How to Turn a First Date Into Many More

It happens to the best of us. (Especially since, as Looking points out, dating can be very hard.) We find ourselves having a string of first dates, one after the next. For some unknown reason, we can’t seem to get a second date. Either the texting fizzles out, or we misread how interested he actually was. Who knows? It could be one of a thousand reasons.

If you find yourself having a bunch of first dates, when what you really want is to be having more dates with the same guy, look no further. Here are 4 tips to help you turn that first date into many more.

1. Talk about something meaningful

Do you find yourself having the same boring conversations on every first date you have? “What do you do?” “Where are you from?” “Where did you go to school?” “How long have you lived here?” If you’re talking about nothing interesting, than your date won’t think that you are interesting. Take a risk. Expose something personal about yourself that will lead to an in-depth, meaningful conversation. Ask tough questions. Discuss societal issues, politics, and your most embarrassing drinking story. Be interesting by saying something interesting. (And FYI, you know the date is screwed what you get to the point where you start asking, “What does your sister do?”)

2. Try to end the date on a concrete note

At the end of the date, instead of going through the usual, “We should do this again sometime,” make your intent that you want to see them again clear. I like to open myself up to rejection. I say something along the lines, “I know you’re busy with [X], but I would definitely love to see you again sometime next week if you’re free.” This gives them an “out,” which is good; they can say they’re too busy. Or, conversely, you can schedule a second date right then and there. Don’t end first dates in the gray area if you don’t have to. 

3. Don’t have sex with them on the first date

ALRIGHT. EVERYBODY CALM DOWN. I usually sleep with guys on the first date, and there’s absolutely nothing wrong with that. But if you notice that you tend to sleep with guys on the first date, and afterwards, they don’t wanna see you again...then it’s time to withhold sex until you get to know the guy a little bit better.

4. Don’t wait to text them after

If you had a good date, and you like them, text them the next day (or if you don’t think it’s too aggressive, even that night). There’s no reason to play games. You shouldn’t wait 72 hours before texting, “Hey are you free again this week?” If you like them, make that clear, and try to see them again sooner than later. If you wait, something may pop up for him, or he may already be excited about the next guy. Once the ball is rolling, you want to keep it rolling.

There you have it! Follow these tips, and you before you know it, you’ll be rolling in second, third, and fourth dates.