Sex & the Single Woman: Bah Humbug

All week we will be posting stories from Sex & the Single Woman’s Worst Boyfriend Of All Time contest. The winner with the most comments (minimum 5) wins a Breakup Gram from Girlfriend Grams. Start voting now, or email to share your own bad boyfriend story!

I was with my on again, off again boyfriend of four years shopping for Christmas trees. This was his way of showing me that he “cared,” by doing an annual good deed. Never mind the fact that he was out with the “boys” the other 364 days of the year. Anyway, I don’t know why I was so hung-up on this guy—he was an all-around bad guy. Separated from his wife, five children, womanizer (obviously), hung out with all the neighborhood losers, etc.


Two weeks before Christmas, we went shopping for the tree. Found the perfect one, we hugged, we smiled, etc. So we pull up to my apartment building (which he recently moved out of during our last “off-again” cycle) and he scurries into the lobby. I yell, “Hey, what about the tree?” He yells back, “Carry it up, I have to pee.” Seriously, it wasn’t a huge tree, maybe about four feet, but still! I have to carry this thing up three flights of stairs? I’m only 5′ tall myself—awkward doesn’t begin to explain it.

I finally get upstairs and he meets me on the top of the second floor to “help” me get this tree upstairs. Anyway, we get it upstairs, he helps me put it on the stand, and he says “Gotta go, maybe I’ll see you tomorrow.” Okay, this hurt too. But it’s still not the devil boy part.

The next day I was meeting a girlfriend for my huge X-mas shopping day. I had been in a rut with all the breakup and make-up stuff that I hadn’t even had a chance to buy a single gift. Maybe a little retail therapy would make up for all the crap I’d been dealing with.

We drive to the city, headed for Macy’s, picked out a few things for my family, you know, sweaters, jewelry, the norm. Waited on two-hour lines, about to feel accomplished and proud that I got something done.

Here’s the fun part…my money was gone! All my hard-earned cash that I saved for this special day. Around $1200, give or take a few bucks. I had my purse upstairs the day before when we went to go get a tree. He knew this because he questioned where my purse was. Since the tree place was only down the block, I just stuck $40 in my pocket and held my keys.

A few months down the road the truth came out (although I knew all along) and needless to say, that was the end our relationship.