How to Act on a Date (for Boys)

Co-authored by Laura Bilotta and Hannah Madden

Last Updated: February 7, 2023 References

Dating is a fun, exciting experience, but it can be a little nerve-wracking if you don’t have much experience in it. Thinking about what you’re going to say, how you're going to act, or what you’re going to wear can all feel overwhelming—but it doesn’t have to be! While there aren’t any set “rules” for dating, if you keep a few guidelines in mind, you can make sure that you and your date both have a good time as you get to know each other more.

1

Show up well-dressed and on time.

A nice outfit can make a great impression. If you’re going to a nice restaurant, you might put on slacks and a button-down. If you’re going mini golfing, jeans and a T-shirt are perfect. Make sure whatever you put on is clean and wrinkle-free to make a good first impression.^{[1]
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- If you’re having trouble figuring out what to wear, ask your friends or family for advice. They can help you figure out what you look best in.
- Spend a few minutes getting cleaned up in the bathroom before you head out on your big date. If you want to wear cologne, remember: less is more.
- you. Aim to get to your date about 15 minutes early so you don’t leave your date waiting. If you are going to be late, send your date a text or give them a call to let them know.

2

Keep your phone in your pocket.

This will help you focus more on your date. If you’re scrolling through social media the entire time you’re on your date, you can’t get to know each other. Keep your phone in your pocket or put away somewhere, and only take it out if you just need to check something really quick.^{[2]
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- If you do take out your phone, let your date know that it will just be a second.

3

Ask your date open-ended questions.

Going on a date is all about getting to know the other person. Come up with a few questions ahead of time so you can leave the date feeling like you know this person a little more. You could try asking:^{[3]
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- What’s your favorite subject in school?
- Have you read any good books lately?
- What’s something you wish you were better at?
- What do you like to do for fun?

4

Try not to talk about your past relationships.

Hearing about your ex-partner can be a little jarring. Besides, it might throw up a red flag to your date. If you can avoid it, try not to talk about your ex until you know your date a little better.^{[4]
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- If it comes up in conversation naturally, it’s fine to spend a few minutes talking about your past relationships. However, if that’s all you talk about, your date might think you’re not ready to move on yet.

5

Throw in a few compliments.

It’s always nice to hear good things about yourself. If you notice something that you really like about your date, let them know by giving them a compliment. Stick to one or two compliments throughout the date to avoid going overboard. Try something like:^{[5]
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- ”I love the way you laugh.”
- ”You’re really fun to hang out with.”
- ”It’s so easy to talk to you.”

6

Tell your date about yourself.

Asking a constant stream of questions turns your date into a job interview. Make sure you tell your date more about who you are, too, so they can get to know you.^{[6]
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- You can respond to something your date said with a little tidbit about you. For example, “Oh, you have a dog? That’s super cool, I have 2 cats at home and they love dogs.”
- Or, “Have you ever gone mountain biking before? I’ve never gone myself, but it looks fun!”

7

Keep the conversation light.

The goal is to learn more about each other, not to start an argument. Stick to fun, light topics that are easy to chat about, and stay away from politics and religion.^{[7]
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- These are important things to talk about, but you can save them for when you know your date a little better.
- If you notice that a topic has struck a nerve or made them feel uncomfortable, back off the topic, apologize, and talk about something else.

8

Open the door for your date.

Chivalry can be an effective way to impress your date. You don’t have to do these things (and don’t force them if it feels awkward), but adding a bit of chivalry can leave your date feeling charmed.^{[8]
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- Chivalry doesn’t necessarily mean you have to pay for the date. You can ask your date to split the bill with you, if you feel comfortable.
EXPERT TIP

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

Our Expert Agrees: When you're going on a date, be a gentleman. Be on time, open the door for the person you're dating, and pull out their chair. It can be difficult to do sometimes, but it's a charming way to set yourself apart from the rest of the guys out there.

9

Tell them about how much fun you had.

This helps end your date on a good note. After a few hours, you both might be getting tired. If you feel like the date is winding down, let them know how good it was to see them and that you enjoyed your time together.^{[9]
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- Say something like, “Thanks for meeting up with me, I had a really good time tonight.”
- Or, “This was so much fun! I really enjoyed talking to you.”
- Even if you don’t see yourself going out with this person again, it’s still polite to tell them that you had fun.

10

Ask for a follow-up date if it went well.

This really lets your date know that you had a good time. You can see if they’re free next week sometime, or let them know that you’ll text them to set something up. You don’t have to commit to anything, so don’t feel pressured to go on another date if you don’t want to.^{[10]
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- Say something like, “I had a really good time tonight. Wanna do this again sometime?”
- Or, “It was so nice to meet you. Are you doing anything next weekend?”
- If you don’t want to ask for another date, don’t ask for one. You can keep it ambiguous for now and then let them know later that you aren’t interested.

11

Give your date a hug if you both had a really good time.

This is optional, and it depends a lot on their body language. If you were both smiling and laughing throughout the night, it’s probably safe to lean in. If your date seems tired or ready to get home, stick with a handshake instead.^{[11]
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- If you really enjoyed your date, you might go in for a kiss. Try a hug first, and then see if they’re smiling afterwards. You can either lean in and go for it, or you can ask them directly if they want to kiss you.

12

Make sure your date gets home safely.

Even if your date didn’t go super well, it’s the gentlemanly thing to do. You can walk them to their car, call them an Uber, or see that they get on the bus.^{[12]
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- Make sure you respect your date’s wishes! If they tell you they’d like to walk to their car or bus stop on their own, don’t push it.

13

Call or text the person to set up another date.

There’s no specific time period you have to wait before calling your date again. If you had a really good time, you could even shoot them a text the next day to see when they’re free.^{[13]
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- If you don’t want to set up another date, honesty is always the best policy. Let your date know that you just weren’t feeling it so they aren’t left hanging.

Community Q&A

Question

What if she never texts back about another date? Does this mean that she doesn't like me?

wikiHow Staff Editor
Staff Answer
This answer was written by one of our trained team of researchers who validated it for accuracy and comprehensiveness.

wikiHow Staff Editor

Staff Answer

If you don't get a reply about another date, you can wait a few days and then send another text. If you still don't get a reply, unfortunately, your date probably isn't interested. Try to move on and find someone who will reply to you!
Question

If you like each other but you are too scared to tell each other how you feel, what do you do?

Community Answer

Take the initiative and tell them that you like them. The other person will be more willing to open up and explain their feelings if you do it first.
Question

What if she dating somebody already?

Community Answer

If you know they are already in a committed relationship, you need to wait until it's over before you can ask her out on a date. Otherwise, you can both hang out in a non-romantic atmosphere.