How to Score a Second Date (Your Mom Agrees with Us Too)

The six cardinal rules of first dates you should know

couple on date mobile

Dating is a minefield. The rules probably feel undefined and gray in 2019, and in many ways, they are, but the things that really matter, the things that will make someone want to go on a second date, are the same as ever. With a little planning and old-fashioned manners, you’ll make the right impression. Which is to say, even if you met your special someone on an app, have communicated only through text and plan to pick them up in an Uber, asking thoughtful questions and actively listening will still go a long way. Here are the six cardinal rules of first dates that have stood the test of time.

1. Start Small

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@RLTheis via Twenty20

A five-course dinner, a Ferris wheel ride and late-night dancing sounds romantic in theory, but it’s probably too much for date number one. Pick a cozy spot for coffee or a drink or have dinner in a lively, up-and-coming restaurant—something that feels special but isn’t too serious for a first encounter. The best part about this strategy? There’s room to build. Date two can be bigger, better and, well, impossible to refuse.

2. Wear a Smart Suit

calvin klein suit
Calvin Klein

Real talk: No one can resist a man in a well-tailored suit. This has always been and will always be your best move for a first date. The trick is to style it for a fun night out, not like you’re going on a job interview. Calvin Klein’s X-fit suits are cut slim for a modern look that works just as well with a shirt, tie and dress shoes as it does with a T-shirt and sneakers.

3. Genuinely Listen

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Evgeniy Anikeev via Getty

Don’t overthink what you’re going to talk about on your date. The best way to ace the conversation is to focus less on yourself and more on your partner. That means asking thoughtful questions, listening and reacting to the answers, and letting them guide the conversation. If you do this, trust: They’ll be dying to get to know you better on another date.

4. Fine-Tune the Details

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wundervisuals via Getty

Nothing makes a beautiful suit sing like a fresh shave, a haircut or just a generally well-groomed appearance. Get your hair trimmed a few days before your date so it looks ever so slightly lived in, then give yourself ample time to get ready for the big night. Self-care isn’t just something women get to do: Take a bath, shave the old-fashioned way and do a face mask!

5. Find a Natural Segue

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@wijnandloven via Twenty20

The easiest way to set up a second date is to look for an opportunity in your conversation and then seize the moment. If your date tells you she grew up ice-skating, offer to take her for a spin at the rink sometime. If he talks about how he’s dying to see the new Marvel film, suggest you plan a movie night. You don’t need to nail down the details; just plant the seed.

6. Follow Up

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Blackzheep via Getty

Make sure your date gets home safely and then send a follow-up text the next day letting your date know how much fun you had. Not only is this the gentlemanly thing to do, but it creates an opening to ask for a second date. For example, when she jokes about how bored she is at work, that’s your opening to invite her to do something extra fun. When he says he’s buying the same suit you wore to dinner, let him know you’d love to see it on him that weekend.