Dear Amy:

I'm 33 years old, and I find myself interested in a beautiful woman 10 years my senior.

We've known each other for years through her friendship with my mom.

"Sarah" was kind enough to lend me her car in order for me to obtain my license, but that was years ago. I haven't seen much of her over the years.

Recently, my mom has brought up her name to me. I'm not sure what to make of this.

Maybe these are hints that she and I should get together, or maybe I'm reading more into the conversation. I would like to get to know Sarah better, but how should I go about this?

I've never had a problem meeting women my age, yet I would feel more than a little weird asking my mom for Sarah's number.

I don't know what Sarah would make of all this, but as long as I'm able to make the initial first step things will fall into place, I believe. If nothing comes of it, that's okay -- at least I tried.

Should I ask my mom for more information about Sarah, or should I just ask for her number?

Is there another way to approach this person, because I certainly don't see it?

Searching in California

The best way to approach a woman 10 years older than you is also the best way to approach a woman your own age. Play to your strengths. I wouldn't go through Mom, other than to learn if "Sarah" is single. Then you can call "411."

Once you get Sarah's number, you'll probably hold on to it for a few days, obsessing over what to say. It might help to loosely script this out.

You should say something like this, preferably as a voice mail: "Sarah, it's 'Searching in California' calling. Your name came up the other day, and I realized it's been ages since I've seen you. I'm working in the software industry now and am really enjoying it. I'd love to catch up. My number is 555-1212 and I hope you'll give me a call. I'm in your area often and could meet you for coffee if you're interested." Beeeeeeep.

There you are. The path to greatness is to just get out there and do the bold thing. Women of any age appreciate guys who are confident enough to cut to the chase but sensitive enough to get the message if they're not interested. It's not necessary to involve your mom. You can take it from here.

Dear Amy:

My mother is a very needy woman, and I get very worn out when I, her only child, visit her or even converse on the telephone.

Every subject matter is full of drama. She is always asking for my take on many matters, and if I answer noncommittally, she becomes offended.

Even though we are complete opposites on the way we approach just about everything, I still care for her a lot because she's my mother.

She has been on antidepressants for about 16 years, and they keep her balanced. She's seen numerous therapists, and most of them just try to put her on more medication instead of finding the root of her behavior.

I love my mom and want to be there for her, but I get so frustrated. Any advice?

Frustrated

At the risk of throwing more therapy at this situation, you might benefit from working with a sympathetic counselor who could help you both understand your mother's ongoing struggle, and also suggest methods whereby you continue to be tolerant but also firm with her. You can deal with her by both affirming her feelings ("I can tell that that really bothers you") and maintaining boundaries ("Why don't we talk when you're less upset?").

You could start your research by reading "Since Strangling Isn't an Option: Dealing With Difficult People -- Common Problems and Uncommon Solutions" (1999, Perigee Trade) by Sandra A. Crowe.

Crowe places difficult people into several categories and makes helpful suggestions on how to cope with challenging personality types.

Write to Amy Dickinson at askamy@tribune.com or Ask Amy, Chicago Tribune, TT500, 435 N. Michigan Ave., Chicago, Ill. 60611.

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