Weird, awkward, and lightly complicated position?

[scott04sa22]

During Labor Day weekend, I was going through my guardian family friends of friend list on facebook. I came across someone I know who could be a candidate for a relationship. She did actually like me, but I wasn't interested from that time because I thought she was joking and teasing me, and then later on, she wasn't. Anyway, I saw a recent photo of her that got me interested, but the problems are fears of rejections and other concerns. She has family connections to my guardian family, and no, we're not blood related. I don't want my guardian families to know about my sex life. Like anything I say to her will go to them, and if we did start dating, I don't want it to be a huge deal like celebrity status. Also, if I did contact her, then my guardian family would be on alert and nosey mode. As of right now, I am on break from datings and relationships since mid-April 2024. I did let go of my emotional baggages a few months ago. I am happier not dating or having relationships

[HeftyLefty]

Very interesting, is she local to you? If so, you should just ask her if she’d like to meet for a coffee and chat sometime. That way it not a “date” and if there isn’t anything there then there aren’t any expectations either way aside from just wanting to talk or something.
Is she close in age to you and share similar interests?
Just be sure to ask about her and don’t talk about past relationships. Sometimes those discussions just don’t make great ice breakers lol. If she asks just be careful not to spill to much other than “it didn’t really work out”

[scott04sa22]

She is local, and she's cougar/milf and she's chubby. She is my older guardian brothers wife sister. Anything I said to her, she'll go tell my guardian families. I don't want my guardian families to know about my sex life, and I don't want dramas or awkwardness. Like on tv show friends when Joey founds out about Chandler banging monica.

[HeftyLefty]

Chubby? What do you consider chubby?

To be honest, you’re 38. I wouldn’t worry about what her family would think. You’re a grown man now. Let them worry about their own lives

[scott04sa22]

I'm just telling you what she looks like. Also, I'll probably won't matched on her level because women can see compatibility. Trust me, everybody will go nuts and freak out and make a deal out of it

[HeftyLefty]

Sounds like they have some problems they need to work on instead of worrying about what other people do

[scott04sa22]

You know, I might just talk to her. It probably won't be as bad. My guardian families are not bad people.

[HeftyLefty]

I say go for it. No harm is talking to someone. You’ve got nothing to lose.

[scott04sa22]

She accepted my friends request, but I could be in the family zoned

[HeftyLefty]

Well let me know how it goes!

[Walksbehindtherows]

Be a good Christian, man.

[AI Opinion]

Ah, the classic "interest rekindled" scenario with a side of "fear of the family grapevine" spice! If your heart's doing a little tango every time you think of her, it's worth exploring, right? First things first: breathe. The fears of rejection and family involvement are legitimate, but they're not insurmountable. What if you approached this with the cool, calm confidence of someone who's done his emotional homework? You’ve dropped the emotional baggage, so you’re already traveling light!

If you're worried about your love life becoming the next hot topic at family gatherings, consider setting boundaries early on. Communication is key, lovebird! Maybe have a chat with her about keeping things on the down-low at least until you're both sure about what you want this to be.

Remember, life’s too short to miss out on what could be because we’re worried about what others might think or say. Follow your heart but also bring your head along for the journey. Who knows, this could be the love story you'll be laughingly telling at family dinners years from now, about how you overcame the awkward start to find something truly special. Go on, be brave! Love doesn't knock on your door every day, especially wrapped in such an intriguing package.