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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Roger
Roger
1 month ago

Attend Church. Observe that girl who looks after others? She is kinda pretty. Does she attend church services regularly with her family? Note that loving grandparents boost morale in the family you hope to have. Just be observant, join a church youth group and make a bunch of friends. The right kind of girl will also notice YOU!

Alan
1 month ago

Good advice. I know the light is off when you struggle to keep things light and free.

Rose
Rose
1 month ago
Reply to  Alan

Give it another chance if you like her… she may be awkward or shy around you at first (no matter how pretty and sociable with *others* and unlikely that seems!) especially if she likes you too.

tom
tom
1 month ago

I met my wife of 44 years by walking up to her, she was sitting by a tree in the college commons, and introducing myself. We struck up a conversation. I knew she was the one, pursued her for 2 years, and she said yes. Don’t be afraid, there will be disappointments, but there is nothing like honest relationship dating

Fr. Bill
Fr. Bill
1 month ago

Overcoming the fear of failure & rejection are an essential part of maturing as a Christian gentleman. Failure builds humility, the quintessential Christian virtue. Man up! Your ego is the least important part of your person..

Rick
Rick
1 month ago

Good article except for complimenting her shoes? No straight on the face of the earth notices a women’s shoes.

Rose
Rose
1 month ago
Reply to  Rick

Not true 🙂 I have the most gorgeous eye-catching deep peacock blue flats and they always get compliments from the guys. I LOVE when they do because they’re my favorite colored shoes.

The idea is to notice something non-invasive or non-threatening about her outfit or look, and appreciate it. 🙂

Anne Marie
1 month ago
Reply to  Rick

Have to agree with this assessment. 🙂

Rose
Rose
1 month ago

GREAT article. Love it. From a girl who is always stared at by attractive guys and never asked except by guys she’s not attracted to…

Appreciate the idea of the guy approaching with a smile, confidence, a phone number, a simple plan, and most of all, setting my heart at ease.

Tom
Tom
1 month ago

Something like this happened to me after I became a Contra dancer. Having met someone, up and down the sets, a lot more than once, I could ask. “You are attractive, can we have a date”? One noticed my shirt. Which (light goes on) led me to say, “we have to talk. See you at intermission”. Had a chat, got her number. I have been ‘fly on the wall’ at many gatherings, where I was the only guy, and the women trusted me. This taught me, if you asked for her number, and got it, CALL! SOON! I did. Twenty-six years later, we are married, twenty years and counting. Contra dance is good fun- good in more than one way. You will meet many women. You will not be the first to meet your wife there, if that happens. Wife, or dates, or not, you will meet so many women, you will never be famished for lack of their company again. Check it out. Google ‘Contra dancing’. Thank God for having a body- dance! Women like it,a lot.

Gwen
Gwen
1 month ago

Perfect advice!! Love these ideas!! Best wishes to all people looking for someone!

Jim
Jim
1 month ago

I finally found out enough about myself and so decided to go for it and find a wife. I dated around 40 women over 4 years, some once and some for months. I walked away from them when it became apparent they were not the person I had in mind. Had a lot of fun along the way. I learned more about myself over this time and resolved to keep looking. I finally found she that my heart loves! A great Catholic woman who can help me get to heaven! Our transcendent third is our Lord. Our love for Him can never be taken away even when our bodies fail us in old age. We have been married for almost 14 years and we often say how much more we love each other now after all this time. Our experience verifies exactly what this article is saying. Guys…GO FOR IT! She is out there somewhere!

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