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

[Anonymous]

you're lucky he talked to you

[Anonymous]

I am married now, but years ago I was on match.com and did pretty well (in that I met a lot of nice women with potential for relationship and had a lot of great sex. Probably slept with 20+ women in a 3 year stretch). My theory was to UNDERSELL. The goal is not to get dates, the goal is to get good dates. So I wanted the women the be happy when they met me in person. The WORST thing you can do is put an unrealistic picture, or lie about your age, etc., so that the date is underwhelmed when they meet you.

[Anonymous]

I'd be cautious with this one. Something is off. My guess is he is trying to impress you and that he doesn't really have much else in his repertoire beyond spending money. It's enticing when a guy treats you to nice things. I dated a guy like this, but after a few weeks I figured out it was all about him, not me. He was doing all of it to make himself feel powerful and without regard to what I wanted. Next.

[Anonymous]

Whether or not he has the bucks to back up his story, OP this is a red flag to me.

A man who is telling you already at this stage that he flies private is a man with issues. He is trying to impress you with his wealth (if he really does have it) and why would he feel he has to do that at this stage? To overcompensate for what other area in his life? Is he already insecure before you have even met?

Or maybe he doesn't even have any money, and is using this to draw you in to his web.

Be smart. Meet in a very public place. Listen to your gut. Do not go anywhere where alone with him and do not give out any personal info. In fact, it may be best to let a friend know in advance where you will be.

Something feels really slimy about this guy....

[Anonymous]

I've never done online dating but I did date a lot of very wealthy guys when I was single. I never really thought about it until today but I'm now realizing that none of those men I dated ever bragged about money. This guy puts me off a bit. He might be trying to see how you react. Which is, in itself, unflattering.

[Anonymous]

Anonymous wrote:I've never done online dating but I did date a lot of very wealthy guys when I was single. I never really thought about it until today but I'm now realizing that none of those men I dated ever bragged about money. This guy puts me off a bit. He might be trying to see how you react. Which is, in itself, unflattering.

+1. He's a player assuming you are a gold digger. No offense OP, but you sound impressed with his "private jet" story. I'd put money on his initial end goal being pussy acquisition and then playing with you mentally for kicks. Trust your gut. He's not genuinely into you.

[Anonymous]

Suck his peepee and he will give you an answer

[Anonymous]

I think you guys are reading way too much into this. It sounds to me like your typical guy is boasting a bit to impress someone. Some guys do this more than others. Is it attractive, no. But don't refuse to meet just because of this. Meet in person. You cannot judge someone over e-mail. Meet, have some drinks, talk. If he spends the entire night talking about his travels around the world, his multiple penthouses, etc, sure, cut things off. But you might also find a normal guy who was too dumb to realize the mistake of making that kind of a brag at that stage of meeting someone.

[Anonymous]

Anonymous wrote:I am married now, but years ago I was on match.com and did pretty well (in that I met a lot of nice women with potential for relationship and had a lot of great sex. Probably slept with 20+ women in a 3 year stretch). My theory was to UNDERSELL. The goal is not to get dates, the goal is to get good dates. So I wanted the women the be happy when they met me in person. The WORST thing you can do is put an unrealistic picture, or lie about your age, etc., so that the date is underwhelmed when they meet you.

Exactly ...

My fun car is a classic 40 yr. old Porsche I've had for over 20 yrs. (belonged to my best friend who died in 1990 and I bought it from her daughter). I probably wouldn't even mention it or let a woman see it until at least the 3rd or 4th date because I don't want that to influence her reaction or assumptions about me, etc. Nor would I have mentioned the "flying private" thing, that's a brag of some proportion IMO no matter how you slice it. The 40 yr. old sailboat she'd get to see sooner, it's about the same value as a used Honda (an oldie but a goodie).

[Anonymous]

"He's trying to impress you. I would be wary. Let's hope he's a genuine guy. But I must say, if he's been acting this way and been single for a while- well, I think that's a red flag."

+1. I'd definitely ask about his dating past. I bet he dates lots of women but never for long.

[Anonymous]

Anonymous wrote:

Anonymous wrote:I am married now, but years ago I was on match.com and did pretty well (in that I met a lot of nice women with potential for relationship and had a lot of great sex. Probably slept with 20+ women in a 3 year stretch). My theory was to UNDERSELL. The goal is not to get dates, the goal is to get good dates. So I wanted the women the be happy when they met me in person. The WORST thing you can do is put an unrealistic picture, or lie about your age, etc., so that the date is underwhelmed when they meet you.

Exactly ...

My fun car is a classic 40 yr. old Porsche I've had for over 20 yrs. (belonged to my best friend who died in 1990 and I bought it from her daughter). I probably wouldn't even mention it or let a woman see it until at least the 3rd or 4th date because I don't want that to influence her reaction or assumptions about me, etc. Nor would I have mentioned the "flying private" thing, that's a brag of some proportion IMO no matter how you slice it. The 40 yr. old sailboat she'd get to see sooner, it's about the same value as a used Honda (an oldie but a goodie).

Sucker for a sailor. I can't imagine a more romantic first date. You and me on the high seas... drifting away from reality...

[Anonymous]

Anonymous wrote:I am married now, but years ago I was on match.com and did pretty well (in that I met a lot of nice women with potential for relationship and had a lot of great sex. Probably slept with 20+ women in a 3 year stretch). My theory was to UNDERSELL. The goal is not to get dates, the goal is to get good dates. So I wanted the women the be happy when they met me in person. The WORST thing you can do is put an unrealistic picture, or lie about your age, etc., so that the date is underwhelmed when they meet you.

Wow, I've done this as a woman. I agree. The goal is to have the person leave the date feeling like they've found a gem. Not disappointed in the fantasy.

[Anonymous]

Be careful- I met a guy on Match like this as well. He owns his ownbusiness, likes extravagant things, nice restaraunts, travel, country clubs, etc. it turned out the loser was bankrupt, a deadbeat dad, and asked me for $$$ to prevent him from going to jail.

[Anonymous]

Anonymous wrote:Could be true, but my sense is that it is not. Flying private is just too much of a subtle brag to ring true to me. The best lies to tell are the ones when we give the target a small subtle lie and then let them build the story we want them to believe around that lie themselves.

Who knows - maybe he's all that ... and a bag of chips, but I'm not feeling it. Also, beware of the guys that can't disclosed what they do for a living because they work for the CIA. There's always a few of those around too!

Who knows, maybe Mr. Wonderful really is wonderful!?!?

I hope so, good luck! Just be careful and keep your guard up until you confirm the stories you've been told

"Trust ... but verify"

OP here - will try to answer some of the questions. The 'flying private' while braggy, is maybe not meant to make him AS rich as is he is sounding. Again, assuming everything is true, he has a lucrative job that is directly involved with private airlines (I don't want to give specifics, but - think he's a lawyer who represents them). Thus, I assume he would be flying private through his friends/clients/connections either for free or at some sort of discounted rate - he did not imply he is paying full price for said private flights. I still find it a bit abrasive that he brought it up at all though - could have just said "I'm on my flight home from vacation" instead of "I'm flying private home from vacation."

[Anonymous]

Anonymous wrote:Odds are he doesn't trust you any more than you trust him and he probably intentionally made mention of flying private to gauge your reaction and see if you are indeed a gold-digger.

OP here - I see this could be a possibility, but then what's the appropriate response? I already had him dial-back our first date plans from something more elaborate to just drinks. I told him there was no need to go to so much effort, that we could figure out whether there was any in-person chemistry just fine over a couple of drinks after work.