theres an older woman on my block who keeps saying hello to me in that sultry suggestive way she even winked at me once while smiling

how do I escalate things with her, realistically without looking like a massive desperate sperge

I dont get any attention from women otherwise even though Im not too bad looking, but I am on the heavier side

>shes just being nice
normally Id agree except for the time she winked, I dont see how you interpret a wink in this day and age as anything other than sexual interest. also she plays with her hair a lot when she says hello

pic unrelated

First of all, what do you want from her? have fun or projecting yourself in a serious relationship? if it's the last thing, don't do it. In short, there are many complexities in dating older women and expecting that one of them would become your wife, specially if she has already her own children

Anyway, your best bet, I think, is to just approach to her casually, saying something like: "Hey, we've been seeing each other quite a lot, and we didn't know our names. So what's your name?". Then at the end of the conversation ask for her number. Don't text her immediately, in fact, wait until night or the next day to do it

Then it's on your hands, Anon

>>81752861
and we don't even know our names*
Please forgive me, I'm feeling sleepy already

Lucky bastard.
Say to her that she should have you over for a drink sometime.
On the surface innocuous, but very obviously a chance for her to fuck your brains out.
>TFW no access to MILF sex in my block.