So you had an amazing time on your first date and your second one is right around the corner. Now that you know you have a great connection, you can flirt even more and really hit it off on your second date. Even if you still have some leftover jitters from going out the first time, it’s easy to show your date that you’re interested in them. Keep reading for what you need to know while you’re out so you can land a third date with them!

This article is based on an interview with our dating coach, Candice Mostisser. Check out the full interview here.

8

Give them a compliment.

  1. Your date will feel flattered when you point out what you like about them. While you can always mention something about how they look, you’ll get a lot more brownie points if you compliment your date’s personality or achievements. Just be careful not to overdo it or say anything that’s too sexual since it could make your compliments seem less genuine.
    • “You look absolutely stunning in that top!”
    • “Wow, you rocked that karaoke song! Why didn’t you tell me you had the voice of an angel?!”
    • “You’re so easy to talk to, I feel like I could open up about anything with you.”
9

Open up with deeper conversations.

  1. Your date will love that you want to get to know them even better. While the first date is about breaking the ice and seeing if you have fun together, use your second date to see how compatible you’d be in the long run. Start asking about things like their family, their values, what they want from a relationship, and what they want from their future. Be sure to answer the questions too so the conversation stays balanced.[2]
    • “What is something you’re hoping to achieve in the next 10 years?”
    • “How do you get along with your family?”
    • “What’s the most important thing in a relationship for you?”
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11

Ask follow-up questions.

  1. Asking for more shows you’re listening and want to learn about them. After your date finishes talking about something, try to dig a little deeper rather than changing the subject. Bounce off of what they just said and keep chatting about the topic so your date feels like you care about what they have to say.
    • “That’s so neat you grew up in a small town. What was your favorite thing to do there?”
    • “It sounds like you’re really close with your family. How often do you get to see them?”
    • “Skiing is one of my favorite hobbies too! What’s the best slope you’ve ever been on?”
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13

Playfully tease them.

  1. Poking fun is a sure sign that you’re into your date. When you tease your date, you’re testing out if they’re having fun and have a good sense of humor. Just be careful not to say anything that could offend your date or be taken the wrong way since it could be a turn-off.
    • “Gutter ball? I thought you said that you were good at bowling!”
    • “If you’re a musician, you won’t have any problem singing me a love song, right?”
    • “Was that your way of hitting on me? Because it was super cute.”
    • If your date does get offended, apologize quickly and try to move on to a new subject.
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14

Make loose plans together.

  1. Tentative plans show your interest in seeing each other again. You don’t have to set an exact time and date for seeing each other. When your date mentions something that you’re both interested in, suggest a theoretical plan so your date pictures you with them in the future.
    • “My friends tell me I’m the best chef! We should find something to make for dinner and cook it together sometime!”
    • “I’m so glad we both love going to the farmer’s market! Wouldn’t it be fun if we went together and sampled all of the food?”
    • “If you think you’re so good at basketball, you should try taking me on 1-on-1 sometime soon!”
15

Try ending on a kiss.

  1. A quick smooch can seal the deal. When you feel like the date went well and your date is into you, show that you’re interested by looking at your date’s mouth and lightly touching them. Then, just be courageous and try moving in for the kiss. If your date feels the same connection, they’ll lean in for it too and end your date on a romantic note.
    • If your date rejects the kiss, respect their space. Maybe they don’t like PDA or they may not be ready for that much physical contact yet.
    • Even though you can usually tell from your date’s body language, it can be really courteous to ask for their consent before kissing. You could say, “I’ve had such an incredible time tonight. Would you mind if I kissed you?”
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About This Article

Candice Mostisser
Written by:
Dating Coach
This article was written by Candice Mostisser and by wikiHow staff writer, Hunter Rising. Candice Mostisser is a Dating Coach for NYC Wingwoman LLC, a date coaching service based in New York City. 'NYC Wingwoman' offers matchmaking, wingman/wingwoman services, 1-on-1 coaching, and intensive weekend bootcamps. She specializes in coaching others on best practices and strategies to succeed on first dates and in the online dating world. This article has been viewed 20,866 times.
4 votes - 100%
Co-authors: 5
Updated: July 30, 2022
Views: 20,866
Categories: Flirting | Dating
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