Dating : How do I approach initiating a casual/FWB relationship?

Dating : How do I approach initiating a casual/FWB relationship?

I [22M] recently left a rather emotionally taxing, long term relationship, deciding that I need to focus on myself more than anything. But now that Im newly single, I kind of want a ‘breath of fresh air’ of sorts and to try and initiate a casual, nothing serious kind of relationship or FWB.

A high school friend of mine recently came back into town and walked into my store the other day. She let me sit down with her on my lunch break and chatted away for a while, like not much time had past. We were pretty good friends in high school, we had several classes together, and led a couple of extracurricular clubs together, but it was never a bff goals kind of situation. After graduation, we left our town for college and kind of drifted apart. I always had a crush on her, and shes everything my last relationship wasnt; independent, strong willed, very outgoing, etc. She said we should hang out sometime, and Ive been thinking about asking her out for some drinks, and have kinda been wanting to try and slide into her DMs.

I have zero clue where to startor how to even bring it up without being weird, since the only kind of relationships Ive been in before have been serious. And I dont want to make things awkward between us, since even if nothing happens between us, Id still kinda like to rekindle our friendship. What can I do to hint at/ tell her what I want without coming off the wrong way?

And on a side note, is this a healthy sort of feeling I should be having? I want to sort out my own baggage and work thru my own problems, and I cant shake the feeling this is somehow wrong of me.

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What do you think?

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  1. You feel wrong because you still feel guilt over a broken relationship. It’s normal, especially if the breakup was recent-ish.

  2. You may want to work on yourself first and not start anything new. I know it’s difficult. But trying to do a FWB thing could get messy. Has she given you any indication that she is interested in that?

  3. I’ll give you some unethical advice on how to make this happen. Basically wine and dine her just like you would any girl you’re interested in. Do not by any means tell her that you want a FWB. She will ghost you. Give off a vibe that you’re interested but at the same time keep some distance. Don’t text her too much, don’t always be available. If she asks what kind of relationship you’re looking for be vague. by all means do not say you want a friends with benefits. Wine and dine her until you get laid, and after that show her enough interest to keep her coming back for more.

  4. You’re not wrong, but seriously and scientifically, women’s brains are not wired for NSA or FWB. They will fall every time.
    Unless she’s a sociopath.
    Women equate sex with love and if she orgasms with you, that’s like setting it in stone.

    You can feel her out, I would just ask her flat out instead of playing games, so that she knows your intentions going into it. That could help if she doesn’t have any expectations up front.

    Just understand that nature is working against you here.

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