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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.

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  1. 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.

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  1. 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 😉.”
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4

Ask him questions.

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  1. 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]
    • “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?”
    • Reader Poll: We asked 232 wikiHow readers, and 59% agreed that bonding over a common interest is a great way to start a conversation with someone online. [Take Poll]
6

Make him laugh.

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  1. 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!”
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  1. 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? 😜.”
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9

Give him your support.

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  1. 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!”
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10

Reveal details about yourself slowly.

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  1. 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!”
13

Try to get together offline.

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  1. 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 TIP

    John Keegan

    Dating Coach
    John Keegan is a Dating Coach and motivational speaker based in New York City. With over 10 years of professional experience, he runs The Awakened Lifestyle, where he uses his expertise in dating, attraction, and social dynamics to help people find love. He teaches and holds dating workshops internationally, from Los Angeles to London and from Rio de Janeiro to Prague. His work has been featured in the New York Times, Humans of New York, and Men's Health.
    John Keegan
    Dating Coach

    In-person interactions are really the way to go. Online dating can definitely be a useful tool for connection, but in-person hangouts are key to building a successful relationship. Try to transition an online connection to a real date as soon as possible!

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Expert Q&A

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  • 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.
    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.
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