Q: I have recently started seeing someone new, but it's already pretty clear we have a lot in common and there is some major chemistry. We are both very accomplished people, with many talents and experiences that contrast and complement each other's.
However, I believe in a certain amount of modesty and humility, and do not really talk about my accomplishments unless directly asked. He, however, is a walking advertisement for himself. This is sort of part of his life, as he runs a business that teaches men how to be confident around women and put their best face forward. I find it a bit much sometimes. It is the only thing about him that I find unattractive. Could he just be trying to show off because things are new, and he himself is trying to put his best face forward? This could grate on my nerves after a while. Should I say something to him?
A: How about: "The conviction around which you've built your life's work is the only thing about you that I find unattractive."
Your theory about his trying (too) hard to impress you might be a good one. When I see a guy teaching other guys to be confident around women, I see someone who, at least at one point, needed an education of his own. Granted, maybe it takes one to know one.
However, you also have powerful incentive to reject your theory: It would be tough for me to think of seven words that would doom a relationship more effectively than, "Really wanting him to be the one." (Except maybe, "He believes his mother is always right" or "He believes everything is his mother's fault." But I digress.)
It is axiomatic: If you look for the good in people, you will find it. If you look for the bad in people, you will find it. And if you go on dates resolved to find as much good as you need to justify the relationship, then you won't notice the bad until you get the credit card bill from your wedding.
Please, let yourself see him exactly for who he is. (He might not let you, if he's workin' his own program, but that in itself is revealing.)
You won't ever be completely objective, of course, but you can consciously choose not to embrace the first theory that persuades you his annoying behavior is good.
Instead, consider several explanations for the annoying behavior, everything from optimistic to pessimistic to dire to scary to his just being really annoying. That way, you won't get lulled into investing in one outcome or another.
That, in turn, will put you in a better position just to let things play themselves out.
In this case, you do have one other, more concrete option. Since it's his business to brag, get him talking about his business. Ask specific questions about his inspiration, philosophy, slant. If his answers don't give you a peek behind the bravado, his demeanor might. Besides — he's dying for you to ask.
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