How to Approach a Guy Online: 10+ Messages You Can Send to Get a Response

Co-authored by Christina Jay, NLP and Hannah Madden

Last Updated: July 5, 2024 Approved

Whether you’re online dating or you just spot someone cute on social media, approaching a guy online is a great way to get a conversation started. Picking the right opening line can be the difference between a fun chat and a message left on “seen,” so it’s important to pick the right one. Read through these options to strike up a convo with a guy online to see where it goes.

1

Talk about something on his profile.

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Personalize your message to catch his attention. Before you send your opening line, take a look at his profile and see what he likes. If you notice a ton of hiking pics, ask about the last trail he really enjoyed. If there’s a ton of food pics, get a recommendation on which restaurants are the best around town.^{[1]
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- For instance, you might say, “I see that you like to hike! Have you been to any fun ones this season?”
- Or, “So you’re a foodie, huh? Have you tried the new Mexican restaurant downtown yet?”
- Reader Poll: We asked 266 wikiHow readers how they initiate conversations with guys online, and 48% said they talk about something on his profile, like his photos, prompts, or bio. [Take Poll]

2

Give him a compliment.

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He'll love hearing something nice about himself. If you see something on his profile that you really like, send it in a message to catch his attention. You could compliment his looks, his hobbies, or his personality. For example:^{[2]
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- “You have such a nice smile!”
- “Wow, you look really strong. Do you work out?”

3

Ask for a new series recommendation.

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Start a conversation by asking for his opinion. Ask him to recommend a new TV show or movie that you can watch in your free time. You’ll get a sense of his taste in media and he’ll feel like you value his opinion. You could say:
- “Help! I need a new series to binge, stat!”
- “What’s the best movie you’ve watched in the past year?”

4

Try a “This or that?” question.

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Get a fun little game going with this question. Pick anything: food, animals, cities, celebrities, and ask him which one he prefers. It will be a nice way to show off your sense of humor so you two can get a bit of banter going. Try something like:^{[3]
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- “Pizza or burgers?”
- “Chicago or New York?”
- “Cats or dogs?”

5

Ask about a common interest you have.

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Check out his profile to see if you have anything in common. If you do, really lean into it so you have something fun to talk about. Remember to always be truthful, and don’t lie about a common interest you don’t have. You could say something like:^{[4]
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- “You went to Portland State too? I graduated from there last year!”
- “How weird, I just moved here from Alaska as well! Small world, isn’t it?”

6

Try a cheesy pickup line.

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Guys don’t get approached with pickup lines very often. You can make him giggle and start out on the right foot by using a ridiculous line (the cheesier the better). If he appreciates it, he might even send one back. Go for one like:^{[5]
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- “Why is someone as hot as you looking for a date?”
- “Did it hurt when you fell out of heaven?”
- “If I could rearrange the alphabet, I’d put U and I together.”

7

Ask a “would you rather” question.

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Start a conversation with a hypothetical scenario. Pick something a little ridiculous and ask the guy what he would choose. If you disagree, you can have a flirty debate about it as you continue the conversation.^{[6]
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- For instance, you might say, “Would you rather fight 10 duck-sized horses or 1 horse-sized duck?”
- Or, “Would you rather eat beans for every meal or have to drink 1 gallon of milk every day?”

8

Talk about an embarrassing moment.

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Ask him about his and then talk about yours. It will break the ice, and it’s a fun way to start a conversation. To make it a little less intense, ask about an embarrassing moment from his teen years.^{[7]
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- Say something like, “What was the most embarrassing thing that happened to you in high school?”

9

Break the ice with a gif.

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A funny one might catch his attention. Scroll through your gifs and pick one out that’s a little silly and kind of flirty. If it works, he’ll probably send a gif back to start out your conversation.^{[8]
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- For instance, try a gif that says “How you doin’?” or “Hey cutie” for a fun opening line.

10

Get deep with a personal question.

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Keep it light, but ask him a question that lets him talk about himself. If he’s a good conversationalist, he’ll ask you the same question so you two can get to know each other better. It will help you move past the small talk and into a deeper conversation.^{[9]
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- Try something like, “What makes you happy?”
- Or, “What’s your biggest fear?”

11

Tell him you’re about to flirt.

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Set yourself up for success with this bold line. If you think he’s really cute and you don’t want to beat around the bush, just come out and tell him he’s about to get flirted with. He’ll probably find it charming and sweet!
- Say something like, “Watch out, here comes a flirtatious message!”
- Or, “Please don’t judge me, but I’m about to flirt.”

12

Ask him out on a date.

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Skip the small talk and just go for it. If you aren’t a fan of DMing back and forth for days, let him know by asking him out. This works well on dating apps when you’re both there to find a potential romantic partner. You could say something like:^{[10]
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Expert Source

Christina Jay, NLP
Matchmaker & Certified Life Coach

Expert Interview. 11 February2020.}
- “So, when are we getting that drink?”
- “If you want to go on a FaceTime date, just send me your schedule.”
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 meet-ups are key to successful relationships. While online communication can be a useful tool for connection, relying on texts and DMs can hurt your ability to develop real-life communication skills. Try to quickly transition an online connection into a real date!