How to ask her out: The art of the date

By Ava Ladky

Published on August 3, 2025

Ever wondered how to ask her out?

Ever wondered how he should ask me out?

You’re not alone.

On the way to a volleyball game, my friends and I were all chatting about our weekends. One of the guys, a university student in his early twenties, mentioned a dressy event he’d attended. 

“Kinda sad not having a date,” he said, his thinly veiled disappointment turned into a light-hearted joke.

“Did you ask anybody out?” I asked. 

He looked me right in the eyes and answered sheepishly, “No.”

Tejas Kotha / Unsplash

How to go on a date 

Ask. Literally, ask. The girls are begging you. 

Strike up a conversation to build your confidence. See if this person you’re attracted to is the type of person you want to spend time with. 

If you keep practicing this skill, rejection will also get easier. Ever heard of rotational dating?

Keep the conversation warm, genuine, and direct. The worst thing that can happen is she says no. You’ll be no worse off than you are right now. Be okay with walking away with your head held high after rejection. You’ll never know if you don’t try. 

It helps if you have an event or activity in mind. I’ve been on dates to museums, the park, kayaking, and even rock climbing! You can still impress your date without a bouquet of roses and a candlelit dinner.

Yes, the sky’s the limit, but all you need to do is invite her to join you in something you enjoy. It’ll keep you both entertained and engaged without putting so much pressure on the “first date.”

By choosing an activity ahead of time, even if it’s “grabbing coffee or dinner sometime” your date sees your personality and interests. Clarity builds confidence. You also have the advantage because you’re doing something in your comfort zone. 

  1. Strike up conversation. Keep it simple, look at your surroundings.
    1. Is there a game on television at the bar you could talk about? 
    2. Is she reading? Ask her about that book. 
    3. Compliment (respectfully) on her outfit, maybe her shoes. 
    4. In line at a bar or cafe? Ask for drink recommendations. 
  2. Introduce yourself. Smile! This is the genuine part. The more confident you are, the more interested she will be.  
  3. Invite her on the date and give her your number. This is where you’re being direct. A number is so much more attractive, honest, and assertive than a social media platform. It shows you’re a man who is serious about getting to know the person in front of you. 
Josh Withers / Unsplash

Pre-date

You have her number. She said yes. Now what? 

  1. Be able to pay for your date. If you’re grabbing coffee, make sure you can pay for hers, too. It’s a gesture that makes you masculine and ensures she feels taken care of. 
  2. Set a time and place. Confirm those details with her over text. 
  3. Show up on time at the said time and place.
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On the date 

Okay, you made it. Let’s make it memorable, fun, and keep your date coming back. 

  1. Ask her questions. Get curious, be observant, and ask some out-of-the-box questions, that’s usually where good conversation is, not in the everyday questions. This makes all the difference, trust me. You want to make your date feel special. When only one person is monologuing, it sucks the fun out of the exchange.
  2. Enjoy yourself and invite her into that. Sometimes, a date sucks. You feel alone, there are long lulls in conversation, you realize you are no longer interested, and that’s alright. If you are willing to have a great time, no matter the other person’s attitude or your own feelings, they’ll pick up on that. They will want to mirror that. Your enthusiasm for her and your surroundings is attractive, regardless of whether this date leads to something more.
  3. Be present. Put your phone away and engage. People remember how you make them feel more than what you say.   
  4. Mind your manners. Be kind to others and your date. Bonus points if you open doors and let her walk on the inside of the street!
Dominic Sansotta / Unsplash

Follow-up after the date 

Here’s what to say so you can end your date with clarity. 

If it went well, invite her out again and add a personal touch. 

  1. Tell her you had a great time with her and would like to see her again. Suggest another date idea for next time based on the shared conversation you had earlier.
  2. Text her within a few hours, saying how much you enjoyed spending time with her, and are looking forward to next time. 

If you’re not sure, let’s end the date with kindness and send a follow-up text.  

  1. “Thank you for tonight, it was nice getting to know you more.”
  2. For the follow-up text, thank her for the date without leading her on. Explain that you’d rather be friends if needed.

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