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Should I bother with the guy of my dreams, even if I know he's a jerk?

Tagged as: Big Questions, Dating<< Previous question   Next question >>
Question - (30 March 2011) 3 Answers - (Newest, 30 March 2011)
A female Canada age 30-35, *42508 writes:

I know this is really really long, if you ever even end up reading it, but I literally just spent 3 hours reading your column and I think you're absolutely brilliant and would love your advice. You don't even have to post it, just a reply would mean the world to me!!

I first met this guy, Tyson, in February of 2010, when I got hired at the arcade he worked at. The minute I saw him, I just felt different, I felt amazing. It felt like I had been picturing this "perfect guy" in my head for so long, never believing I would actually meet him; and then one day he was right in front of me! The only problem: I had had the same boyfriend, Jordan, since I was 15 (I was 17 at the time). I promised myself I wouldn't throw everything away for someone I barely knew. However, I'm a friendly person and Tyson and I became friends on facebook, then started texting, then started texting constantly. I guess you could call it an "emotional affair", we were upfront about the fact that we both had feelings for each other and that if I was single, we would both be interested in spending more time together. We even went for a few late-night drives, but nothing ever happened. The more I got to know Tyson, the more head-over-heels I fell for him. However; my brother, who also worked with us and had gotten me the job, was constantly warning me about him, as were my other friends in the workplace. Things were brought to my attention like a VERY serious drug addiction, sleeping with many other girls in the workplace, etc. Usually things like that are enough to make me snap out of it, but none of it seemed to matter this time. We continued talking, and one day before our shift (and again during the shift) we kissed. I was absolutely elated. However, the guilt I was feeling over keeping all this from Jordan was increasing, so at the start of the summer I came clean to him and broke things off. Tyson and I continued talking, but I was feeling sad without Jordan and he was too busy with the aforementioned drug problem and other girls, so eventually we just drifted apart. A few months later, Jordan and I got back together; and one night while I was at home and Jordan was at the bar, he ran into Tyson. Words were exchanged, long story short, Jordan ended up punching him, knocking him out and being thrown out of the bar. I received a snarky text message from Tyson, never responded, and cut him out of my life entirely, for the sake of my relationship. But I never really forgot about him. And I was always stupefied as to why I couldn't seem to let go of this jerk who seemed like he treated me nice but was actually a terrible person. We were never intimate, apart from that one kiss (if you can even really call that intimacy). I just felt connected to him.

Jordan and I stayed together until November 2010; when he broke up with me seemingly out of nowhere. I went through my dark period, my mourning, crying, not-showering and eating-chocolate-frosting-for-every-meal days. And then I got truly happy. And I still thought about Tyson from time to time. Fast forward to now, March 2011, I look and feel great, and I'm in a wonderful place in my life. I'm 18 years old, just moved to a big city on my own, I basically feel on top of the world. Two days ago, following the advice of my best friend, I re-added Tyson on Facebook, and today we started texting each other. Maybe not the wisest decision, but hey, that's why I'm writing to you! I'm back to exactly where I was before with this guy; only things are a little scarier. First off, I'm not attached to anyone. Secondly, I'm living on my own. And third, after my break up mourning period, I developed a bit of a taste for the party scene; and am now not so "not okay" with Tyson's drug use because I, shamed as I am to admit it, have started to use more than the occasional joint to liven up an evening. Today him and I started talking about how he wants to come visit me in a few months. I have not stopped thinking about him all day, but I'm trying to make myself feel like I have the control this time. It sounds like stupid childish games, but I'm trying to be very breezy and aloof and "I don't care" about the whole situation, when in reality I'm practically bursting at the seams with excitement over this reconnection.

Do you think I'm making a huge mistake by reconnecting with him? Or do you think, as I do, that I feel so strongly for him for a reason, and that I should give him another try? The way I see it, I've dealt with a fair amount of jerks, and once I figure out that they're jerks I'm usually gone. I don't understand why I find him so special.

View related questions: affair, best friend, broke up, facebook, got back together, period, text, workplace

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A female reader, anonymous, writes (30 March 2011):

Short answer: no you shouldn't pursue this.

Why? Because as much as we hate to admit it, us girls like to think that we can be the one special girl who can change a bad boy. In a way, that's probably why you feel strongly about him. Although you know he's a jerk, he seemed interested in you and you can't let go of that initial attraction. If he was a jerk back then, he still is today. What makes you think he's changed? If you're okay with a random hookup, sure go for it. But honestly I can't see this turning into something serious and real. Get yourself out before you get hurt.

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A female reader, TasteofIndia United States +, writes (30 March 2011):

TasteofIndia agony auntNo, you shouldn't mess with a guy who you KNOW is a jerk, KNOW sleeps around and KNOW has a drug problem. Be as smart as you've been with the other jerks and don't get involved with him. Listen to your gut, not your hormones. Listen to your brain and not your heart. You're in a new scene and you'll meet a lot of new people - don't get hung up on the jerk at home who you know is bad news.

Good luck, sweet!

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A female reader, CindyCares Italy +, writes (30 March 2011):

CindyCares agony aunt Long post short answer :

if you have not enough common sense and maturity yet to cross of your circle of friends someone who has a serious drug problem, and on top of that is also a promiscuous jerk, you are not ready to live on your own in a big city and you are headed for trouble.

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