow from the events of the evening, you can go with it!
posted by Scooter at 8:11 AM on October 30, 2005

orange swan, I agree to the extent that if you must compliment someone because you feel you should (rather than because you genuinely want to) than, yes, comment on a coat, shoes, whatever. But scent? That's stalker-esque in my book. To me, compliments should never be used to get into someone's good books. Compliment someone if the thing that you're commenting on genuinely strikes you.

TPS: I agree and disagree. Anyone who brings up their ex 3 or 4 times in 2 hours has issues, in my book--which is what I meant by "Do not talk longingly about your last girlfriend", though I guess I should have said "past girlfriends" to include 'em all. Note that I'm not suggesting one has to bring up the topic but I simply disagree that the topic is "off limits".
posted by dobbs at 8:17 AM on October 30, 2005

I've had more than one date where my last relationship is actually the thing that the girl asks me most directly about. As if she's going to predict the course of her possible relationship with me on that basis, or something. Even more common is the single question as to whether I have remained friends with my exes, as if she's trying to ascertain whether, worst case scenario, we'll end up as friends. So, you never know what she really wants to hear, unless she asks, and if those are the sort of things she asks, well, it's not a good sign in my view, but YMMV and all that.
posted by bingo at 10:21 AM on October 30, 2005

In my book, asking about exes is rude. I consider it's none of my business, and so never ask. If the ex is an issue (like oh, say, the exwife is still living in his house), you'll be sure to hear about it anyway.
posted by orange swan at 10:43 AM on November 7, 2005