My question is about meeting people in non romantic, real life circumstances. As you can probably tell, I’m not exactly sure how best to phrase it, so I’ll give you an example.

I’ve been house hunting and going to a lot of open houses recently. Last weekend I saw a place that was listed by a really funny, attractive agent about my age. She has a decent social media presence and a friend liked her page, which is how the listing ended up as a suggestion in my feed.

Obviously, female realtors aren’t looking to be hit on while they’re trying to do their job at an open house, so our conversation was focused on my search and the listing. She mentioned having recently bought a place herself, and that she understood the challenges of buying as a younger, single person.

We exchanged info for professional purposes but I really enjoyed our talk. That got me to thinking about how common it is to meet people like this but to either never connect the dots or to be unsure how to pursue anything in a way that isn’t stereotypically creepy and disrespectful.

What say you, Reddit? Is there a good way to make something of these happenstance interactions or are these situations destined to end up as missed connections of sorts?

8 comments
  1. It’ll be creepy now. She sees you as a prospective client. Shoulda just went for it right away, stop playing games.
    Go for it anyway. Its only creepy if she doesn’t feel the same way. Then move on

  2. In situations like this, if you’ve got nothing to lose, what’s the problem with seeing if there’s anything more?

    I once asked a guy out who I saw regularly at a shop I went into. We’d always have a chat and a bit banter.
    I asked him (with some courage) if he’d like to go out sometime. He said he was flattered but had just started seeing someone new.

    Not the result I hoped for but I acted on it and didn’t just wonder!
    And I only went to the shop a couple more times after that. To be fair it was a vape store and I had quit.
    I had nothing to lose by asking him. I’m still pleased I did.

  3. I just started dating a guy who was the closing attorney for my house. He waited until after our professional relationship was over and then texted me to see if he could take me out for a drink to welcome me to the area. You could always do something like that.

  4. Once you’ve bought your house and won’t be speaking to her about that anymore then why don’t you ask her out. If she says no you never have to see her again, if she says no and you’re still in the middle of sorting out your house it could be awkward.

  5. Important context: she isn’t my realtor, just the listing agent on the house that was open. Also, that house wasn’t the one, but there’s a chance she reaches out about other new listings she gets in the future. It was truly a fleeting interaction of 25 minutes or so. With this question, I’m thinking about those people you meet in passing or non romantic contexts who surprise you and have you thinking about them after the interaction is over and it’s not easy to connect with them organically again.

  6. I think the whole thing about avoiding asking someone out while they’re on the job is probably a good rule of thumb. I don’t think it’s always a no-no, but in most cases it is.

    I get that you told us about above woman as an example, and maybe this isn’t the only particular instance you ran into like this.

    I guess I would say read the room. Do you really think said woman might be interested in you, or is she just trying to do the best she can at her job?

  7. Complete your business with them first if you have any, then at the end simply ask if they would like to get to get a coffee or dinner to get to know each other better.

    Dating in real life means making opportunity of happenstance interactions, and question is how to do it in a way that is appropriate for the situation. Short of a very few relationships like therapist and patient, there is always a way to do it.

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