If I see a couple together where one is significantly more attractive than the other, my impression of the attractive one is, “She’s not with him for his looks,” (or reverse the pronouns if he’s the hot one). In the crowds I hang with, that normally means she’s with him for his personality, not his wealth.

In a few cases, after getting to know the couple better, I’ve come to the conclusion that the less attractive one was the better catch.

LF asked: (#41)
“I want to encourage him to [be fit and in shape]. Any thoughts?”

Generally the person has to be self-motivated to exercise. If there’s an activity that he enjoys which is good exercise, you can encourage him to do that (without mentioning why). Otherwise, he’s a lot more willing to hear that message from his doctor.

For some men and women, exercise isn’t going to make them trim. One of my buddies cycles to work, takes a spinning class and does 40-60 mile rides most weekends. His pulse and blood pressure are great, but he’s still chunky with a big pot-belly.

Your boyfriend’s diet is a bit easier to alter than his exercise habits. If you cook for him, you can cook healthy meals and smaller portions. You can also keep healthy, lower-calorie snacks around your place.

It’s irrational but it works.

I think you’re worrying about nothing.

Your girlfriend has known you for how long? Does she know you better than the ex-date? Whatever your girlfriend thinks about you, her own experiences with you are going to vastly outweigh the beliefs of a girl who dated you for one hour.

I hate to burst your egocentrism, but the short date probably had little to do with you. I dated one woman for six weeks, then she suddenly stopped returning phone calls or replying to email messages. When she finally showed up again (2 months later), she was apologetic, explained that she’d been overwhelmed by work and other things, and hoped that I wasn’t hurt by her behavior. She thinks I’m a wonderful person (though she’s clearly not interested in pursuing a relationship with me) and would say that to any girlfriend of mine that she meets.

I had another woman break up with me, then later try to set me up with one of her good friends. As another woman explained to me, that means she thinks highly of me. She wants her friend to date someone wonderful, even though she wasn’t interested in dating me.

Your ex-date was not terribly attractive, nor was she successful. So what? If you only dated beautiful, successful people, it would indicate that you were pretty shallow.

Are you really going to have to talk to the “one-hour girl” much beyond saying hello? It was one hour, 3 years ago – I can’t see why you’d have to say anything to your new girlfriend about it other than you met the woman, briefly, a few years back. 

One-hour girl may not remember the occasion as well as you do for one thing, and if she does, perhaps she will be embarrased. I can’t see the topic of rejection coming up at all unless you are the one to mention it.  Be polite to the woman, but focus on socializing with others if possible.