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A life altering change is upon me.....or is it?

Tagged as: Dating, Troubled relationships<< Previous question   Next question >>
Question - (25 August 2008) 1 Answers - (Newest, 6 March 2009)
A male United States age 41-50, *uperDan writes:

I've been seeing this girl all summer long (the same one who had previously made my life miserable), and it's been going well enough, save for her sister in law (aka my best friend) interfering with every aspect of our lives now and again, and now it seems that it's gotten to the point where she wants to become intimate with me.

From the day we met since breaking up last, it seemed she was still infatuated with me, but I didn't quite feel the same about her...actually I had first thought "anybody but HER again!", but the reason I got back involved with her was because my confidence has been so shot, that I honestly feel that I'm not good enough for anybody else. I have crushes on girls who may even be into me to some extent, but for some reason, I'm just deathly afraid to approach them. I feel that my masculinity has taken a horrific beating in recent years. This is due to a combination of reasons:

1) My father and brother abuse me frequently, never missing an opportunity to show me up or shout me down whenever I try to make my own life decisions.

2) My time bomb of a boss at work humiliates me for every mistake I make.

and last but not least...

3) When me and this girl first went out two years ago, the way it ended was due to a misunderstanding which resulted in her sending me a very venomous e-mail, laden with accusations that cut rather close to the bone, and broke my heart severely. Despite the rude tone, I took everything she said to heart.

Now I have dated other girls since then, (not to mention met someone else who I really feel attracted to, and that she may feel the same about me), but they were mostly brief. What I also find intriguing about this situation is that she and a previous ex of mine have so many things in common, it's scary! (this ex is the one I refer to in my question entitled "She was perfect for me, but I still couldn't give myself to her".)

1) They are both in their 30's and are aspiring social workers.

2) They both wanted to see the same kinds of movies I enjoyed (my previous ex saw "Star Wars III" and "Batman Begins" with me, whereas this one saw "Clone Wars" and "The Dark Knight" with me. Freaky, huh?).

3) They're both a bit needy and neurotic.

And at times, I regret not doing the deed with my ex as I now look back and think it may have been fulfilling, but now, with this person back in my life, similar to my ex in so many ways, it's like a second chance. Except, I'm not sure that the person I want to call my first experience should be the same one who made me feel awful previously and has a short temper. Now of course, the easy thing to say would be "if you're not ready, you're not ready", but when she started to go into it with me, I'll be honest, I enjoyed it.

It was a perfect scenario: I had just gotten my best friend to reconcile with me and my date without raising my voice like they do, we went back to my house, where she started to make out with me in my living room, no one else home, and the closing ceremony of the Olympics on the TV :-) She starts maneuvering my hands to rub her in otherwise private areas, and before I know it, she starts (while I'm still clothed) humping me.

...and I chickened out.

At first, I had convinced myself that I wasn't ready to have sex, but now I ask "what if I am"? I mean, she's no prize, but if she's the only person in my life who's showing me the slightest bit of compassion, why not? It would seem like the ultimate case of irony to me, as she was someone I initially denied having any attraction for and only agreed to date because I felt convinced that I wouldn't have a chance with anyone else.

She herself is a very damaged woman: father abused her, past boyfriends treated her like a piece of meat, whereas a guy like me, innocent as can be, treats her well. I sometimes feel like it's my role in life to give everybody everything that I can, whether it comes at my expense or not. So it feels like this is something I HAVE to do to both change her faith in men, and restore my masculinity. But I'm not 100% sure yet. Not to mention that doing so would certainly mean that we'd have to be an exclusive couple, something I've tried to avoid from the get go.

Any thoughts?

View related questions: at work, best friend, confidence, crush, my ex, sister in law

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A female reader, kellyxxx United Kingdom +, writes (6 March 2009):

kellyxxx agony auntYou can't have sex with someone who you don't care that much about. You have personal issues which need resolving before you enter any relationship. X

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