Tag Archives: breaking up

Dear Wendy: “I’m Afraid To Leave My Fiancé”

I have been in a relationship for five years, since I was 18. We got engaged about two years ago but have yet to set a date (basically because I don’t want to). The truth is, I contemplate leaving him almost daily. Why don’t I just do it then? Because I am terrified of hurting him, hurting our families, being alone, and one day regretting that I left him only for it to be too late by then. I have tried to break up with him a few times since we got engaged, but it always morphs into a “break” where we still talk often and then we easily slip back into our old relationship routines. I haven’t been without a boyfriend since I was 14, so the thought of being alone scares the bageezus out of me. What makes leaving the hardest, though, is the fact that he is such a good man who treats me wonderfully and also happens to be my best friend. There are so many things about him that love, but I don’t love him the way that I should love the person I’m going to marry. How do I leave someone who treats me so well, who hasn’t done anything wrong, and who I enjoy spending time with, only to live life alone and uncertain if I will ever find someone better than what I already have? — Reluctant Bride-to-Be

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16 Awful Places And Times To Dump Someone

Story time! The summer after my sophomore year of college I dated a guy whom I had more of a sexual connection with than an emotional one. He was one of the first guys I met who was genuinely into S&M and we enjoyed exploring each other’s sexuality in exciting and painful new ways. But I didn’t want to have intercourse with him, so he decided to dump me over that. Great guy, I know. This piece of work took me out onto Long Island Sound in his parents’ motor boat under the pretense of having a nice sail together and ended the relationship out at sea. Then he dropped me off on a pier and sailed back to shore. Cuh-ra-zy. Keep reading »

Dear Wendy: “Why Didn’t She Want To Be Close To Me?”

My last relationship ended badly and I’m looking for some clarity. All throughout our time together (on again, off again over a period of several years), she seemed impossible to get close to. Whenever we hung out at her place, she always kept her overprotective dog (who would growl whenever I got near her) close at hand and, when we’d go to my place … well, one night we’d be cuddling on the couch watching television just fine and the next I couldn’t get within three feet of her without her hopping up for a drink and settling back down across the room. It took quite a while for us to get physical and, once we did, she started making excuses and becoming distant. Finally, after confronting her about it, she threw it on me for being “too clingy” among other things that I just didn’t get, and we proceeded to never speak to each other again. Even after several months I’ve still got this nagging itch of confusion that just won’t let me go. I mean, was she just not ready for a relationship? Was I a rather lengthy trial run or safety boyfriend? Any thoughts? — Untouchable?

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Dear Wendy: “Should I Befriend My Ex-Boyfriend’s New Girlfriend?”

One of my first really serious adult relationships happened when I was in my early- to mid-20s. We ended things after about three years, two of which we spent living together, and although our breakup was extremely heart-wrenching and hurtful, over the years we have been able to develop a much stronger relationship as friends. When he started dating his current girlfriend last summer, I wasn’t surprised when I didn’t hear from him as much (previously we had been hanging out an average of twice a week, sometimes more) because sometimes that’s just how things go when you meet someone new. But as the six month mark passed and my conversations with him were few and far between, I began to wonder what the deal was. He confided in me that his girlfriend had trust issues — MAJOR ones. (She was checking his browsing history on his computer, she made him de-friend me on Facebook, and every time he brought up my name or made an attempt to hang out with me, an argument would ensue.) They’ve been dating a year now and I’ve still never met her. The last time I talked to him — we’ve managed to see each other a handful of times since he started dating his girlfriend — he mentioned that he is thinking of proposing. I would like for his girlfriend to get the chance to know me. Additionally, I know my ex misses our friendship and still cares about me deeply, enough so that he has always stuck up for me and made sure she understood that her jealousy and trust issues were HERS, and not caused by anything I did. Should I make an attempt to befriend his girlfriend so that she becomes more comfortable with me? — The Ex

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Dear Wendy: “Is My FWB In Denial About Our Relationship?”

I’ve had a “friends with benefits” situation with a male friend of mine for the last few months. I recently told him that I had feelings for him, but that I was in no way interested in acting on those feelings, as I know that he is not wanting a “gf/bf relationship” right now. After I told him this, he told me he needed some time to think things through. A few weeks later, he invited me out for a few drinks, and then back to his place for the benefits part of our relationship. We went out for a middle of the night snack, and he did all of the classic “boyfriend” posturing — opening doors, hand brushing, turned toward me, looking at me during conversations, etc. After that, he has been contacting me almost daily, first for benefits and then for cuddles and talking. Last week, he invited me out for karaoke at a local bar where he introduced me to people (as his friend), but spent the whole night with his arm around me. At one point, he even kissed me after I performed. But he still insists that this is a FwB relationship, and nothing more. Oh, and he isn’t seeing any other women in any sort of capacity. He is in denial over our relationship, or am I just way too into him? — Just a Friend with Benefits

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Dear Wendy: “Is It A Bad Idea To Move In With My Ex And Her Boyfriend?”

I’m planning on moving in to a new apartment with two close friends in a few months. We’re all in our mid-20s now and hang out on a weekly basis. The two of them have been dating for a little over two years now, and like the idea of sharing an apartment with a close friend before moving out completely on their own together. I’ve been friends with the girl for about nine years, and the guy for about six, and was actually the one who introduced them. The girl and I also dated for about two and a half years, but broke it off over three years ago, while still in college. After a cool-off period, we slipped back into our previous friendship far better than either of us expected, and have been extremely close since. While I’m not worried about living with the two of them, some of my family and friends think it’s a bad idea. I have no desire to get back with her, or really to change the relationship we currently have in any way. We actually lived together our senior year of college (after the breakup) with another mutual friend. That all worked out rather well, despite the obvious concerns to the contrary, so I feel we definitely have some past experience to believe there shouldn’t be any significant problems living together. Do you think having an intertwined past could prove problematic when living together? — Cautiously Optimistic

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