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LOL, it most certainly is his first rodeo, if it wasn't he'd be better at this.
The whole thing seems creepy & that your are trying way too nude.
See that’s the weirdest part. When we’re together (and we online together) he doesn’t drink. Like, maybe a beer but not every day. Not even every few days. Like MAYBE once a week. So I can’t make sense of it. If he was an alcoholic I could have more empathy for him but he only drinks like this when he’s out with his friends.
This is very toxic behavior and you’d be better off without her. You’re too young to be so invested in someone who continues to show you she doesn’t care about you at all. She probably got so drunk to disassociate from you in that moment. Not sure what your living situation is but my guess is that she is using you because “you’d do anything for her” and you take care of her. She’s an asshole. You deserve better.
He’s actually a homeowner
I’m sorry but why is the fact that a middle aged man owns a home impressive to you. Most 40 year old are homeowners. When you’re 40 years old you’ll probably own your own home. Is it coz at 21 you don’t know many people your own age who own their own homes so this seems like a flex. This just highlights your age gap immensely.
You’re not mature for your age so that you have shit in common with a middle aged man. Think why no one his age (aka women with 2 decades more of life experience want him or why he doesn’t want them)
She wants your approval for cheating. Dump her like that she can flirt as much as she wants.
You'll never be alone… he'll be with you. in your heart for the rest of your life. Then? in the next place? Whatever that is? he's waiting.
Stay strong.
She was paying more of the overall bills than you, and you made her sleep on the couch instead of sleeping on the couch yourself? Good lord. I hope she never speaks to you again.