Reply to Online dating - men (especially successful men), how hard do you 'sell yourselves'?

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[quote=Anonymous]I'm a female who has got a date scheduled this week with a guy I've been messaging with for about 10 days. He's very forthcoming about details about his (allegedly excellent) life. It doesn't even really come across like he's bragging, but he's just very different than anyone I've encountered thus far.

Again, all I can go on at this point is what he says, but he appears to be very well-off. Suggesting some really extravagant dates, mentioning that he 'flew private' back from his Christmas vacation, etc. Now, from what I do know about him and his career, it's entirely possible he would have amassed the means and connections to do these things.

He's said I'll be his first online date, so perhaps he just isn't cautious, but if this is all true, it seems like he should be wary of putting it all out there to avoid gold-diggers. Like, even if you can do all of that, would you tell someone (in messages, his profile doesn't mention it) that you haven't even met yet? A lot of women would date him just for the 'perks' even if they weren't all that interested in him.

I've had friends say I am stupid for even questioning this, and that he is just trying to impress me, and it's sweet. I guess I just question whether he might be insecure about something else, or that he expects that I will be so knocked off my feet by the extravagance that I will automatically want to have a relationship with him.

It's not like I expect him to take me to McDonalds on a first date to see if I really 'like him for him' before revealing his true situation. He enjoys nicer restaurants, and so do I, and that's fine. We talked about some of our favorite meals in our messages. It's just that I think some of the revelations (like flying private) weren't necessary.

So, men of DCUM, what say you? If you are a man of 'means' who is online dating, how early does it come up? Why does it come up? Just because it's your lifestyle, and you don't think twice about mentioning it? Or because you are trying to impress a woman? Were you less cautious/aware in your early forays into online dating about revealing information that might open you up to gold-diggers?

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