How to Plan the Perfect First Date

Here’s the problem: you are good. First dates are bad.


“First dates are horrible, they are. It’s awkward, usually, and uncomfortable. And it’s like, ‘get me out of here’,” says Michelle Frankel, President and Chief Love Officer at NYCity Matchmaking. That’s bleak, but the numbers support it. Nancy Slotnick, CEO of Matchmaker Cafe, says that only one in 10 first dates leads to a second date. And, to make matters worse, a part of what’s holding back success may be you. “People don’t think of how they’re coming off,” Frankel says. You talk too much? Narcissist. Plan a date close to home? Selfish. Don’t pay? Rude (and poor). Plan a date day of? Juvenile.

So there’s your problem: you are good. First dates are bad. There’s a gap that needs to be bridged. You need to take a scenario that can be intimidating, difficult, confusing and awkward and make it fun, captivating, enjoyable and memorable. You need a situation that fails nine times out of 10 to work. You can rely on the magic of chemistry and a small prayer, or you can go to the experts.

Frankel, Slotnick and Maria Avgitidis, founder of Agape Match, help guide the misguided down the path to finding love. Using the collective knowledge of all three and their tens of thousands of successful first dates (on to the second date!), we put down some helpful markers to lead your time together with that special someone.

1 Call, don’t text. Or, fine, text (but that’s weak). Call it old-school chivalry, but both Frankel and Avgitidis see a phone call as a way to set yourself apart. The call allows a level of intentionality, can keep communication clear, and often saves time. On the other hand, texting can be totally fine if necessary; but, if the opportunity presents itself, the call puts you in a better situation for success.

2 Plan ahead. And give options. “The first piece that people underestimate is scheduling”, Slotnick says. You’re busy. Your date is busy. And life is tough. So, plan ahead. Slotnick recommends offering three days to set up a date — a subtle “You free Tuesday, Thursday, or Sunday?” gives options, without being too open ended. Once the day is locked, consider some date options. Frankel’s a big advocate for low-pressure activities, like a walk in the park or a bar with a pool table. “You learn more about the person when you’re doing something”, she says. “And if you like the activity, you’re going to have fun anyway.” If what’s fun for you is drinking, keeping it to drinks is fine. You can offer options for meeting up, or just pick a place. “Most people don’t care what the plan is”, Frankel says, “they just appreciate when there’s a plan.” It’s also courteous to plan a spot near your date’s home, if possible.

3 Don’t monopolize your date’s life. Here come the Don’ts: Don’t set the date for a Friday or Saturday night; don’t pick a location that’s inconvenient for your date; don’t book a full dinner; don’t go somewhere exceptionally loud; don’t plan a date for after 10:00 p.m.

Okay. So there’s that. Let’s call those guidelines more than rules. The spirit is that this is a first date. It’s not a big deal. It’s a 45-minute-to-an-hour span to meet, see if there’s something there. Keep expectations low, be courteous to your date’s schedule and life, and be cognizant of what the first date is: just a time to connect. Meet. See how things go.

And as for that 10:00 p.m. meet up time? Reeks of hookup. Slotnick says that advanced planning “shows relationship-mindedness”, so, plan according to your intentions.

4 Don’t be awkward. Entering into the date, there are some directions that can improve outcome, starting with having realistic expectations and not conducting an interview. You shouldn’t come in with a checklist. See where the swirling wonder of chemistry can take you. Or, at the least, appreciate the person for meeting you in this environment. And even if you’re not jiving, don’t shut down. Be a good person. Be gracious.


As for specifics, Avgitidis recommends a perpendicular seating position if possible, so you can be close without making things interview-esque. She also covers the usual conventions: reign in politics and religion, and don’t bring up past relationships. “It’s just irrelevant”, Frankel adds, and she says to make sure conversations are two-sided. People often get nervous and talk too much or fall silent. “Let conversation be organic”, Avgitidis says. Slotnick adds some more blunt advice: “If you’re uncomfortable with conversation, you need to become a better conversationalist.” Compliment. Be genuine. Don’t be an absolutist. Be confident, polite, positive. Don’t check your phone.

The experts’ final, unanimous point was to always pay. It’s a ritual that may feel antiquated, but paying is what’s expected if you set up the date. When the check comes, slide it over to your side of the table. If your date offers, graciously decline. You initiated, you can afford it.

5 Plan the second date. If things are going well, it’s cool to hint at or plan a second date. You don’t have to be mysterious. “Build upon the chemistry”, Slotnick says (she also advocates for the first-date kiss). Follow up the next day if you’re interested. “Say, ‘I had a great time, I want to go out again'”, Frankel says; she advocates for scheduling the second date soon after the first. Letting things sit shows a lack of interest, so capitalize on the momentum and see where the magic will lead.

Our Panel of Matchmakers and Dating Experts: Michelle Frankel, President and Chief Love Officer at NYCity Matchmaking | Nancy Slotnick, CEO, Matchmaker Cafe | Maria Avgitidis, Founder, Agape Match.

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