Search Results: approaching younger women

I approached a coworker & Asked her age.

She has a very Serious / mature demeanor, like a strict parent who’ll ground you.
Her hair is black, with Gray highlights.
She seems older, but looks my age in the Face.

I asked how old she was
& I kinda looked her up and down, I wasn’t checking her out, She’s attractive but I wasn’t.
I understand how it may have seemed like I was.

She started smiling & said it was a weird question, I explained how she looked young but the Gray hair was throwing me off.
She said ‘a woman never tells’

& She thanked me for noticing her hair..

Did I just unintentionally flirt with this woman?

I guessed her age, I said 24
She wouldn’t respond but she told me I was ‘pretty close’

I had this happen a few times when I was younger. I refrained to hit it fast because I saw her as a girlfriend potential and wanted something long term (there was definitely making out involved).

On three different occasions this approach ended the worst way possible for me (permanent friendzone). Lots of hope, heart, effort, time, money and worst of all my self esteem / reputation was completely really damaged. .

But seriously at what point do you risk her assuming your okay with being just a platonic friend

This doesn’t apply of course if she legitimately wants to wait to marriage. But if she says that then she better have very low number or be a virgin. High number women in this scenario are completely bullshitting you. Especially if they just recently slept was someone else before they met you.

Also, what's your approach to shy guys you fancy?

So I'm on the dating apps, looking for a long term relationship, mother of my children, wife material etc. I've found most women list confidence as a quality they desire. When I was younger, I used to be quite shy around girls, but some of them found this adorable, and I started to attract girls who are more assertive. But when looking for a partner, could this be an attractive quality?