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Should I Pursue Her?
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Hey fellow friends,

I am a single male obviously, 32 years old. There is this girl that I have had my eye on for a long time. She is not the type that dates any person. She is extremely selective from what I can tell. I never met her in person officially but we have many close mutual friends in our town and have been to the same places. I have been friends with her via social media and conversed, DM, exchanged numbers, etc since I was in college which is now 10 years ago or so.

Both being in relationships and life happening in the past I remember asking and getting her number years ago but for whatever I never followed through at the time. Probably exercising many options and other interests. Now I find myself single at a time where I am looking for an elevated relationship and seeing her on my social media feed has reminded me that I always wanted to see if something can happen with us. She is not the woman you just take as a game, she is definitely is the wife material type and comes from a good family. I can tell she isn't the girl going around the block dating guys left and right simply by how she carries herself and the fact that she has had maybe 2 boyfriends in the entire time I've followed her. She is a very beautiful girl (European model type) so I can imagine how many have flocked to her DM.

Now, even when I was in my recent 2.5 year relationship I always felt her in the background. On Instagram, she is one of the first people to consistently look at my stories, likes my posts, etc. I'll reply to her story and she doesn't leave me on seen, she always replies or likes my message. I do believe she is old-school and believes the man should pursue which I completely understand. I know I should just give it a try because of the "you miss 100% of the shots you don't take" cliche but although I feel like she has given me some clues, I am human and realistic and are afraid of any rejection. Maybe I am totally off on her hints and those social media cues mean nothing lol.

Any tips or advice on what to do? and if so how should I ask her out?

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3 years ago