Did I miss my window?

Loved those updates yesterday. I'll be writing from New York for the rest of the week. Hopefully from a place with air conditioning. And guacamole. Now a letter …

Hi Mere,

First time writer, daily reader. Please help me figure this out ... I think I have a work crush, but I'm not sure ... it's been a long time ...

A little about me ... I am a woman aged 47, who was widowed two years ago and out of circulation for twelve years prior. It's been a long journey back to the dating world, but I think I'm ready to make the attempt. At this point in my life, I can honestly say I know how short life can be.

There is a man (a.k.a. Smiley) who works at my office and is a laborer. I'm a corporate mucky muck (let's say fifth from the top of a huge organization). Which presents the first issue: is corporate America accepting of this difference in position and social status? I'm not sure he knows how high up the corporate ladder I am. About a year ago he gently started complimenting me, smiling, and getting elbows from his buddy at a company picnic when I walked in (which I saw out of the corner of my eye).

He openly admitted to flirting with me last time I ran into him, a few months ago. I didn't think much about all of this until he left the room a few minutes later with a blush around his collar. At that moment like a splash of cold water hitting me, I realized he liked me. So, OK ... LL commenters ... everybody say it out loud ... "DUH." Somehow I feel the need to admit to my stupidity to you all and say, "How could I have not even acknowledged him?" Especially when I see this 50-year-old man so visibly shaken by little ole me? I've spent months raking myself over the coals about it, and all I can figure out is that I was dealing with so many issues, my grief, estate settling, moving houses and getting children home from college issues ... I couldn't even think about what to say or do. But I do like him, he's nice and sweet and he cared enough to lift me up when I was so down. But I am really out of practice and in new territory here, which leads to issue number two. I felt horrible that I didn’t acknowledged his flirt, so I sent him an e-mail a week ago, letting him know how many times his nice comments have made me smile. Today he stopped by my office and said thank you for the love note, but that he didn't remember what he said to warrant the email and have a good day. Was that his way of saying I blew it, and that he's moved on (to more acknowledging) women?

– Did I Miss My Chance, Massachusetts

DIMMC, do not beat yourself up for the "DUH" behavior. As you said, you were coping with the loss of a partner. It's understandable that you weren't focused on decoding the flirtatious behavior of your coworker.

Maybe he has moved on -- or maybe he's just tentative because you didn't respond to his initial passes. Or maybe he's just having a "DUH" moment of his own. Or, yes, maybe he's a bit wowed by your professional awesomeness. But I'll say this – if he wasn't afraid to flirt with you, he's most likely not put off by your success. And if you've both worked there for a while, he knows what you do for a living.

There's only one way to answer these questions, right? Suggest a social outing. You can ask by e-mail or in person. Maybe: "We should escape the building for lunch today." Or: "It's been quite a week. Want to grab a bite after work?" I mean, what's the worst thing that can happen? He rejects the offer? He doesn't respond? It would sting a bit but at least you'd have an answer
Keep in mind that Smiley could have just replied to your e-mail, but he stopped by your office to talk in person. At the very least, he digs you as a friend. Also know that if you have a crush on someone, it rarely goes away for good. Maybe he's seeing someone else these days, or maybe he's a bit embarrassed and shy, but if he had a crush, it's still somewhere in that brain of his.

You said you know how short life can be. So get to it. And know that if it doesn't work out, it's OK. This is good practice so that you're ready for the next guy whose friend elbows him when you walk by.

Readers? Did she miss a window? Is the crush gone? Is it significant that he stopped by her office? Is he just confused by her unintentionally confusing signals? Is her career an issue for him? Discuss.

– Meredith