How To Get a Second Date

By Eric Helmsley | | Dating
How To Get a Second Date

Just because the other person said yes to a first date—or maybe they asked you?—a second date is not guaranteed.

Far from it. First dates are very often underwhelming, and if they’re not outright bad, sometimes they’re just… fine. Which can make it hard to know how to proceed. Here are eight tips for asking for a second date that may help boost your chances.

1. Ask during the first date

Connell Barrett, a dating coach who authored “Dating Sucks but You Don’t,” suggests asking for another date while it’s fresh on your minds. “I’m a fan of asking for a second date during the first date,” Barrett said, “assuming you’re both having fun.”

It may seem like a bold move, but one that could pay off if both of you hit it off. “Being spontaneous and showing clear interest, without resorting to game-playing, is bracingly attractive,” Barrett said.

Barrett noted the right time for this move is “during a high point on date No. 1—when you’re both, for example, laughing about your favorite scene in “Up” or connecting over your love of skiing.”

“This strike-while-the-iron’s-hot approach ups your chance for a second date because your new crush’s interest in you is peaking when you’re vibing in real life,” he said. “If you wait a few days to ask, the first-date glow may fade, making a second date less likely.”

2. Be confident and authentic

As for how to approach the moment, now’s the time to channel some inner confidence—without going overboard into fake cockiness, said Tennesha Wood, a dating coach and the founder of The Broom List.

“If you are having fun and you think the date is going well, your date likely feels the same way,” Wood said. “Assume they are on the same page when asking for the second date.”

That means smile, make a joke and keep it lighthearted but be direct and to the point in a way that feels like you—not like you’re putting on a character.

3. Show vulnerability

On the flip side, while being confident can be a great approach, if you’re not feeling insanely confident, that’s understandable. Showing a little vulnerability can sometimes be a good approach, too.

“It’s OK to admit that you’re a little nervous!” Wood said. She suggested saying something along the lines of, “‘This is going so well that I’m nervous I can’t top it with our second date, but I’d love to try!’”

Opening up about nervousness can also help you bond with your date if they experienced similar feelings. Even if they don’t, you show them a softer side of you they might find charming.

4. Pay attention to body language

If the first date is still ongoing and you’re trying to decide whether you feel confident or not, Wood said reading them—in particular their body language and how they talk about you—can be a huge cue as to their interest.

“If your date is maintaining eye contact, touching you or making inferences to things in the future,” Wood said, “they’re interested and you should just ask.”

Those are likely signs you don’t need to overthink how you ask and you can just go for it.

5. Turn a shared interest into a date

If the date ends without either of you making plans for a second date or without any clear signs your date wanted you to, that doesn’t mean it’s a dead end.

Lots of people are shy about these things, and she may not feel comfortable asking.

“A great way to ask for a second date,” Barrett said, “is to take something specific that you bonded over—a mutual love of old movies, perhaps, or rocking the karaoke mic—and use that as a second-date idea.”

He suggested saying something like, “It’s so cool that we’re both into old movies. There’s an Orson Welles festival coming to such-and-such theater. Shall we go together?” Wood proposed, “You like biking, too? I know the best trail—let’s go next weekend if you’re free,” as a good example when the first date’s still ongoing.

6. Explain why you want a second date

What did you like about your date and what else would you like to know?

Here’s how to ask, according to Barrett:

“I loved hearing your travel stories! On our next date, I’m taking you to the best hole-in-the-wall Italian restaurant to see if it can hold a candle to your favorite spot in Italy, and I’d like to hear more about where you grew up.”

7. Imply it’s a done deal

“Instead of asking for that second date, assume that it’s a done deal,” Barrett said.

Consider this playing the dating game on hard mode. It’s a move you shouldn’t pull unless the date’s going super well and you’re feeling very confident—because it can absolutely backfire.

Barrett said to make “an assumptive statement, as if date No. 2 is a forgone conclusion.”

“Say something like, ‘I know what we should do for our second date. I’m gonna take you to [fun place/thing to do]. You’ll love it.’”

“By assuming mutual attraction,” Barrett said, “you heighten the interest that’s already there because it takes a very confident person to make this assumption. And confidence is attractive.”

8. Take rejection well

On the flip side, it’s important to recognize when the other person isn’t into it and take them at their word if they say so.

Regardless of when or how you ask, if you get a no or a muted, hemming-and-hawing response that feels like a rejection, swallow your pride and accept it and don’t keep pushing.

You might have heard that persistence pays off, but too much persistence can easily veer into creepy or harassing territory.

Dating is supposed to be two people having fun with each other. If the other person isn’t excited to see more of you, take it like an adult, thank them for being honest and move on.

There are lots of other people out there, and however frustrating or disappointing it can feel to not hit it off with someone you’re into, refusing to get the hint can be genuinely scary for the other person.

When to ask for a second date

If you were paying attention earlier, you know that asking during the first date is a great option, provided it seems to be going well.

If you’re taking some time to develop a rapport—or if something bad happens threatening the very fabric of the date (movie was sold out, drink spilled all over your outfit, dinner gave you explosive diarrhea)—it’s possible your date won’t be in the mood to greenlight a second date. Asking mid-date will only worsen the vibe.

However, even if the date goes well, waiting until after it’s over to bring up the idea of a second one is perfectly fine—whether you do that as you say goodbye, text message on the way home or get in touch in the days to come.

The one thing you shouldn’t do when asking for a second date is let the silence drag out too long.

“Don’t be coy or evasive,” Barrett said. “You’re dating, not dodging Senate subcommittee questions. There’s power in candor and vulnerability. Feel free to use clear, simple language, almost like a little kid confessing a schoolyard crush: ‘I like you. Want to go out again?’ It’s not needy or desperate to tell someone that you’re interested. It’s vulnerable, yes, but there’s great strength in vulnerability.”

A short rule of thumb? Don’t wait more than 24 hours. With everyone so hyper-connected via text, email and DMs these days, your date might think you’re moving on to the next person if they don’t hear from you—or they might begin to do the same thing themselves.

How to ask for a second date by text

If you’re bringing up the idea of a second date after you’ve parted ways, most likely that’s going to happen via text. Whether you’re communicating through the app you met on, social media or email, asking for a second date often happens in writing.

Knowing how to ask for a second date by text isn’t much different from how to ask for one in person, but for Barrett, there is a subtle distinction.

“In person, let your emotions inform your words,” Barrett said. “With texting, you can craft the precise, flirty message you want to send.”

In short, rather than acting in the heat of the moment and dashing off a text without thinking about it, he suggests taking some time to write a message that properly conveys the right mood and date idea.

Disclaimer: The above is solely intended for informational purposes and in no way constitutes legal advice or specific recommendations.