Upstart's Progress Log - Date with Russian MILF from Moscow

[Squilliam]

Uhh, restaurant (I didn't say dishwasher) . But only for a little while longer, soon I'll have my art career off and running, haha.

Oh, does your industry make a lot of money?
Not really, unless you're really good (like me) I had to resist the urge to pull out my instagram to prove myself.

I keep getting into this dynamic with older ladies it's like they have all the expectations I can't meet because I'm fucking broke.

I just have this discomfort around being so poor, I'm literally below the poverty line. I don't even know how I'm surviving off of negative money at the moment. Payment plans, and recurring bills I guess. Always teetering on the edge of financial ruin, again.

When she mentioned that for next date we should go on a glass bottom boat ride, I had a mini panic attack.
I can barely afford to EAT right now, betch!

EE women are generally pretty strong framed. My ex was EE (well, 2nd gen tho) and honestly it was a lot to handle. Those women typically have a very rigid standard of masculinity, they want you to be dominant, to provide, to lead, etc.

Older women are generally less gamey but in other ways they can be more demanding. Older women are more likely to want something serious and settle down.

One thing I learned from my ex is, in EE culture, there's no such thing as "seeing each other". You're either dating, or you're not. Hence why I think you might struggle to have casual sex with a woman like this.

I would proceed with caution. She might not put out next time or the time after that. And in my opinion you shouldn't be ramping up the date quality if she doesn't.