I'm dating a rumored bad boy. I don't know how to take his reputation.

I'm a smart, assertive woman in her late 20's. I've been around the block enough to know how a man ought to treat a lady and when I should exit a relationship. But the dude I am currently seeing has me wondering what to do. Sorry --- long story, but I feel it's relevant to the whole situation.

About 1/2 a year ago I broke up with my ex whom I loved, but let him go because he felt I was "holding him back." He was very smart & career driven. He was offered a promotion, but he'd have to move clear crossed country for a few years. I didn't want to follow him there & knew that he felt like I was holding him back. We discussed it and decided we'd take a break. I went on a long hiatus where I wasn't seeing anyone & just wallowed in my own self pity. Even worse was a couple months ago he started dating his co-worker out there & they quickly became serous. I never met the girl, but I hated her because I wasn't over him. He was what I considered to be the type of man I wanted to date from here on out. So I went on a lot of random dates with other career guys. Smart guys with goals ... with their heads on straight and money in the bank. Basically none of them fit well for me. They were boring.

A few months ago I met "Charlie." Charlie wasn't really career oriented. He has a job and he's trying to build up his own business, but he was broke & kindof grumpy. We would talk randomly. I instantly liked him, thought he was cute. But it blossomed into something more about a month ago. He was always so polite, respectful, and mild-mannered with me. He knows how to have fun, but in a very moderate way. I was thrilled because Charlie truly treats me so well. He makes me feel like the only girl in the world, and we have a lot of chemistry.

I was always a little taken back my Charlie's friends. They are really rough around the edges. They get drunk every weekend and a few have been to jail for who knows what. They were nice to me, but seem very rough.

I told a acquaintance that I was seeing Charlie. She basically spit her drink out and asked me if I was high. Ummm ... no. She told me everything she knew about him. She said that Charlie is a thug, that he used to deal drugs, that he is a womanizer, that he has a violent temper, that he drinks too much ... etc ect. Basically she told me everything that is a DEALBREAKER for me. My heart just sunk because I can't imagine ... I mean, Charlie? For real? The mild-mannered, gentle guy I've been seeing?

So we did an internet background check on him. It appears Charlie was in jail many years ago for a few years and he has a DUI that was given to him only 3 months ago. He hasn't shared any of this with me. I really like him. I see a guy who is trying to build a future for himself and who truly treats me well ... but I am also apprehensive. I'm thinking of talking to him about what I heard. What do you think?

Updates:
I got rid of the anon. No sense in hiding.

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Most Helpful Guy

  • How does your friend know "Charlie"?

    You have good reason to be suspicious, given the guys he associates with. It is a tricky situation though, given the timing of it all. Have you met with him lately and has he noticed you acting differently? I think asking him is about all you can do at this point, but don't just call him up and confront him.

    When you're out on a date with him, when the moment is right, that's when you say "I have heard some things..." Make it clear that it is all just here-say and that you don't completely believe everything, but that you want to know the truth. If you want to keep seeing him, even if all this is true, let him know that. For all you know, he could be trying to fix himself. Changes like that don't just happen overnight.

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    • She doesn't know Charlie, but Charlie gets talked about a lot apparently. It's hard because the Charlie I know is completely different then his past self, but I don't know him that well yet. I am proceeding with caution. But I like him to much to just cut cords right now. I'm not sure I can bring it up yet. What's alarming to me is the recent DUI. I think it shows that maybe he hasn't changed as much as I thought.

What Guys Said 2

  • D.U.I.. Three months ago. It's recent. It's verifiable. It's grossly irresponsible. Everyone knows its bad, that you don't drink and drive, its widely frowned upon in addition to just being illegal, and at his current age he did it anyway. An activity that gets people KILLED. How wreckless can you get? Don't buy some crap about a couple of beers or just barely being above the legal amount, he was drunk enough to get pulled over and caught, so he was drunk enough. In my opinion, forget all the other stuff - you have your dealbreaker right there.

    Also, I'm voting this for quote of the year. You won, Ms. 2013:

    "Smart guys with goals ... with their heads on straight and money in the bank. Basically none of them fit well for me. They were boring."

    You, ma'am, with a phrase like that are officially the anthem girl for bad boys everywhere and the antagonist of all nice guys on the planet, LOL.

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    • "You, ma'am, with a phrase like that are officially the anthem girl for bad boys everywhere and the antagonist of all nice guys on the planet, LOL."

      You, sir, are reading things into that statement that don't belong. You're putting assumptions in the areas I've left blank. I wanted it to work with them. But they were boring. Just plain and simple. We didn't really click at all. I'm a girl who chases good boys because I consider myself a good, moral woman. I've never dated someone like Charlie

    • Yeah its clear you've dated other people and this guy was a big shocker and isn't your style. I just had a good laugh with that quote because generally mothers urge their daughters to date financially stable men with "their heads on straight" and while they are not all boring, maybe just the ones you have dated, the rejection of such is practically the definition of the bad-boy complex! Even if in your case it happened to be a localized set of unrelated coincidences.

  • Be very careful. Some guys are great at creating chemistry with women to the point that women lose the power of rational thought, and they're usually the worst of the bunch. You've already found out a lot about this guy that's disconcerting. Ignore this at your own peril.

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What Girls Said 1

  • DUI and violent temper - I'd confront him on these, or just pull the plug immediately. He must have done something serious to be in jail for several years. Major red flags.

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    • He was in jail for a year. Not sure what for.

    • Well I believe that with sufficient motivation people can change. But the recent DUI shows poor decision-making and lack of regard - at best, maybe it's not conscious - for the lives of others. I think he has a 'best side' that he's showing you, but will that last once he's 'won' you, and how will he behave towards people you care about? Or just other people in general? I reckon quiz him on what you've heard and keep your eyes & ears open re. his behavior towards others.

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