Coupled With D&S

Real, nonjudgmental advice about dating, sex, love, and life from a thirty-something couple that has seen it all over thirteen years.

Trust us. We live in Brooklyn. (Joking. Kind of.)

The Follow Up: Trouble Negotiating that Second Date

The Question

David tried, unsuccessfully, to woo some girl.

David tried, unsuccessfully, to woo some girl.

A straight San Franciscan in his 30’s wrote to us about the right way to follow up with a woman. “I have no problems getting the first date, but I seem to be striking out lately when it comes to getting the second date. Usually if I feel like the first date went well, I’ll ask if they’d like to get together again. They usually say yes when I ask them in person, but I often find that not to be true and we don’t end up meeting again. It varies how I follow up. Sometimes I’ll call, sometimes I’ll text. Which do you think most women prefer? It’s usually midweek the following week when I’ll contact them to see if they want to go out again. Is that too soon? I don’t think wanting to see someone the following week is too soon, but maybe I’m wrong. Lastly, I’ve been going by a hard rule that if they don’t get in touch with me after the first time I contact them, then I don’t bother. Is persistence the key here? I don’t want to come off as desperate or clingy when trying to get that second date. There’s gotta be some kind of fine line to walk there, right?”

The Consensus

This is a fairly simple one, and we’re both in absolute agreement, so we’re going to answer together. Let’s start with what you’re doing well. You’re getting first dates, which is great. We all know that it’s hard enough to get a response to a first message, let alone an actual date.

See me again? We’re not so keen about asking women on the first date whether they’d like to see you again. Yes, women likely know after a few minutes or a few drinks whether they’re interested or not. However, asking outright isn’t helping you and might even hurt you. It’s a bit of a challenge to ask a woman face to face, before she’s really digested how she feels about you, whether she would like to go out again. We live in a society where women are supposed to acquiesce to men and make them feel comfortable in social situations, so you’re could get a lot of false positives just to avoid making you feel bad. You also have to consider that there are a lot of aggressive and unstable guys out there, and women risk witnessing a tantrum or even verbal or physical assault when they upset a man they don’t know, so there’s a real incentive to avoid conflict. If a woman is on the fence about you after one date, or if she’s someone who really does need time to digest her feelings, then putting her on the spot might actually tip her against you. That said, someone who’s really into you will probably say yes and mean it. We recommend just emphasizing what a great time you had, thanking her for the date, and leaving the rest to your timely follow up.

Do women prefer text or a call? Text, clearly. A text message gives you time to think about what you want to say. It lets the responder answer on her own terms … or fade away if that’s what she’s most comfortable doing. We think some of the psychology here might be related to the conflict-avoidance tendencies we mentioned in the above paragraph. We don’t think complete conflict-avoidance is a good basis for building a relationship (though you can’t run a relationship no holds barred either), but neither you nor your first dates owe each other much at this point, and leaving space for a polite decline or a non-answering decline is sometimes the most humane option.

Is midweek the following week too soon to contact a woman to see if she’d like to go out again? Seriously? No. In fact, that’s WAY too late. In the short attention-span, low investment world of online dating, someone who liked you a little bit and might have been game has probably been on other dates and practically forgotten about you already. If you wait close to a week or more before writing, she’s likely to think that you didn’t like her or, worse, that you’re indecisive and insincere. Send a message the next day. Tell her specifically what you enjoyed about the date or her (refer to something you did together or learned about her), and ask her out, preferably for something you know that she’d like (e.g. rock climbing if she’s into that, an exhibit or museum if that’s her thing, a concert in a genre she likes, food from a region she loves, etc.). Give her a date-range. This should be a relatively short, condensed message, however. Two or three sentences max. Loved meeting you last night. Your story about your month in Spain made me want to go too. Since I can’t go right now, could I take you to tapas next week instead?

Is it a good policy to not bother with a woman who hasn’t contacted you back? If we’re talking about a first date, yes, absolutely. Let everyone save face and end it here. If there was a second date or more, however, you could try one more time with a text message. Don’t be too self-effacing or apologetic, but give an out too and be prepared to take silence or no for an answer. Thought I’d give it one more shot …

Now that we’ve solved all your follow-up woes, all you have to do is be incredibly handsome and charming, and you’ll have more second dates than you can handle. Let us know immediately via text, whatever happens.