Ok so I met an older woman in the bar at the weekend, she's 27 and I'm 23.My style is trying to come across as childlike cute and quirky, I like a lot of Tyler Durdens older techniques, and well I think she liked me because I was talking to her for a while and she wasnt in a rush to leave.

Long story short, I couldnt make out with her, but I got her number. My guess, was has had her fair share of bad guys messing her around and that's why I come across as different. For some reason I told her I've never had a girlfriend, and some other bullshit I probably shouldnt have said but oh well.

Problem is, I woke her up at night, with a cute txt message. She didnt respond. Next day I text her asking if she rememered the other night. She said yes, told me I woke her up.
It feels rather cold and awkward.
I don't know how to recoup.

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I'm a lover, not a fighter.

hey, so she is like 31 or what?
You 23 and her 27? For me it's just normal age difference.

So..

you woke me up
_what_? you leave you cellphone on at night?
OR: So your sleep is really light. didn't know.

if she then pushes it, someting like
"I misjudged you. Obviously it was not on purpose, and you make a big deal out of it?"

Just change your frame or mindset slightly. Nothing awkward here, and quite understandable if people wake up in the middle of the night they are not too happy about it. She could have turned her phone off, you could have choosen a better time. That' it.

Next again, just sell the "no girlfirend thing" differently on a second date. "I like no strings attached until I find the right girl (otherwise it's a waste of time)".

So have fun on a second date then

(and yes, English is not my first language, those are just hints...)