Tag Archives: rebounds

Dear Wendy Updates: Rebound Guy 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 Rebound Guy, who was always falling for women who had just gotten out of long-term relationships. When he wrote, he was involved with one such woman who kept telling him she wasn’t ready for a relationship. After a year and a half of seeing her off-and-on, he was beginning to wonder if she’d ever be ready. So, did he decide to move on? Did she eventually come around? Has he finally kicked his habit of dating recently broken-up women? Find out after the jump. Keep reading »

Dear Wendy: “Always The Rebound, Never The Boyfriend”

Just about my whole life I have been the “rebound guy” for most of my relationships. I have a knack for meeting women who have just exited a long relationship and once I help heal their broken hearts, I’m dumped. For the last year and a half, I’ve been dating a woman who, you guessed it, was just out of a four-year relationship when we met. Learning from past experiences, I didn’t hold any expectations or try too hard to get a commitment. As such, our relationship has been pretty on and off: we’ll go on a date, then she’ll disappear for a few weeks, then I’ll hear back. Rinse and repeat. I know I have not landed this plane crash in the “friend zone” because there is sex. Whether or not I veered into “booty call zone” is unclear, though certainly possible. When we first started seeing each other she specifically mentioned she was not looking to get back into a relationship, which I totally understood and agreed with. So my question for you would be this: what is the statute of limitations when it comes to a rebound relationship? Is the next person you are with after a long relationship automatically the “rebound,” be it three months or three years later? Should I let her get the “rebounding” out of her system with some other schmuck and then I’d no longer be the rebound? But then, if I do that, I run the risk of her meeting Mr. Anti-Schmuck neurosurgeon who owns three yachts. And, maybe, I was already the rebound guy and there’s no hope? — Rebound Guy

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How To Get Over Your Ex With Craigslist

My boyfriend and I had broken up, and my heart was in pieces.

I needed a weird and fluky experience to distract me from reality and test my ability to feign composure. And, as we all know, the first step in getting over heartbreak is random sex. What better way to combine sex and weirdness than Craigslist, where people hook up based on absolutely nothing — luck, timing, fate?

I consulted my Meaningless Hookup Expert, aka my Best Gay Friend, to formulate a plan; presented here for your gawking/edification is our first-hand guide on how to have a cathartic, post-breakup, strings-free CL hookup. Keep reading »

The Breakup Diaries: Five Ideal Rebounds

I am almost — oh hell, really — ready for my first post-heartbreaking split rebound. Some are surprised I’ve ever waited this long, but, frankly, I’m nervous about even kissing someone new, let alone, um, other stuff. Vaguely excited though too — I was, after all, going to go the rest of my life only being with the same person (which was fine by me!) but there is something oh so thrilling about the unknown. That said, unless you have a heart made of pure steel, the rebound requires much caution — the last thing you want is to A) end up falling in love so soon again, B) have someone fall in love with you, or C) cause further life drama. After the jump, five of the safest — but still exciting! — rebound types… Keep reading »

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