Writer and comedian Josh Gondelman explains the well-intentioned reasons guys often get grand, romantic gestures so very, very wrong. In college, I was dating a lovely girl for a few months before we went home for summer break. Being the creative gent that I am, I decided to send her weekly packages stuffed with trinkets I came across and letters I wrote as myself or another character . I wanted each mailing to convey that I was fun, exciting, and devoted to her. Instead, I came off, at best, like a desperately needy child—and, at worst, like a serial killer in training."You don't have to send these every week," she told me over the phone. Of course I didn't have to, I said. I wanted to. Isn't that what good guys do? Determined to be more lovable, I doubled my delivery efforts. She broke up with me as soon as we returned to school.Years later, I was dating another lovely woman, but after 18 months, we were on the outs. Naturally, I suggested we take a trip to San Francisco. It would be fun! It would help us fall back in love! Right. It was not fun. We ended things on the last night of the trip.What I've learned? Big romantic gestures are only as strong as the relationships they happen in. If your foundation is solid, then an elaborate proposal will most likely end with a "yes." But if it's crumbling, even the most well-intentioned deed can apply a type of pressure that your bond may not be able to handle. That's why it's important to ask yourself: Is it your partner's efforts that annoyed you, or is it him? Because if it's the latter, chances are you'd still be cranky with him on a private jet while wearing a bathing suit made of hundred-dollar bills. But if it's the former, you can calmly explain to him that comics about a New Jersey rocker are not the way to your heart.Follow Josh on Twitter: @joshgondelmanFor more on how men's good intentions might get lost in translation—and how you can read between the lines—check out the March 2015 issue of Women's Health, on sale now.More from Women's Health:8 Romantic Dates Gone Horribly, Horribly WrongThe Surprising Ways Guys Get Ready for a Date, According to a DudeWhat His Favorite Sex Position Says About Him
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