10 Ways to Win a Girl Over (With Expert Advice)

Plus, awesome first-date ideas to strengthen your bond

Co-authored by Connell Barrett and Bertha Isabel Crombet, PhD

Last Updated: September 23, 2025 Fact Checked

If there’s a girl you’re crushing on, you might be wondering how you can win her heart. Maybe you’ve given it your best effort with little success, and you’re starting to worry that she’ll be the one who got away. Keep reading to learn all the best ways you can win your crush's affections. With these tips and tricks, along with expert advice from dating coaches Connell Barrett and Courtney Quinlan, you’ll be smooching up a storm in no time!

How to Win Your Crush's Heart

According to dating coach Connell Barrett, be clear with your romantic intentions without being too direct. Make her laugh and ask questions to really get to know her. Pay her sincere compliments and make her feel special.

1

Start conversations with her.

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Most girls are attracted to confidence. Just walk up to her and start a simple conversation. She'll get the hint that you are interested in her. Start with a simple conversation starter:^{[1]
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- "That's a really nice dress. Where is it from?"
- "I'm sorry, I'm new here. Can you show me where the library is?"
Meet the wikiHow Experts

Connell Barrett is a dating coach with over five years of experience helping singles connect by unlocking their best, true, most confident selves.

Courtney Quinlan is a matchmaker and dating coach with over 15 years of experience specializing in finding individuals a compatible partner.

2

Show interest in who she is.

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Ask her about her day and listen attentively. It's a simple way to show her that you are interested in what she does. When she starts to talk, give her your full attention and look her in the eye. Most importantly, don't interrupt. Ask her questions to show her that you were listening, and offer your opinion if you have one.
- For example, ask her how her math test went. If she got a perfect score, give her a high five! If not, ask her if there is anything you can do to make her feel better.

3

Make her laugh.

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Most girls say a sense of humor as an extremely important trait. Making her laugh begins with first understanding what she finds funny, and then adapting to her unique brand of comedy so that you can tailor your jokes around her specific sense of humor.^{[2]
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- For example, maybe she likes dry, deadpan humor or full-on slapstick comedy. You can try telling her dad jokes, making clever puns, or creating an entire language out of inside jokes based on your favorite movies, shows, or silly interactions in everyday life.
  - “What do you call fake spaghetti? An impasta!”
  - “Why don’t scientists trust atoms? Because they make up everything!”
  - “Why do you think the scarecrow won an award? Because he was outstanding in his field!”

4

Compliment her.

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A sincere compliment can brighten her whole day. Take time to reflect on what you like about her, summon up the courage to tell her, and be sincere. It’s also important to realize that a little compliment goes a long way. Complimenting her personality is a good instinct to follow, but if you want to compliment her looks, stick to her smile, hair, eyes, and style.
- For example: "I like how the color of your eyes matches your dress. Does one of your parents also have blue eyes?" or "I love your freckles. They really highlight your beauty."
- Reinforce how she views herself. If she thinks of herself as an athlete, reinforce her competitive spirit or athletic skills. If she thinks of herself as a thinker, praise her smarts. For instance: "Maybe you get this a lot, but I love the way your mind works."

5

Remember the little things about her.

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Learn what her favorite movie candy is and bring it over during your next movie night. It’s also important that you remember little things about who she is as a person, like her birthday, her eye color, and the names of her siblings. Remembering these things about her, no matter how silly they may be, shows her that you’re putting in effort and make your bond even tighter.

6

Flirt with her.

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A little flirting can take your bond to the next level. Barrett says to flirt based on the “green lights” she gives you, especially when it comes to touch.^{[3]
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Expert Source

Connell Barrett
Dating Coach

Expert Interview} "I call it the stair step system,” Barrett continues. “You start with small moves and if those small moves are met with green lights, then [proceed.] For example, if she reciprocates that first hug when she walks into the bar on the first date— that would be a little step.”^{[4]
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Expert Source

Connell Barrett
Dating Coach

Expert Interview}
- Break the touch barrier. Touch her hand lightly when you make a point or tell the kicker to a joke; rub her back quickly when you're reassuring her about something; touch the top of her shoulder when you want to get her attention.
- Playfully tease her. Preferably, tease her about something that she's confident about or good at. If she's great at school, for example, say something like "I wouldn't want to be on a science project with you, because that means I'd be pulling all the slack."

7

Don't play games.

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Playing games communicates that you don't care about her feelings. Believe it or not, some guys try to play hard to get with women. And most of the time, it fails because the girl misinterprets his distance for coldness. It's a waste of time and gets a relationship headed in the wrong direction.
- Quinlan says, “Don't play the ‘I'm going to wait 2 hours to text her back.’” She advises that you let your communication “be natural, and at the same time, don't smother her.”^{[5]
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  Courtney Quinlan
  Matchmaker & Dating Coach
  
  Expert Interview}

8

Be reliable.

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Most girls want someone they can count on. If you say you're going to do something, do it. If you talk the talk, be prepared to walk the walk. Girls (and guys, for that matter) hate it when people say they'll do something but never follow through. Don't be that guy. And even when she is having a good day, let her know you're interested in how she's doing.
- Have good friends who are willing to vouch for you when you need it.
- Be somebody who is generally well-liked, respected, and admired.

9

Be vulnerable and forthcoming.

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Be willing to share personal things about yourself. You've probably asked a lot of questions about her, but maybe she doesn't know all that much about you. Share interesting things that you're thinking, or stories about people you've come across. Share the parts of yourself that you're comfortable sharing, and maybe even the parts of yourself you're still scared to reveal.
- Put yourself in her shoes. What does she like talking about? How does she respond to criticism? What makes her different from other girls? What does she pride herself on? Answer these questions from her perspective and plan accordingly.

10

Ask her out on a date if you haven't already.

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Take your friendship to the next level by asking her out. Barrett says, “You just want to be clear and say, 'Hey, are you free for drinks on Thursday night?’”^{[6]
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Expert Source

Connell Barrett
Dating Coach

Expert Interview} You don't even have to say it's a date if you think that will feel awkward. Just say something like: "Hey, so I got two tickets to that new movie on Saturday, and my friend bailed. Would you want to go?"
- Go on an exciting date, do something that raises her heart rate, like a haunted house, or a theme park with roller coasters, or a horror movie. Dates that are exciting have a better chance of promoting a bond between you two because you feel like you've been through something together.^{[7]
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- Be a gentleman. Open doors for her, be on time, pay for the date, and don't expect a kiss on the first date. Move at her pace and make her feel comfortable. If you make her feel comfortable at every step, she should melt into your arms.
  - Quinlan says, “Chivalry is definitely not dead. So, be chivalrous from the get-go. Open doors, pull out chairs, flirt with her. Get her chocolate if she likes chocolate, or her favorite kind of desserts.” Sounds like sweet and wise advice!^{[8]
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    Expert Source
    
    Courtney Quinlan
    Matchmaker & Dating Coach
    
    Expert Interview}
EXPERT TIP

Connell Barrett
Dating Coach
Connell Barrett is a Relationship Expert and the Founder and Executive Coach of Dating Transformation in New York City. Connell has over five years of experience as an international coach who helps men connect with women by unlocking their best, true, most confident selves. He is the author of the Amazon bestseller “Dating Sucks but You Don’t,” and has appeared on Good Morning America, the "Today" show, Access Hollywood, and in Best Life, Cosmopolitan, and The Oprah Magazine. In 2019 he was named Datezie.com's “New York City’s Best Male Dating Coach."

Connell Barrett
Dating Coach

Make sure she's ready before you try to kiss her. One common dating mistake that men make is what I call the lunge. They're chatting with a woman or they're on a date, and he's afraid to make a move, so he barely flirts with her. Then, at the end of the night, he lunges in for a kiss abruptly, and it ends up being very awkward.

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Tips

Respect her above all else, even when you’re in conflict.

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Don't be overeager. Let her come to you once in a while.

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Come up with a sweet or funny pet name for her and use it when it’s appropriate, to either lighten the mood or make her laugh.

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