My Boyfriend Doesn’t Own Boat Shoes

I Lived it:

Do we ever really know the person we’re intimate with? Even if you know every little thing about that person, including his middle name, he still could be hiding something—something you don’t want to know. Something like not owning boat shoes.


When I first met my boyfriend, Tad, I thought I had finally reeled in the perfect catch. He was handsome, charming and articulate. But more importantly, I felt he just understood me. Being around him felt right. But the man who comes off as too-good-to-be-true very often isn’t and I was about to discover something about him was very wrong.


Tad doesn’t own a pair of boat shoes. Not even one pair.


I noticed one morning, when Tad had left me alone in his Upper East Side apartment. Maybe I was being paranoid, but I took the opportunity to comb through his apartment just to make sure he wasn’t hiding any big secrets. I was fully prepared to find some weird porn, evidence of girlfriends past—the usual red flags—but what I didn’t find was even worse.



I spent an hour in his closet, searching, doubting myself. They must be here somewhere, I thought. But they weren’t. They were nowhere. I knew he had left wearing sneakers. The boat-shoe-wearing boyfriend I thought I had didn’t exist.


I just don’t understand…how are you supposed to go on a boat without boat shoes?


Trust is an essential part of any relationship. And you should be able to trust your boyfriend to own at least one pair of classic brown Sperry’s Topsiders. I mean, what’s he gonna wear to a casual rehearsal dinner? Dress shoes? Uck, give me a break, you uptight cad! Sandals? NO!!


As I sat in his closet crying and confused, I wondered, how can I continue with this relationship knowing what I know? And why didn’t he tell me? Why did he feel this was a secret he needed to hide? And if I didn’t break up with him before Saturday, what, for the love of God, was he planning on wearing to my sister’s backyard baby shower?!


I love Tad with all my heart and soul. I’ve even pictured myself marrying him, having kids with him, and driving our kids out to the Cape for the weekend, but when I did, I always pictured him wearing boat shoes—not penny loafers or driving moccasins. But once I found out the contents of his closet, I could barely be in the same room as him, never mind a popular coastal destination.


When Tad got back from his meeting, I gave him an ultimatum. He would have to get into a pair of Topsiders before I let him get back into my heart. If he really loved me, he’d realize the error of his ways.


That’s when Tad left me. Apparently, he thought I was being petty and superficial. But I knew I was right. Even though I’ve never met another man more compassionate than Tad, I don’t regret my decision. Because the only thing worse than not owning a pair of boat shoes is being married to someone who does not own boat shoes.