Samara O'Shea, love columnist

Dear Samara,

I am a 28 year old and I work in a large commercial real estate firm in New York City. I have a dream job and am getting paid very well. There is guy at work that I am very attracted to and if I am reading the signs correctly, he likes me, too. Our flirting is exciting and I can hardly wait to see him every day. I know this sounds like high school, but my fear is that we will start dating, have a great romance and if it doesn’t work out or even if it does work out, how is it going to affect our jobs? I don’t think dating someone from my workplace is a great idea, but I don’t want to pass by the opportunity of dating someone this fabulous. Any ideas?




Hi Maggie,

There is a scene in the movie How to Make an American Quilt where Finn (played by Winona Ryder) speaks with Anna (played by Maya Angelou). They are sitting on the front porch looking at the moon. It’s obvious to Anna that Finn is about to meet up with a guy and cheat on her fiancé. Their conversation goes like this:

FinnOh, god. Look at that.

Anna: I never liked full moons. They give people an excuse to do foolish things.

Finn: I’m young, I’m supposed to do foolish things.

Anna: And spend the rest of your life paying for them.

Finn: Well, it’s better than spending the rest of my life wondering what I missed.

Anna: I’d rather wonder than kick myself.

Finn: Well, I’d rather kick myself.

That’s what it comes down to: You are either the type of person who would rather wonder than kick yourself or who’d rather kick yourself. Sounds to me like you’re the latter. You’re right in that dating someone at work is not ideal, but you can’t change that reality. Therefore, a risk is required.

I say acknowledge the risk to yourself and then take it one exciting encounter at a time. If the two of you do start dating, speak openly with him about your apprehensions (my guess is he’ll have the same ones).

If it doesn’t work out, there will likely be a few awkward run-ins but eventually you can go back to focusing on work—as you did before you met him. You sound like a consummate professional and I doubt you’re going to let this interfere with your beloved job either way. I hope this works out for you.


P.S. Infatuation always feels like high school—no matter how old you are. Enjoy!