Wonderful, unattractive friend finds love elusive

(Fotolia)

(Fotolia)

Amy Dickinson, Special to QMI Agency

, Last Updated: 8:36 AM ET

DEAR AMY: My husband's best friend from work, "Billy," is an amazing man. He speaks several languages, has travelled the world and does a million other things. He's also friendly, confident, funny, easy to talk to, nicely groomed and well-dressed, and is a warm, generous guy.

We love him to death, but he can't get a date. The problem is, he's just physically unattractive. It's not any one feature; it's just sort of everything. He's definitely on the low end of homely. He is also short.

I've introduced him to every single woman I know. They like his personality and all agree that he's a wonderful guy, but none of them can get past his looks. (If I had run into him when I was single, I would never have given him the time of day, either.)

I know he's tried every avenue he can think of -- online dating, social groups, singles clubs, church groups -- you name it.

Online is worst. He's had hundreds of women abruptly cut off communication as soon as they see a picture. If he posts a picture at the outset, no one will respond at all.

My husband and I have both run out of ideas for this poor man. I know he's terribly lonely, and it eats at him to be constantly rejected. I think that it doesn't help that he wants to have children. He would make a wonderful father!

He's 44. Is there any hope for him? -- Sympathetic

DEAR SYMPATHETIC: "Billy" might be looking for love in all the wrong places. Yes, he has looked everywhere he, you (or I) can imagine, but has he volunteered to be an after-school tutor (or coach) at the local Boys and Girls Club? Has he looked into being a foster father or a Big Brother? Would he like to try to adopt a child?

What I'm getting at is if this wonderful guy would be a great dad, maybe he should cut out the middleman (or woman) and turn his search toward sharing his life with a child who will value attention, love and companionship as much as he does.

Being a single man is no longer the impediment to fatherhood that it once was. As his biggest and most generous fan, maybe you should engage him in a conversation that could ultimately change his life. Start like this: "Billy, have you ever considered becoming a dad? If you're interested, we'd love to help."

DEAR AMY: I dated a girl in high school for a short time and the relationship ended on good terms. I am now in college and we are good friends (we do not go to the same school).

There is a part of me that is still interested in dating her because I haven't found another woman quite like her, but I am not sure how to approach her about it because 1) I go to college out-of-state and 2) I don't know if she is interested in dating right now.

I don't want to ruin the friendship by saying what I feel if she doesn't feel the same way, but I am also not sure how to approach her about it. -- Confused Bachelor

DEAR CONFUSED: You two have a dating history and a close friendship. This is going to be easier than disclosing your romantic interest to a friend because you've dated her before.

Simply ask her: "Have you ever thought about the two of us hanging out together again?"

She may throw the question back at you: "I don't know, have you?" If so, you can say, "Yeah, I do think about it. But I don't want to mess up our friendship. What do you think?"

DEAR AMY: "Manager" wondered about the awkwardness of choosing not to hire a former associate who did not interview well with a group of co-workers the manager had assembled. You wrote, "I think it is somewhat unusual to be interviewed by potential co-workers."

Actually, it is pretty common, especially in tech fields, to have co-workers interview potential hires. -- Manager Too

DEAR MANAGER: Scores of readers corrected me on this. Thank you all.


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