How to Ask a Stranger Out Online

Co-authored by Maya Diamond, MA and Hannah Madden

Last Updated: May 26, 2022 References

In the age of the internet, it’s easier than ever to connect to people we don’t know. When you spot a cute stranger online, asking them out is a little different than asking someone out IRL. We’ve compiled some tips to help you (hopefully) get a date with the person of your dreams.

1

Fill out your profile with your interests and hobbies.

Represent yourself online like you would in real life. Since the person you’re asking out knows nothing about you, add some information to your profile that explains who you are and what you do.^{[1]
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Expert Source

Maya Diamond, MA
Relationship Coach
Expert Interview. 17 January 2019.} Put up some quality photos of yourself in different scenarios so you look fun and interesting, too!^{[2]
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Expert Source

Lisa Shield
Dating Coach
Expert Interview. 13 December 2018.}
- This goes for any online platform, whether it be an online dating profile or just one of your social media accounts. If your profile looks boring or doesn’t have anything on it, your potential date might not want to go out with you.
- It might also help to check out the other person’s profile before sending a message. That way, you have a little info on them before you start chatting.

2

Send a friendly message to break the ice.

Start out by just saying hello for a simple, genuine approach. You can even introduce yourself if you want, since you two are strangers. If you have mutual friends, mention that in your opening line. It’s important to establish some sort of rapport before diving into asking them on a date. Try something like:^{[3]
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- “Hey! I’m Kevin, nice to meet you (virtually).”
- “Hi Lucy! My name’s Alice. I think you know my friend James.”
- “Hey, how’s it going?”

3

Get a conversation going.

Ask them how their day is or what they do for work. You’ll have much better success if you talk to them for a few messages before jumping into a date idea. Plus, you can learn a little more about them to see if you two might be a good fit. Check out their profile to get some info, then ask them questions like:^{[4]
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Expert Source

Lisa Shield
Dating Coach
Expert Interview. 13 December 2018.}
- “How long have you been rock climbing?”
- “How’s your day so far?”
- “What do you get up to on the weekends?”

4

Give them a compliment.

Let them know you’re a nice person and that you like them. Throughout your conversation, feel free to throw one or two compliments in the mix.^{[5]
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Expert Source

Maya Diamond, MA
Relationship Coach
Expert Interview. 17 January 2019.} You could talk about their personality, their hobbies, or even their career path. Stay away from anything about their physical appearance, though, as that can be a little bit creepy.^{[6]
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- For instance, you might say, “I really like chatting with you! I feel like we could talk about anything.”
- Or, “It’s so awesome that you’re into snowboarding. All your videos look so professional.”

5

Ask for their number.

Take your conversation offline to ask them out. If you’ve been having a nice chat but you aren’t quite ready to pop the question yet, see if they want to exchange digits. After that, you can text them a little more before asking if they want to go on a date with you.^{[7]
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- Say something like, “You seem really cool. Here’s my number if you want to keep chatting.”
- Or, “I really enjoy talking to you. Do you want to exchange numbers?”

6

Suggest a date activity.

Have something in mind so they’re more likely to accept. If you’re ready to ask them out, think back on your past conversation to find an activity they might like. Then, suggest a specific day and activity for you two to do.^{[8]
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- For instance, maybe you two talked about how much you both love coffee. In that case, say something like, “I was thinking of checking out that new coffee shop downtown this weekend. Would you like to join me?”
- If you know they’re into hiking, you might ask, “I’ve never been out to the Multnomah Falls trail. Wanna show me the ropes next week?”

7

Ask them for a suggestion.

If you aren’t sure what they like to do on a date, try this. You can ask them what restaurants they like or where they like to get a coffee. When they give you a suggestion, tell them that it sounds nice and that you two should go.^{[9]
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Expert Source

Maya Diamond, MA
Relationship Coach
Expert Interview. 17 January 2019.}^{[10]
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- For example, you might say, “What’s your favorite place to grab a drink around here?” When they answer, say, “Wow, that sounds nice. Want to meet me there this weekend?”
- Or, you might say, “If I wanted to get Italian food, where would I go?” When they suggest a restaurant, say, “That sounds amazing. We should go there tomorrow night!”

8

See if they have any plans this weekend.

Ask indirectly for a more subtle approach. If you aren’t sure whether or not they like you or not, gauge their reaction by seeing if they have plans. If they aren’t, then you can ask if they want to hang out sometime. If they are busy, it could mean they’re not interested.^{[11]
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- Say something like, “Do you have any plans this weekend?” If they say no, try something like, “Cool! I was thinking about seeing a movie on Saturday. Want to join?”

9

Try a flirty challenge.

Use this technique if you two have been flirting a lot. Challenge your potential date to come up with a really awesome date idea. When they do, tell them that they win and you’d like to take them out on that date.^{[12]
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- Say something like: “I bet you can’t come up with a better date idea than me.” When they tell you their plan, say, “Wow, I take it back—you win. Let’s do that!”