Older rich man says he wants a relationship?

NSFWSeeking Advice

Not sure where else to ask for advice and very afraid of being judged, please be nice. I come from a wealthy family and have always date people around my age that I met through friends or family. In the last year I have been cut off financially and am struggling a lot with the lifestyle changes.

A much older man who is aware of my situation has started messaging me and saying he wants to “take care of me” but won’t go into any specifics and I’m not sure how to communicate directly. I’ve never been with an older man before and he’s not very attractive. I’m well aware of his finances and he always dates much younger women. He’s a fun person to be around but I’ll need a lot of alcohol if the giving sugar part comes into play.

I desperately want my old lifestyle back and I’ve asked exactly what he’s looking for and he said he wants an actual girlfriend. That’s not something I can do publicly as my family would never speak to me ever again.

We haven’t gone out yet, just messaging.

My question is do they all say “they want a girlfriend” to make it sound better to themselves or do they tend to be pretty direct. Should I ask more direct questions before deciding to meet up with him or go on the date first then bring questions up?

Posted Feb 15, 2026, 10:51 PM UTC

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