Dear Tell All: My ex-wife and I raised our kids in a tight-knit neighborhood on Madison’s west side. We were close to several families with children about the same age, watching them grow up from infancy to college. We were constantly at each other’s houses for dinner and often took vacations together. My wife and I split up after our kids went to college, and I moved to a different neighborhood. I don’t get together with my old friends as much anymore, though we’re still in touch.
Recently, one of them asked if I could help his daughter get a job at my company. This young woman — I’ll call her Maddie — graduated college last spring, and I hadn’t seen her in a couple of years. We set up a lunch date so she could tell me about her qualifications and I could tell her about the company, where I’m a middle manager.
When we sat down, I was stunned by how poised and beautiful she’d become — no longer the skinny, awkward girl in braces from our neighborhood get-togethers. We hit it off, and I thought I perceived a spark between us. I’ve dated women my own age since my divorce but never felt a connection with anyone the way I did with Maddie. The lunch stretched on for two hours and ended with — unless I’m fooling myself — a bit of flirtation.
I went all out to help Maddie get a job at our company. We’ve grown even closer during the month she’s been at work, and I’ve even started a Snapchat account so we can communicate outside of the office. I think about her constantly, to the point where I’m falling in love. If she weren’t my friends’ daughter, I would ask her out immediately. We’re both single, we share similar interests, and now we have the workplace in common.
But I’ve been holding back, for better or worse. Given that this might be one of my last chances for true love, do you think I should go for it?
Gray Fox
Dear Gray Fox: The thing you should “go for,” my friend, is therapy.
It’s painfully clear that you’re deluding yourself. Maddie is almost certainly not flirting with you. She is almost certainly not waiting for you to ask her out. What you mistook for “a spark” is simply a comfort level — the result of all that time you spent with her and her family. Not to put too fine a point on it, but why would an attractive recent college graduate want to hook up with a desperate middle manager her father’s age?
I suspect that loneliness has led you down this crazy path. But I see hope in the fact that, thus far, you’re holding back. It suggests you aren’t completely divorced from reality. Muster whatever rational brainpower you have left and try to envision how Maddie’s parents, your ex-wife, your kids, and your co-workers would react if they learned of your romantic intentions.
Forget about Maddie and recommit yourself to your dating women your own age, Gray Fox. Your true love is out there, and she probably isn’t on Snapchat.
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