How do I ask this person out on a date?

Thursday | March 7, 2024

Love Letters Dating

How do I ask this person out on a date?

Calling all people who need advice about their love and relationship lives:

What’s been on your mind? Ask a question. It helps others who’ve been wondering the same thing.

Submit your anonymous letter here.

Hello LL,

I do not have much experience with long-term relationships, or even just dating in general (basically none). I haven’t been bothered about it enough to do much about it for various reasons.

I am old enough to have been in high school and college before the advent of smartphones and social media. I have downloaded some dating apps before, but never really got into making active profiles and using them much. Now to the main issue: there is someone I’m connected to online who I think might have 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 stalkery. Ask for an in-person intro? We have some mutual friends, but not people I really know well enough to ask for an introduction. Show up to some events or places they might be at 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 that could lead to meeting and maybe more?

Thanks – and let the commentariat commence.

– How to Reach Out?

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, obviously, but when you enjoy something they’ve posted, you can reach out and ask a question about it. 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.)

Again, that idea might be too much for you. If so, see Option 1.

Before you do anything, make sure your own 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

Readers? What would be your next move? Would you pursue this at all?

Dating Crush

Featured Comment

“Most normal people would be flattered to be asked out. Given that you have mutual connections, first find out if this person is single. If so, proceed as Mere described by commenting on something of mutual interest to see if they engage. If they do, keep the convo positive and ask them out when the time is right – something simple like coffee or a drink. Regardless of the outcome, this will be a good way to practice your dating skills.”

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