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It was going okay before dude started bragging about how he went out with a lady not too long before. He wasn't all that into her and he said she clearly wasn't into him, but he paid for dinner and guilted her into going home with him because he "might as well get something out of paying for her." Giant red flag at this point. I went to the bathroom, when I came back the bill was on the table. He claimed that the server had brought it as one bill, rather than separate, and pointed out that she'd drawn a heart around the total in red pen. He refused to let me pay for my portion.
The thing is, it's standard practice for servers to ask if the bill should be together or separate here, and I'd always been asked at that particular bar. Dude wasn't a local and clearly didn't know that. This guy told me about how he used "but I paid so now you owe me" to coerce a woman he knew wasn't interested into having sex with him, and then immediately tried the same bullshit on me. He had deliberately asked for a single bill while I was away from the table. I'm reasonably certain he's the one who drew the heart on the bill too.
Needless to say, it didn't work. He still tried to drag me off to catch the train in his direction with him and got real upset when I told him to fuck himself and bolted. I'm very glad it was an early date so it was still light out. This guy did not take kindly to being told no.
As a dude, I'm constantly gobsmacked by how many dudes are just the fucking worst when it comes to dating. Like, fellas, it really isn't that hard to avoid being a creep.
My current partner and I are planning on getting married in the next couple of years. He's wonderful. I don't see this relationship ending, but if it does my best friend and I plan on throwing darts at a map until we hit somewhere we both like. We'll get a place and become old punk grandmas together because neither of us wants to deal with dating ever again.
Congrats and best of luck with plan A, but kudos for having a killer plan B!