Dear Amy:

I'm a 27-year-old shy guy, and I work for a large company.

There aren't many workers here under 30, but there's one girl in a different department who is 24. We bumped into each other a few months back during a hallway encounter and since then I've stopped off at her cubicle to chat about once a week.

We get along well, and there's been some joking and good conversation. I feel comfortable asking for her phone number soon, hoping to eventually ask her to hang out.

Complicating matters is pending layoffs. Due to a lack of seniority, I am going to be laid off a month from now.

Do you suggest waiting until the layoff occurs, then taking the less-pressurized route of asking for her number to keep in touch?

Or instead of wasting time, should I just suck it up and ask her now? Of course, it would be more awkward because she'll immediately know I'm interested, whereas the other route is a layoff-induced swapping of phone numbers.

I don't want to mess this up.

Co-Worker Crush

There is such a thing as overthinking. You are doing it now.

Let me overthink for you.

If you wait to exchange numbers until you are laid off, you risk subjecting yourself to a "mercy hang out." Mercy hang outs are almost worse than no hang out at all.

Rather than ask for her number, why don't you just ask her out? You might actually find it easier to ask her out, believe it or not, because asking for someone's number is ambiguous (many women don't like giving out their numbers and would prefer exchanging e-mail addresses). If you ask her out, choose something easy, like having coffee during a break or a drink after work. I've recently become a big fan of bowling because it's fun and engaging -- without being too intimate.

If you ask and she doesn't want to go out, it doesn't mean that your friendship can't blossom.

You deserve a lot of credit for trying to tackle your shyness. I know that it is very difficult for you, but a lot of people find those very qualities that make this encounter challenging very attractive. Go for it.

Dear Amy:

I sympathized with "Virtually Challenged," who was bothered by people sending him forwarded inspirational thoughts despite his request that they not do so.

I have a very close friend who forwards everything he gets from everyone. Often these messages have passed through many computers and sometimes pick up viruses that they then pass along. My partner and I recently had to rebuild our hard drive because of this.

I let my friend know this and told him that I would be deleting these things, unopened.

He understood, still sends them, and I delete them.

It is easy to tell, because the subject line of the e-mail contains an indication that it has been forwarded.

Michael in Chicago

If you have asked someone to stop forwarding e-mail and they refuse, then it's time to employ my favorite key, "Delete."

Dear Amy:

More on grandparent nicknames.

I come from a large family. My mother had six siblings and she was the youngest.

My oldest cousin named our grandparents Big Mama and Big Daddy, and that's what all the grandchildren (13 of us) ended up calling them.

Missing Big Mama and Big Daddy

This is right out of Tennessee Williams! Thanks for writing in.

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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