How to Win a Man's Heart Online

Co-authored by Hardy Jean and Hunter Rising

Last Updated: October 4, 2022

Have you found the man of your dreams online, but aren’t sure how to make him see you as a potential partner? If you want to win the heart of your crush, having a great conversation online can make him fall for you even harder. Luckily, you can easily show off your best qualities and stand out from the crowd online. We’ve got everything you need to know about what to say and how to keep him interested so he falls for you.

1

Show off what you’re up to.

Showing him you have a life will make you seem more interesting. Guys want to be with someone that has their own hobbies, goals, and interests, so share what you’ve been up to on social media. Post exciting pictures of you having fun and doing your favorite things so you’re bound to stand out from the crowd. If you’re lucky, he might have a similar hobby that you can bond over.^{[1]
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- List a few of your hobbies in your dating profile so your crush has an idea of what you like to do.

2

Like and comment on his recent posts.

He’ll know you’re into him if you interact with him on social media. Look through what he’s shared in the past couple of weeks and like a couple of the posts. If you want to start a conversation with him, leave a comment asking for more details about the post. By showing him you’re genuinely curious about what he’s doing, he’ll be more likely to open up to you.
- If he posts a selfie of himself, say, “Looking great! What are you all dressed up for?”
- If he shares a post about a project he just finished, try, “Wow, this is incredible! How long did it take you to make this?”
- If he posts a link to a funny video, say, “LOL this was hilarious! How do you find stuff like this?”
- Like a variety of his posts instead of only interacting with attractive pics of him. He’ll like that you care about more than just his looks.

3

Slide into his DMs.

Start a private conversation so you can break the ice. If you don’t want everyone else to see what you’re saying to the guy you like, send him a private message on social media or on a dating app. Say more than “hi” or “hey” so he has something to respond to. You could ask how he is or mention something he posted recently.
- “Hi there! How’s your day going so far?”
- “Hi hi! I’m not sure if we’ve met IRL, but your posts are so inspiring! They make me smile every day 😊.”
- “Hey! I didn’t want to embarrass you in the comments, but you looked amazing in that pic 😉.”

4

Ask him questions.

Lighthearted questions show him that you want to learn more. Scan through your crush’s social media or dating profile to learn more about what he likes so you have a good jumping-off point for your conversation — looking for common ground is great way to really build familiarity with the guy, because it creates a semblance of safety, and people are typically more willing to open up to someone if they feel as if they share common passions, viewpoints, and other views. You can also ask about how his day was, what his hobbies are, or what his favorite memories are. Stick to open-ended questions that need a longer, more thoughtful answer so you get him talking more.^{[2]
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- “What inspired you to get into drawing?”
- “What’s your favorite memory from when you were a kid?”
- “What was your favorite TV show you watched growing up?”

5

Give him a compliment.

The guy you’re into will love hearing what you appreciate about him. You could comment on his pics or something that he said during your conversation. Try to make your compliment stand out by mentioning something unique you’ve noticed or following up with a question so you can keep the conversation moving.^{[3]
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- “That last pic of you is 🔥 How’d I get so lucky to be chatting with you?
- “OMG it’s so cool that you’re into board games. What one is your favorite to play?”

6

Make him laugh.

Guys love it when you share the same sense of humor. If you know a good joke, pun, or funny story, don’t be afraid to drop it into your conversation. If you can make him laugh, he’ll want to talk to you more and spend time with you. Texting funny things early on is a great way to really break the ice before slowly building up into more emotional subjects.
- “It’s so cool that you like to go camping. I heard it gets pretty in-tents 😜.”
- “Ugh I wish I could go on vacation. Let me just pack my bags so you can pick me up 😉.”
- “Guess who just spilled their coffee on the way to work? Hahah if you said me, you’re right!”

7

Share something that reminds you of him.

He’ll love the idea that you’re thinking of him even when you aren’t chatting. If you scroll past a meme, picture, or anything interesting that makes you think of your man, forward it to him! Let him know that he was on your mind and what about it reminded you of him. It’ll be sure to put a smile on his face and make him think of you too.
- LOL I saw this meme and it immediately reminded me of our conversation earlier 😂.”
- “I really think you’d dig this song! It came on shuffle and it made me think of the playlist that you sent me.”
- “OMG I had to do a double-take because I saw someone who looked just like you! Are you sure you’re not at the mall? 😜.”

8

Flirt with him.

Tease that you like your crush to keep him on his toes. If your man hasn’t caught on yet, send him a few flirty messages to let him know that you’re interested. Be light and playful in your messages. He’ll really love how confident you are in your feelings and it may make him fall for you more.
- “It’s a shame you aren’t here right now. We could have a lot of fun 😉.”
- “I had a dream about you last night 😏 can you guess what it was about?”
- “It feels a little lonely over here. Do you wanna come cheer me up?”

9

Give him your support.

Be there for him when he needs it to show your crush he can trust you. Guys want someone that will cheer them on. If he’s really invested in a hobby or project, tell him how much you appreciate the work he’s put in so it doesn’t go unnoticed. If he’s going through a rough patch, send him a few words of encouragement and boost his confidence to let him know that you’re rooting for him.
- “You’ve done a ton of amazing work! I’m so proud of you for finishing your project!”
- “I know that it’s been a tough day, but I know you’ve got this! I’m always here if you need to chat!”
- “That video you made looked awesome! I can’t wait to see what you come up with next!”

10

Reveal details about yourself slowly.

Stay a little mysterious so the guy you like has to chase after you. If you tell your crush everything about yourself right away, he won’t have anything else to learn about you. As you’re talking about yourself, end your messages on a cliffhanger so he has to ask you more questions to keep the conversation going. As he keeps asking for more and showing his interest in you, tell him more details until he has the full picture.
- “That reminds me of something that happened to me when I was younger. You’re gonna LOL when I tell you!”
- “You won’t believe how embarrassed I was, but that’s a story for another time 😉.”
- “I’m so excited for my birthday! I bet you can’t guess when it is!”

11

Talk about positive topics.

The guy you like will have a lot more fun talking about lighthearted topics. If you’re always complaining about something every time you chat with your crush, it might put you both in a negative mood. You want to show the guy you’re into how much fun he’ll have when he’s with you, so keep your conversation upbeat. Talk about the things you enjoy doing and add a couple of emojis to your texts to help lighten the mood.^{[4]
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12

Make time to talk to him.

Reply to his messages to show him you want to build your connection. While the guy you like shouldn’t be the center of your attention, you should still show him respect when he reaches out to you. You don’t have to stop what you’re doing to message him back, but make sure you send a thoughtful reply within a few hours of receiving his message. That way, he’ll know that you’re still interested and not trying to play games with his head.^{[5]
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13

Try to get together offline.

He’ll see that you’re really serious if you want to spend time with him. While you’ve probably built a good connection online, you can test out your physical chemistry when you see each other in person. Suggest getting together for a coffee or going out on a romantic date so you can bond even more. Your confidence will impress your crush and make him fall for you even more.
- “I’ve really loved getting to know you here! Would you like to grab dinner with me this Saturday?”
- “We should try to see each other soon! When are you free this week to chat over a coffee?”
- “I’m so excited to hang out! You and me, bowling next Tuesday night? 😊”

Expert Q&A

Question

What can a man do to win a woman's heart online?

Hardy Jean
Dating Coach
Hardy "Coach DT" Jean is a Dating Coach and the Head Coach & Co-Founder of Way Tooo Spicy LLP, a relationship and dating coaching service based in Boston, Massachusetts. Hardy's specialties include trauma healing, self-love practices, and modern dating tactics in an increasingly virtual world. He works with his clients to upgrade their dating experiences through healing trauma, implementing uniquely personalized dating gameplans, and empowering clients to attract partners that they deserve. He has a BA in Legal Studies from the University of Massachusetts Amherst and is currently pursuing his Juris Doctor at Northeastern School of Law.

Hardy Jean

Dating Coach

Expert Answer

Be proud of your accomplishments and talents—women love men who can confidently talk about their achievements without coming off as being cocky. A big part of that is really just having a proper reference point for your competence; for instance, rather than talking about how great you are, talk about the impact an experience had on you. That way, you get to give a little more insight into who you are personality-wise and what values really resonate the most with who you are.