Dear Wayne and Wanda,
I'm single and I've had a crush on a woman for years -- our companies work together all the time, so we're constantly meeting, talking and running into each other on projects and at luncheons. We also email funny stuff and gossip to each other all the time. We've always had great chemistry and conversations. But she's been married since I've known her and I would never start something with someone in a relationship.
We had a meeting over coffee the other day, and as we're packing up our stuff, she tells me she always enjoys seeing me and then she gets really serious and says she's sorry for being scattered but she's in the middle of a divorce. I was stunned and excited and sad for her at the same time. I said I was really sorry and put my hand on her shoulder. She hugged me for what felt like forever and then gave me a kiss on the cheek, which she's never done before. Then we left.
That was yesterday and I don't know what to do. Clearly, she's available for the first time, and it feels like I should go for it. She's smart, beautiful and a special woman who I never thought I'd have a chance with. But even though they don't have kids, I know she's dealing with a big mess in her life. I doubt she's ready for a new relationship and I definitely don't want to be just a rebound for her. I already like her way too much for that.
What do you think I should do? Go for it or be a friend or leave her alone? I really want to be with her but something is telling me it isn't right.
- Workplace Romeo
Wayne: Reading your letter, my mind immediately races back to the words of the great 21st century poet Eminem, who faced similar tests in his life as a traveling bard. I think of his immortal words that preface his classic sonnet "Lose Yourself": "Look, if you had one shot, or one opportunity, to seize everything you ever wanted in one moment, would you capture it or just let it slip? Yo."
Go for it, man! Immediately! Yeah, there are pitfalls all around this one. Yeah, she's probably emotionally unstable. Yeah, you might end up being a convenient rebound. But so what? Every new romantic scenario is full of mysteries and danger and potential meltdowns. This is the moment you've been waiting for!
I appreciate your hesitation, and it's awfully grown-up of you for looking before leaping. But these opportunities don't come around every day. Heck, sometimes they never come around. You have been given a gift from the romance gods. Take it and see where it leads. It's not like she asked you to fill in for her husband. Heck, it doesn't even have to be a dating situation at this point. Take her to coffee or a movie or a walk. Be a charming distraction.
Sure, you could stand back, see how it plays out, then make your move. Maybe it will be more inviting down the road when things are a little calmer. But more likely, you're going to find yourself in the friend zone or watch some other guy move in.
If you don't investigate this opportunity, you'll regret it for the rest of your life. And if you don't believe me, take it from Eminem: "So here I go, it's my shot. Feet fail me not. This may be the only opportunity that I got."
Wanda: This lady is not divorced. She's in the midst of a divorce. There is a huge difference between the two. You're mulling whether to move in on your long-time crush. She's staring down the big D and looking at severing ties to the man whom she once pledged to love forever. Even if they're moving ahead with it, there's no guarantee it will go through. And even if the divorce does go through, it will be a long while before she's in the right head space -- and heart space -- to get truly involved with someone again.
Yes, you could be her charming distraction -- a coffee buddy, a movie partner, maybe more. And if all you want out of this is to finally hook up with this woman and cross her off your list of conquests, then go right ahead. But if you really want something more, if you really care for this woman and sense you might share the potential for a future together, then don't make a move just yet. Give her time to plod through this hard time in her life, and keep being the kind, supportive person you clearly are. When the time is right, you'll know. It definitely isn't right now.
• Wanda is a wise person who has loved, lost and believes in retail therapy. Wayne is a wise guy who has no use for therapy. Send them your questions and thoughts at email@example.com.