max3732 Posted June 1, 2020 Posted June 1, 2020 One of my female high school classmates that is one of the few I kind of kept in touch with is in one of the pictures of someone I just found on a dating site. What's funny is just before graduation I had a crush on the friend in the picture and we started talking a little bit. She's married now and I haven't really kept in touch with her other than that I added her on Facebook/Instagram even though I don't really use them. The woman I matched with doesn't have much on her profile, but she has I really like. She has a lot of the major interests and she's in the same demographic as what I'd like to find. Plus she's cute! She only has a handful of pictures so it shocked me to see her with my high school classmates in one of them. She doesn't have any pictures of her with anyone else. How should I approach this? Should I message the friend on the picture and ask her about her friend from the OLD site? I messaged her about a year ago or so and we had a little conversation. Should I comment on the picture with my high school classmate and say something like "How do you know X? I went to high school with her!" Maybe a "clickbait" type message saying "Do you know what I found that's really interesting in one of your pictures" Or do I just ignore it and send her a message about one of our shared interests? My mind is kind of racing all over the place.
Erik30 Posted June 1, 2020 Posted June 1, 2020 51 minutes ago, max3732 said: How do you know X? I went to high school with her!" I think that's fine to open with. It's a nice coincidence, but it won't matter if she isn't interested... so there's no point in thinking too much about your first message. 1
smackie9 Posted June 2, 2020 Posted June 2, 2020 (edited) Just say hi....if you are hot looking she isn't going to care what you say....if you are not good looking, she's not going to care what you say. Approach it anyway you want and roll the dice. How you message doesn't become too much of a contributing factor how this will play out. Edited June 2, 2020 by smackie9
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