The Strawberry Letter: Nerd in the Boardroom and Boss in the Bedroom

Dear Steve and Shirley,

I've been messing around with a guy I used to work with. He said he saw something special in me, so he got me transferred to his team. I looked up to this man because of his work ethic and how he commanded the room at our meetings. He's a straight-up nerd, but there's something about him. It’s probably all the big words he uses, but OMG, he's stuck in the late '90s with his hair, his suits, and even the way he talks. Thank goodness he's not like that in the bedroom! He's large and in charge there—he has exactly what it takes to get the job done, and I love how he plays love songs and lights candles before we're intimate. He really sets the mood before he takes off his silky boxers (yes, silk!).

There have been times when I've stared at him sleeping and wondered how he can be both a nerd and a superhero. We've been hooking up on the low for eight months, and no one would ever suspect we're messing around.

Last week, I put in my two weeks' notice because I got a better job. Since I’m leaving the company, he said it's time we get serious and date exclusively. He's 41 and wants to get married and start a family. I’m 44, and I’ve been married before, so I don’t want to choose another man who isn’t the total package. I’m so concerned about how he looks that I told him our first outing should be with my friends.

We did a group date with three of my girlfriends and their men. My girls were very judgmental of him—they said I’d get tired of his nerdy conversation and that it might be too hard to change him. I was thinking new clothes and a haircut could do it, but they’re skeptical.

Can I gradually change a man stuck in a time warp? Would I be a fool to let him go?