First date success can be measured on three scales: strength of chemistry, degree of comfort in each other’s company, and conversational quality. While the first two factors are not something you can generally influence, conversation is something different.
By following a few simple guidelines, you can keep the dialogue flowing smoothly (unless your date is super shy or hates to talk about herself, but that’s a topic for another post.)
Ask Thoughtful Questions
Listen more than you speak. Pay attention to the direction in which the conversation is going, then ask questions that will encourage your date to open up about the things that matter to her. Be careful not to ask too many questions too quickly. Take the time to think about what she’s saying, otherwise you’ll sound like a journalist, interviewing her for an article.
Notice her body language. If she’s sharing something meaningful, she’ll probably look you in the eye as she speaks, or she might get excited and start gesturing with her hands. Follow the path of meaning and excitement she’s leading you down, and she’ll start thinking of all the ways she can open up to you more.
Share, but Not Too Much
When the time comes for you to open up, do so honestly but not excessively. If she asks about your family, go with a nice little story about how Aunt Maureen always wins at cards. Don’t delve into the all the scarring and horrific details of your parents’ divorce, or your older brother’s crippling porn addiction. (These are topics best reserved for the fifth date and beyond.)
If you’re both getting deep into personal stuff, and you’re feeling good about it, there’s a chance you’re just two over-sharers who are hitting it off, in which case go deep. Just note the tone of the evening. If her eyes start to glaze over, and she keeps repeating, “That must have been really hard for you,” you should probably rein in your sharing.
Once she’s shared all that she wants with you, feel free to point out things you have in common, but don’t be afraid to voice any differences in opinion as well. This is a very delicate move. You don’t want to insult her, or come across as a narcissistic blow-hard, but you do want to show her that you’re confident and have a mind of your own.
Try something like, “It’s great that you’ve had such amazing results with the Keto diet, but I wouldn’t try it myself. I read an article saying that it’s pretty unhealthy.” Then end with something light and funny like, “I love me my potatoes!” She’ll either appreciate that you have the guts to speak your mind, or she’ll think you’re a loser for not agreeing with her. And isn’t it best to know how these types of differences are going to be received early on?
Go Easy on the Compliments
Speaking of authenticity, only say sweet things to her if you can personally back them up. It’s perfectly fine to hold off on the compliments until you know each other a little better. If you think she looks hot, say something like, “You look great,” but don’t make sweeping and overly enthusiastic declarations about her character based on one impressive thing that she might have shared.
Saying things like, “You’re such an inspiration!” or “You’re an incredible woman!” will make you appear overeager and insincere. You’ve only just met. Reserve your judgement and save some of those big-ticket compliments for moments when you’ve experienced her greatness first hand.