Ok, so I'm not actually going in chronological order. Some dates were much easier to remember because they stood out. It's the bad ones that stand out - the good ones that lead to relationships are boring to read and write about.
I've always used current photos ( < 1 year ) and dress how I do in those photos. Typically jeans, loafers, a jacket ( usually a hoody ).
I'd had a few dates that month - hey, it IS about dating so don't be judging me on that. A woman practically stalked me to get this date. She'd written me, mentioned similarities in our profiles, said she's looking for a relationship, etc. We chatting online, then on the phone.. for quite a while. This was really looking to be an amazing date... or so I thought...
She'd asked me to a restuarant in a town ( I'll mention neither ) that I'd never heard of - I knew the town, not the restaurant. I'm up for anything - at least for a first meet I am.. so I agreed without question.
On date night - Saturday if I remember - we were still chatting a bit in anticipation. I arrived in town, had to deal with parking, and went about trying to find the place.
I'd gotten there a little early. I like to be early to make sure I know where I am, to get bar stools if the place is busy, etc. I hung out at a bar down the street waiting for her. She texted she was here and I walked to meet her.
I saw her standing in from of the bar - she looked great... but... then I got "the look"... that cutting, cold look of disappointment.. and I was about 20 feet away and closing in on my doom.
I did reach out to make initial contact, she obliged. We talked cordially and noticed the live was long. We decided to go to another bar. Fine.. that's never a problem.
We chatted at the bar. I'd noticed there really wasn't any positive body language going on, and I realized this was going nowhere but I figured, "Hey, and hour is fine - she made the effort".
Our conversation mostly consisted of her - her not so great career, her friend's cars, boats, vacations, the things she was used to in her marriage, and, of course, what a complete cad her ex was.
Then... she gets up to go to the bathroom. As she walks by I compliment her coat. Remember, I'm wearing my trademark hoody with a really nice button down shirt and my old loafers. She reaches out with one finger, touches my hoody, and declares with the confidence and verosity of Janet Pelosi yelling at Donald Trump and said: "THAT... is a little boy's jacket".
This did not embarass me on any level. She simply revealed herself and what she wanted, which I already had an idea of. Many women on dating sites are, well, broke. She knew I was self employed, and wanted to travel. What she had not counted on is that I'm very comfortable in my own skin - I don't wear ties, or suits, and prefer life in a very unpretentious way.
She was looking for a free ride, a sugar daddy, a way out of whatever situation she was in. I was listening for her complete LACK of interest in what she did for a living, and that all of her stories related to the wealth of others... but never hers.
What I bring to the table: No kids, time to spend with someone, varied interests, all of my teeth, a bank account etc..
What SHE brought to the table: A nice coat.
Being the morbid soul that I am, I paid the bill, walked with her to her car but for some odd reason she found it necessary to walk arm in arm. She continued to talk, questioning her decisions internally, and me just wishing we got to the car so I could go see that band at the other bar..
We got to the car.. I gave her a temped kiss on the cheek.. and then, just to see how she'd handle it, asked her if she wanted to meet again. She did say no, but I never assume - you'd be surprised what some women will do to achieve an indirect agenda... besides, she was cute. Of course she said "no" and that she wanted someone more "along" in their life. I read this to mean someone who wears ties and suits and likes pretentious restaurants and is looking for arm candy... which is not me.
Then it gets even funnier. I had already deleted her texts and phone number before getting 20 feet away. Can anyone say "NEXT!" :) I get a text from her about an hour later. Not just any text but a multiparagrah text explaining how I was not what she was looking for, etc.. I thought that was already established but she did feel compelled. I just deleted it.
The moral of this story is a simple one: She's not exceptional in online dating - there are lots of women who find themselves divorced from successul men when they're in their 40s or 50s without any visible means of support. They agressively try to hide that fact, and I'm begging to believe that they believe this behavior is OK. If looks and a nice coat were what I was looking for I'd get a younger, hotter model - not someone nearing the age of social security.
prologue: I've been asked back to that restaurant several times. Now that I know what it is, I use is as a filter for who I won't date.