The Wisdom Of Office Romances

Dear Madame X,

Pam Beasley met her husband at work, and this is the new romantic dream for women my age. There are a few candidates in my office but one guy really stands out. We talk and joke all the time about random things, and often have lunch together in the break room. Normally I wouldn’t ask a man out, but my friend said that maybe he wants to make a move but is afraid of sexual harassment problems. I’ve given all the hints I can but short of actually asking him out I’m not sure what to do.

If I do ask him out and he says no I’ll be so embarrassed. I’ll have to see him every day and pretend that nothing happened! What should I do?

Wants to be Pam

Dear Wants to be Pam,

Office romances can be a tricky business because, as you say, if it doesn’t work out then it could get awkward.

So, because of this, you probably want to tread carefully. From what you say he is probably single, but there are a multitude of reasons that he might not be asking you out and it doesn’t necessarily mean he isn’t interested (seriously, The Rules are often wrong).

He might also be worried about making your professional relationship awkward. He might be worried about sexual harassment, like you said. He might be worried you’re only flirting and not interested in anything more (i.e. worried about getting hurt, just like you are). He might simply be shy.

But the thing is, if you don’t make the move you might be missing out on the opportunity of a lifetime and meeting the love of your life (or, at least a few months of great romance).

Let him know, directly, that you are interested in dating him; yes, ask him out!

Let him know that you aren’t sure what might happen but that you think it’s worth risking it to see how things develop. And that if it doesn’t work out or if he is not interested you promise to behave professionally and maturely about it. And then keep your word. If it doesn’t work out make sure to not devolve into high school mind games or rumor-mongering.

Then see what he says. You never know, and, as they say, you will probably regret it if you don’t try and have to wonder for the rest of your life what might have happened.

Madame X is a master of sex. She is adamantly pro-sex which she translates to pro-fun and pro-safety. An avid practitioner of the activity, she has also been trained in the technical dos and don’ts. No mere agony aunt, she knows of what she speaks. Send her your questions, comments, and concerns about sex and relationships here.