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Is it possible to approach someone you’re connected to online without creeping them out?

If the connection isn’t on a dating website, Meredith sees some possibilities for reaching out.

Love Letters

Q. I do not have much experience with long-term relationships, or dating. I haven’t been bothered enough to do much about it. I am old enough to have been in high school and college before smartphones and social media. I have downloaded some dating apps, but never got into making active profiles.

Now to the main issue: There is someone I’m connected to online, and I think there might be great potential for a relationship. But I don’t really know them and am stuck about how to reach out further. “Oh, I’ve looked through your profile and posts, and we seem to match up on interests and values”? Seems kinda stalker-ish. Ask for an in-person intro? We have some mutual friends, but not people I know well enough to ask. Show up to some events or places they might be and hope to meet in person? Sorta sketchy.


They seem to maybe be single and looking, but it’s not clear.

Any good ideas/suggestions for non-weird ways to reach out? Thanks.

– How to Reach Out?

A. I assume your online connection is not through a dating app — that you found this person through Instagram or something like it.

With that in mind, I see two ways to do this. One is to send a message about one of their posts, to see if they’ll engage in conversation. As in, “I’ve always wanted to try that restaurant. Any dish you loved?” Or “That electric bike is so cool! I’m in the market for one. . . . Where did you get it?”

I’m inventing scenarios and images here, but when you enjoy something they’ve posted, you can reach out and ask a question. If it turns into a conversation, you can move to the next step.

The second option, which is much bolder, is to ask them to get coffee. That might be too bold for you (and me . . . and them . . . ), but if they’re looking to date, they might enjoy being asked out. You could start by saying who you know in common. As in, “We both know Beth, and I love everything you post. Want to grab coffee? No pressure, but I’ve been trying to meet cool people in real life, as opposed to just nodding and smiling at their social media.” (You can come up with words that better match your personality.)


Before you do anything, make sure your profile is what you want this person to see. I’m sure their first move will be to figure out who you are and what you’re all about.

Also, take a beat to consider whether these mutual friends could be helpful. Sometimes I get texts from people I haven’t seen in five years that say, “Hey, I just matched with a guy online, and the internet says you know him. What can you tell me?” I’m always happy to help. Maybe these mutual acquaintances can guide you.

– Meredith


Most normal people would be flattered to be asked out. . . . Regardless of the outcome, this will be a good way to practice your dating skills. PENSEUSE

I vote to show up to some sort of public event and establish contact that way. It’s the least likely to put one-on-one pressure on you. LUPELOVE