How to Handle a Second Date

Co-authored by Laura Bilotta and Hannah Madden

Last Updated: May 26, 2022 References

You’ve gotten through all the first date jitters, and you know you and your date have a connection. A second date is a great way to strengthen your bond and figure out if you two actually have potential together as a couple. In this article, we’ll tell you everything you need to know before your second date to make sure it goes smoothly (and to help you land date number three).

1

Plan a date activity that gets you both moving.

Pick something active that still allows for conversation. Do something totally different than what you did on the first date. Hiking, walking through a park, swimming, or even lightly jogging are great second date activities. You can fill any awkward pauses by focusing on the activity at-hand, and if you want to end the date early, you can say that you’re too tired out to continue.^{[1]
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- You could also try mini golfing, bowling, having a picnic, walking along the beach, or visiting a rooftop bar.
- Just avoid anything that would prevent you two from chatting, like a crowded bar or a movie theater.

2

Wear something cute and casual.

The second date is when you can let your hair down a bit. If you dressed up for your first date, you can keep things a little more casual on the second one.^{[2]
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Research source} Pick an outfit that fits you well, and make sure you feel your best before you head out the door.^{[3]
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Expert Source

Laura Bilotta
Dating Coach & Matchmaker
Expert Interview. 4 March 2020.}
- Think about what you’re doing on your date, too. For an afternoon stroll through the park, jeans and sneakers are probably your best bet. For a night out at a bar, your best slacks or a flowy dress might be more fitting.

3

Greet your date with a hug.

By now, you know your date enough to hug them and say hello. When you both show up to the date, give them a quick hug, and a peck on the cheek if you’re feeling it. This shows that you’re willing to break the touch barrier with them, and that you don’t mind a small amount of PDA.^{[4]
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- If your date flinches or pulls back from your hug, they might not be comfortable with you just yet. That’s okay—just give them time.

4

Dive a little deeper with conversation.

Move past the small talk into genuine topics of conversation. On your first date together, you probably learned all about your date’s job and education. On the second date, it’s time to ask your date some deeper questions—try talking about their goals, their childhood, and their family.^{[5]
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- “Did you grow up around here?”
- “Where do you see yourself in 5 years?”
- “Are you close with your family?”
- “What do you get up to on the weekends?”
- “What’s your favorite way to relax?”

5

Show them you're a great listener.

Let them tell you about themselves so you get to know them more. As you two chat, make eye contact and nod along to show your date that you’re listening.^{[6]
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Expert Source

Laura Bilotta
Dating Coach & Matchmaker
Expert Interview. 4 March 2020.} Try to get a good back-and-forth going—you ask your date a question, then your date asks you a question. Avoid dominating the conversation, since that can make your date feel overwhelmed.^{[7]
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- You can also ask your date follow-up questions, like, “Interesting, can you tell me more?” and, “What do you mean?”

6

Embrace awkward pauses.

There might be some lulls in the conversation, and that’s okay. A little bit of awkwardness is all part of getting to know someone—your date will understand! Don’t feel like you have to fill the silence 100% of the time. Sometimes, riding it out is the best way to get through it.^{[8]
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- You could even make a joke about it. “Wow, that sure was awkward, wasn’t it?”

7

Be yourself.

Dating is all about seeing if you two are compatible. Don’t worry about putting on an act—let your date see the real you.^{[9]
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Expert Source

Laura Bilotta
Dating Coach & Matchmaker
Expert Interview. 4 March 2020.} Make goofy jokes, talk about your day-to-day life, and focus on making a genuine connection with someone cool.^{[10]
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- As you get more comfortable with your date, this will get easier and easier.

8

Get a little flirty.

Let your date know that you’re definitely interested in them. A second date means that there was initial attraction on both sides. When you’re with your date, let them know that you’re still into them by giving them cheeky compliments throughout your time together.^{[11]
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- “I really like your smile. It lights up a room.”
- “When we met up for our first date, I thought, ‘Wow, I can’t wait to learn more about this person.’”

9

Break the touch barrier.

Show your date that you’re comfortable by lightly touching their hand or arm. Throughout your date, you might have the opportunity to grab your date’s hand or pat them on the shoulder. Doing this will show that you’re interested in them, and it will bring you two closer together as well.^{[12]
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- You might pat them on the shoulder as you laugh at their joke, or grab their hand as you walk through a park.

10

End the date with a kiss, if you want to.

By the second date, most people are ready for some physical contact. If you and your date have had a blast together, they’re probably okay with a light smooch.^{[13]
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Expert Source

Laura Bilotta
Dating Coach & Matchmaker
Expert Interview. 4 March 2020.} When you say goodbye, lean in slightly and give your date a kiss on the lips, but keep it short. Tell them you had a great time.^{[14]
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- “This was so much fun. Thanks for taking me out tonight. I’d love to do it again soon.”
- “I had a great time with you! Let’s set something up for next week.”
- For most people on a second date, a kiss is as far as they’ll want to go in terms of intimacy. There aren’t any rules about when you two should have sex, but don’t worry about doing anything you don’t want to do.

11

Text them later about how much fun you had.

Let your date know that you’re interested in seeing them again. If you had a really great time, shoot your date a quick text and ask them when they’re free to hang again soon. Don’t worry about any “rules” for how long you should wait—if you want to see your date again, tell them that!^{[15]
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- “Hope you got home safe! I had such an amazing time. Are you free at all this weekend?”
- “Thanks for walking me home tonight. Want to get together next week for drinks? I’m free on Tuesday.”

Expert Q&A

Question

How do you date a shy person?

Laura Bilotta
Dating Coach & Matchmaker
Laura Bilotta is a Dating Coach, Matchmaker, and the Founder of Single in the City, her dating and relationship coaching service based in Toronto, Ontario, Canada. With over 18 years of experience, she focuses on helping singles date more intentionally, encouraging them to let go of negative patterns so that they can attract the love that they deserve. Her experience, skills, and insights have led to thousands of successfully united over 65,000 singles through events and one-on-one matchmaking coaching sessions. She has been the host of The Dating and Relationship Show on Global News Radio 640 Toronto (AM640) for 6 years and is known as The Hookup Queen of Clubhouse; her popular singles club, Single in the City, has over 95.5K members who regularly join in weekly dating and relationship-focused rooms.

Laura Bilotta

Dating Coach & Matchmaker

Expert Answer

A shy person usually needs to build trust with someone to open up. Do an activity rather than a sitting down one on one date with them. It will allow you to do something you both enjoy and get to know each other.
Question

How can you impress a girl on a date?

Laura Bilotta
Dating Coach & Matchmaker
Laura Bilotta is a Dating Coach, Matchmaker, and the Founder of Single in the City, her dating and relationship coaching service based in Toronto, Ontario, Canada. With over 18 years of experience, she focuses on helping singles date more intentionally, encouraging them to let go of negative patterns so that they can attract the love that they deserve. Her experience, skills, and insights have led to thousands of successfully united over 65,000 singles through events and one-on-one matchmaking coaching sessions. She has been the host of The Dating and Relationship Show on Global News Radio 640 Toronto (AM640) for 6 years and is known as The Hookup Queen of Clubhouse; her popular singles club, Single in the City, has over 95.5K members who regularly join in weekly dating and relationship-focused rooms.

Laura Bilotta

Dating Coach & Matchmaker

Expert Answer

Be on time. Be a gentleman, open the door for her, pull out her seat, and let her order first. All this can be very charming.