Tag Archives: dating

Dear Wendy: “My Boyfriend’s A Bore”

About six months ago, I met this guy, Alex, who I thought was perfect. He is about to graduate law school, he is unbelievably kind, respectful and empathetic, and also the sex is great. But I have slowly begun to realize that Alex is very safe — meaning he’s not spontaneous and not very funny – he’s sort of boring, really. Right around the time that I was realizing Alex’s true colors, I went on a trip to my childhood best friend Harry’s cabin in the woods. We ended up having so much fun and for the first time since we’ve been friends I’ve started to have feelings for him. Nothing romantic happened between Harry and me, but I’m not sure what I should do with my feelings. I feel very guilty being in a relationship with one person when I can’t stop thinking of my best friend. Should I tell both men how I’m feeling? I’m worried that if I tell Harry how I feel that I will lose his friendship, or that it will change things between us. And I’m worried that if I tell Alex he will resent me and think that I was playing a game with him. Please help me make sense of my mixed up emotions. — Between Two Men

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Jake Gyllenhaal And Taylor Swift Are In A Serious Coffee Date Rut

In the month they’ve been rumored to be dating, Jake Gyllenhaal and Taylor Swift have already settled into a pretty blah routine. At first, their courtship had a zip of excitement with a spotting backstage at “Saturday Night Live” and a jaunt to London. But now, the two are clocking a whole lot of time in coffee shops. Which makes some sense because, well, Taylor is only 20 and can’t go anywhere that requires carding. But still, borrrrring.

After the jump, a timeline of how Jake and Taylor fell into their caffeinated rut. Keep reading »

Dear Wendy Updates: “Untouchable” Responds

It’s time again for “Dear Wendy Updates,” a feature where people I’ve given advice to in the past let us know whether they followed the advice and how they’re doing today. After the jump, we hear from “Untouchable,” a guy who was trying to pick up the pieces and figure out went wrong with a recent ex who refused to touch him during the several years they were together. “Was she just not ready for a relationship?” he asked. “Was I a rather lengthy trial run or safety boyfriend?” After the jump, find out how he’s doing today and whether he ever got the answers he wanted. Keep reading »

Dear Wendy: “My Boyfriend Repulses Me”

When I asked my current boyfriend out, I was very clear to explain that I wanted something casual and certainly not monogamous. But somehow, he now thinks that we are a monogamous couple and is planning our future together. He keeps planning for events I don’t want to attend and talking as if we will always be together. He has become repulsive to me and I no longer feel that I want to be in a sexual/close emotional relationship with him but at the same time want to keep him as a friend. With that said, I am currently looking to pursue others outside of my boyfriend, more specifically someone of the same gender. Another complicating factor is that he and I volunteer for the same organization and within the same department, which means I need things to go amicably whether it be a relationship restructure or moving on. How do I get him to understand that we both feel differently about this relationship and its future and do so in a way that will not make it uncomfortable to work together in our volunteer work? Should this be the end? Is moving back to friends a possibility? — Romantically Doomed and Challenged

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Dater X: Playing Patti Stanger On A Bad Date

As I leaned forward and sent my 10-pound ball careening down the center of the lane, I could feel Blondie staring at my butt. Normally, this is a thing I love, but tonight, all I felt was supremely uncomfortable. The pins flew in the air in a jumble, but it was hard to be too excited about the strike. I was on a bad date. And not the kind of bad date where both of you recognize the badness and mutually agree to get out of there as quickly as possible with no hard feelings. It was the kind of date where, while I was repulsed, he was feeling it. Keep reading »

Girl Talk: I’m Dating My Dad

For most of my 15-year dating career, I went for Fledglings, Makeshift Men, pre-release beta tests of the fully formed adult male. Like Rusty, the dread-locked guitarist with groupies to spare whom I followed to various smoky, sticky-floored venues in college, hoping he’d recognize me from anthropology class. Guys whose giant charisma, outsider cool or longer-than-purely-business hair stoked my sense of adventure and ate my own — often annoying — level of maturity for breakfast.

I was drawn to men who were nothing like the soft-spoken, principled and straight-laced person who had been the dominant male presence in my life so far: my retired CPA father. Keep reading »

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