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1st time asking older woman on date
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1st time asking older woman on date

“ tbh it just felt awkward coz im your “ate” 😂🤣 i promised your mom that we’ll b here for you guys… as family. 😝 🥰 she’s probably laughing at us! 😇 but joking aside, let’s make it a friendly date for now in that way i wont feel awkward. ok?! 😜”

M32 asked out (my neighbor) woman in late 40’s/early 50’s. That was her reply when we texted about it after seeing each other in person. In person she was saying like okay but in a non-committal tone, for sure awkward or flustered or maybe thrown off vibe but didn’t wanna be rude about it. (Context, “ate” is like older sister in Tagalog/filipino but can be used w/ non related females, and I am not in anyway related to this woman. It’s more sign of respect and she was pretty cool with my mom before she passed away).

She was smiling about it and did seem flattered. Prolly thrown off for sure. She had ugly divorce and mentioned she always attracts the wrong kinda guy. Is there a chance here ? She does have personal/family issues. She’s in therapy, so am I. My first time asking out an older woman on a date, she did seem into it more than she wasn’t but based off her reply, any insight anyone? Presented it to her that I feel she genuinely doesn’t do anything for herself for enjoyment to tend to familial needs and I really just wanna take her out cuz she just doesn’t make that effort for herself and I think she deserves it. I did reply it can be whatever kinda date she wants it to be. I think I’m a genuinely attractive guy, like I’m not ugly, average body. We’re both nurses and Filipino. Her F22 daughter moved out maybe almost a year ago and they’ve had this strained relationship since I’ve known them the last 7 years. I live next door by myself. I’ve only ever seen her bring a man she was dating home once for a bit but 4-5 years ago. Since her daughter moved out, never see other cars let alone her walking in with a man.

Not sure if her history of breast cancer and reconstruction surgery has any play in this. We have had heart to heart talks about her daughter and other family things on her end and mine.

Kinda hoping the “for now” is a glimpse of she may be down to advance past just a friendly date at some point. I’m in doubts she’s ever been asked out by a younger guy. There’s times we texted and she’ll use flirty/winky face emojis too. So sometimes I felt she was kinda flirting with me then. She did reaffirm she wasn’t mad I asked her out or anything and that she was flattered and appreciated the gesture.

Any thoughts anyone ? I’d like to think she’s actually more into the idea than not. Like casual fun with a younger guy. I reassured her not trying to get us involved in any drama or problems, the date proposal is just for us to have some fun.

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Profile updated: 3 days ago
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3 months ago