Dear Wendy
Dear Wendy

“Once a Cheater, Always a Cheater?”

I’ve been talking to a guy for about four months over the internet, Skype, and phone. We met once when we were both in relationships (he was one of my ex’s friends) and I instantly liked him as a person, and he later admitted he felt the same, but we never really talked much until we were both single. We have amazing chemistry from what I can tell, and are planning to meet up this summer. He’s currently living in another country, but will be moving back to the states in a month or two. We’ve talked about the possibility of being in a relationship if all goes well when we spend time together in-person. The only thing is, he admitted to me that he used to be a cheater. He told me he has cheated on girlfriends in the past, including his most recent ex, whom he was in a long-term relationship with. He said he’s really been making a point to change, and so far has been completely honest with me whenever I ask him questions about anything, even when it would be easier to lie and put himself in a more flattering light. I’m hesitant because of his unfaithful past, but I feel like him telling me about it all is his way of coming clean and laying it all out there for me so we can start off our relationship without any secrets. Should I give this guy a chance, or is it true that once a cheater, always a cheater? — A Little Leery

You live in different countries, he’s friends with your ex, and he’s a repeated cheater? Sounds like three strikes against him if you ask me. Four strikes if you count the fact that you’ve only met in person once. Sure, one way to spin things is that he confessed his cheating past as a way to start off your relationship without any secrets. A more realistic way to look at it, is that he told you, so that months down the road when he confesses that he’s now cheated on you, he can say, “But, baby, I told you from the start that I have a problem with being faithful. I warned you.”

When someone tells you who he is, believe him.

I’m a grad student in my early 20s and met a great guy over spring break. He asked me to dance at a blues dive and we got drawn into an engaging, open conversation that didn’t stop until the bar closed. We made plans to hang out the next day and saw each other every day after that…until he flew back to school several states away. Now I’m unsure what to do. I was very attracted to him and we connected instantly in a way I’ve never experienced before, but I’m not sure if he was interested in me romantically. Although the conversations were a bit flirtatious, he never made a move and we didn’t so much as kiss before he left. I’m used to dating guys who are fairly clear about their intentions and I wasn’t sure where I stood in this situation. Despite that, I felt like we really hit it off and I would be willing to take a chance on him. Am I crazy for thinking of starting something long distance, especially when I’m not 100% sure of his feelings for me? How should I approach it when he lives so far away and I’ve known him for so little time? — A Confused College Girl

I’m going to answer your question with a question: what do you think the percentage is of relationships that begin when both parties are 100% sure what the other’s feelings are? My guess is: not many. In the beginning, you aren’t even sure what your own feelings are. So don’t let your uncertainty about this guy’s intentions be the thing to stop you from pursuing something. I say send him an email, or call him up and tell him how much you enjoyed meeting him and that you felt a real click with him and wondered if he felt it too. If he’s at all interested in pursuing something long distance with you, he’ll let you know. If he’s not, then at least you won’t have to keep wondering “what if?”.

34 comments… add one
  • _jsw_ March 24, 2011, 3:14 pm

    I completely agree with the advice to LW2, but for LW1, I’d say it wouldn’t hurt to see how things go. People cheat without admitting a prior record of it, and people who have cheated in the past don’t necessarily cheat again.

    Yes, granted, he might just be setting up a future excuse. And I definitely wouldn’t get too involved too quickly. But as long as you always keep in mind what he’s told you*, I think you should feel OK at least checking out the waters when he gets back.

    * I suggest writing “once a cheater…” on his lower stomach in permanent marker every time you agree to have sex with him.

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  • Golden_Key March 24, 2011, 3:19 pm

    Great advice on both accounts, Wendy!

    @LW!–This is not worth it. If he had cheated once, perhaps. But at this point, he didn’t “used to be a cheater,” as you put it. He is a serial cheater who has not yet shown he can be in a relationship without cheating, especially if he just cheated on his long term girlfriend who is his most recent ex. Also, although it may seem like he’s being very honest with you, it’s hard to know if he is truly giving you the whole story since he is still living in another country. I just don’t think this guy has given you enough reasons to trust him, and I doubt he will anytime in the near future. I really wouldn’t put much stock in him saying he’s changed. Often the people who tell you how honest they are on a constant basis are, in my experience, the ones who are duping you. If he’s really such a great person, he would be able to show you through his actions rather than reassure you with his words.

    @LW2–Go for it! What do you have to lose besides a little bit of pride? Good luck, I hope it all works out for you!

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  • ReginaRey March 24, 2011, 3:22 pm

    LW1 – I’m pretty wary of people who have a long history of cheating. If he had cheated one time on one girlfriend, that could possibly be overlooked (or at least forgiven). But if he’s cheated on *multiple* girls, as he’s said, do you ever feel you could fully trust him? If you’re leery RIGHT NOW, before you’ve even started dating him, how much more leery do you think you’ll be when you have strong emotions attached? If you don’t think you can handle not knowing where he’s going or who he’s with at all times (and you *shouldn’t* have to know where he is and who’s he with 24/7 in a trusting relationship), this isn’t the guy for you.

    LW2 – There’s no reason not to contact him. Not every encounter ends with you being 100% sure where you stand. That said, if you contact him and get little or no response, MOA. If he’s into you, he should be reaching out to YOU about half the time, in my opinion. Also, is this long-distance a permanent thing? I’m not saying it’s impossible, but it would be extremely difficult to build a relationship off of a few-days-worth encounter, when there’s no end in sight for the long-distance. But hey, if it turns out he’s estatic that you contacted him, and he keeps up a steady stream of communication (as in, he initiates communication without prompting from you all the time), you guys could decide to travel to see one another on a regular basis. It’s not out of the question. Just be sure he’s as invested in it as you are if this is something you do want to undertake.

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      caitie_didn't March 24, 2011, 6:00 pm

      I was able to build a pretty successful long-distance relationship off of a few days of face-to-face contact! Granted, we were able to see each other quite often, but we really got to know each other by chatting on Skype/Gmail chat before dating for a few months and then making it official. We’re not together now, but the ultimate reason for that was nothing to do with distance so I say LW2 should go for it!

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  • CG March 24, 2011, 3:43 pm

    I’m going to disagree with the advice on LW2. You and this guy hung out for several days and had great conversations, but he never tried to make any sort of move? And now you’re back to “real life” and he’s several states away and, unless I’m reading the letter wrong, he hasn’t contacted you? Not to sound like a cliche, but he’s just not that into you, girl. MOA.

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    • convexed March 24, 2011, 11:02 pm

      That’s a possibility for sure. Another angle is that, knowing he lived several states away, he didn’t want to complicate a straightforward positive encounter with a romantic/sexual move that might not lead to anything. It’s always possible to meet a guy who, weighing it out, knowing the logistical difficulties of distance, would rather have the great conversations with a like-minded person to look back on than the one-night stand with the awkwardness that could bring as well as closing down the possibility of reconnecting later with a clean slate.
      Guys are of course people too, and not only driven by hooking up. He could easily be the pragmatic type who is thinking, “We really hit it off. If we lived in the same town I’d totally ask her out.” He might not see a practical purpose in making contact, rather just let a pleasant memory be just that. It might not have occurred to him to try a romance, especially if he doesn’t generally do long distance.
      So, nothing may come of it for LW2, but that doesn’t necessarily mean he wasn’t into her.

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      • Fairhaired Child March 26, 2011, 2:51 am

        Also I’d like to point out that depending on his upbringing he could be very cautious about making the first moves on girls. Esp. if it may seem that (as you said) they would only know each other for a few days. And though they may have talked and had great conversations, perhaps he has someone back at school (that is dating currently or wishes to date).

        But as other posters have stated- she could totally reach out to him. Plus since he IS long distance, if she gets egg on her face from his rejection, then its not like she’ll have to see him every day walking to class and go “oh god we had such a great friendship talking and everything now i’ve mucked it up and i’m all embarrassed that I wanted to persue things farther and he didn’t” every time she sees him.

  • Maracuya March 24, 2011, 3:47 pm

    LW1- I don’t know. If it was a one time thing that he felt remorseful about, I’d say give it a try. But if he’s cheated on girlfriend(s), including his last long-term, I’d say that it’s more likely that he hasn’t learned from his mistakes. Did he say why he did it? I would also be more than a little leery, and quite frankly, would probably avoid. I don’t think that ‘once a cheater, always a cheater.’ I think it should be looked at on a case-by-case, but I also think that there’s a difference between forgiveness and naivety.

    LW2- Go for it!

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  • TheOtherMe March 24, 2011, 3:49 pm

    About letter 1. Once a cheater always a cheater ? NO, absolutely not, but there is a difference between “once” and a pattern of cheating multiple times on multiple partners. Also, he’s saying that he’s honest with you about anything you ask but he was probably not as honest to the other person at the time he was cheating.

    Maybe he does want to change, but can you accept being his “I’ll try to be faithful to this one” girl ?

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  • silver_dragon_girl March 24, 2011, 4:21 pm

    “When someone tells you who he is, believe him.” This. 1000X this.

    I’d feel differently if you’d been talking to this guy and asked, “Hey, have you ever cheated?” The “well, actually, yeah” answer would be a bummer, but worth a chance, perhaps. But the fact that he went out of his way to inform you that he “used to be a cheater.” Including his most recent ex. Guess what? That means he IS a cheater. He only gets to “used to be” a cheater once he’s been in a relationship and proven that he can keep it in his pants.

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      Heather March 24, 2011, 4:32 pm

      I love your last line. I think that’s a really fair statement.

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    Heather March 24, 2011, 4:22 pm

    I don’t think any situation is black and white. I have personally cheated before, but the last two guys I didn’t. And I personally would be pretty upset if anybody had the nerve to tell me that because I had made mistakes like that before, that automatically made me a bad person and meant I was going to do them again.

    Having said that, LW1, this guy told you straight up that he’s had lots of issues before. I do think you should give him a little benefit of the doubt (if he comes off as sincerely sorry and willing to change), however I would proceed with caution. I would never suggest you deserve to get cheated on just because you took a chance with him, but I honestly wouldn’t be too surprised if it happened.

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    • maynard March 24, 2011, 5:02 pm

      I agree. I’ve cheated before – but when I was younger, not in what I would call a “serious” relationship, and it wasn’t something I did on a regular basis (meaning I realized I cheated because I wasn’t happy in my relationship then ended the relationship, I didn’t continue to cheat just because I could, or something)

      Clearly I’ve got some personal biased, but I think what I did in my ‘youth’ is different from repeatedly cheating on a long-term partner (which is something I definitely haven’t done). I guess I’m saying I feel like the ability to continually lie to and betray someone you’re in a real relatioship with typically takes a certain kind of persoin, and I don’t know how quickly that type of person can change.

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  • Tracey March 24, 2011, 4:24 pm

    LW1: Exactly how do you know he’s being truthful to you? You’ve only met in person once, and the rest of your interactions have been through media where a person can be anyone he/she wants to be. I’m not saying he’ll always be a cheater, but I am saying take his history into account, and really pay attention to him when you get the chance to interact with him in person. Actions speak louder, and more truthfully, than words. In the meantime, keep your options open and date others. Dont’ be in a rush to get into a relationship with this guy. If he really wants to be faithful to you, let him show you, not tell you.

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    Jess of CityGirlsWorld.com March 24, 2011, 3:45 pm

    LW1, I think the question I would ask myself would be, “Knowing what I know, will I be able to fully trust him? Can I go into this relationship offering him the full benefit of the doubt?”

    Sometimes this kind of information poisons the mind. Even if he never cheats again, will you wonder every time he stays late at work or falls briefly out of touch?

    I’m afraid I would.

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      caitie_didn't March 24, 2011, 6:09 pm

      oooo….good point.

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    sobriquet March 24, 2011, 4:50 pm

    LW1- “He said he’s really been making a point to change” … which means he hasn’t actually changed yet. Key word! That’s my major problem with this. He’s basically telling you that he’s a cheater and although he doesn’t want to be a cheater, that’s who he is. Eek.

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    • thyme March 24, 2011, 6:08 pm

      Yeah, that was the red flag for me. People change, but this guy actually told you that he HASN’T changed yet. Let him work on his “issue’ without you having to be part of it.

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  • Steelbird March 24, 2011, 5:52 pm

    LW1 – Run, run far away and don’t look back. I have lived this story. I dated a guy who admitted to cheating on his girlfriends, but he said I was special and he wanted to change. I figured I could be the person to help him change. Several months into our relationship he admitted to cheating on me with his neighbor, like an idiot I forgave him. He cheated on me again several months after that. I ate up all of his excuses time after time. My biggest regret is that I never had the guts to tell him to hit the road. I sat around until he finally found another girl who believed he would change for her and he broke up with me. All of my friends tried to warn me that he wasn’t a good guy but I wouldn’t listen to them, in fact it made me more stubborn to stay in the relationship, I hope this advice doesn’t do the same to you.

    LW2 – Give the guy a call, let him know you thought there might have been something there and see what he says. The worst thing he can say is he’s not interested and since he doesn’t live in the same state, you don’t have to see him.

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    caitie_didn't March 24, 2011, 6:07 pm

    LW1, I on-and-off dated (for three years!) a guy who freely admitted to me that he “had commitment issues” before we started dating, but “really wanted to make it work”. Yeah…..it really didn’t. And like an idiot, for three years I kept believing he was *really* going to try that time around. And, exactly like Wendy said, when the inevitable breakup happened, he’d tell me “but you know I have issues with commitment, so I don’t understand why you’re so upset”.

    If I were you, I’d drop this guy like he’s hot, and I’d probably tell him exactly why I was no longer interested in him. Like other people have said, he didn’t *used* to be a cheater, he *is* a cheater. Tell him once he’s proved he can keep it in his pants you’ll give him a shot.

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  • Desiree March 24, 2011, 6:37 pm

    I wonder if the guy that LW2 met has a girlfriend back home. It seems that a spring break fling with a girl he has chemistry with would be hard to resist. But, if he has a girlfriend, he might be a good enough boyfriend to not cheat, but not forthcoming enough to acknowledge the girlfriend. There are other possibilities, this is just one I thought of.

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  • demoiselle March 24, 2011, 7:19 pm

    People often tell you what they are at the beginning of a relationship. Unfortunately, most of us choose not to listen…

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    • Kerrycontrary March 24, 2011, 11:47 pm

      Well said!!

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    fast eddie March 24, 2011, 8:09 pm

    Long, long ago I cheated only once and hated doing it at the time. GF1 was hundreds of miles away and we had no agreement to be exclusive. GF2 was local and knew about GF1. I felt that I was being unfair to both of them and myself. I lost both of them in the end. Never did that again, it was just too draining.

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  • kiwi57 March 24, 2011, 10:33 pm

    My boyfriend of two years confessed at the beginning of our relationship that he had cheated on all his girlfriends in the past. It opened my eyes, sure, but it didn’t change the way I saw him or how I felt about him.We’ve had to do periods of long distance throughout our relationship, but we’re still together two years later and he has never, ever cheated on me and I trust him completely not to. I think for him the big difference was that he really loved me and saw our relationship as the real deal, and he knew he wanted to marry me down the line. I guess you could say I took a risk by continuing to date him after his admission of past infidelity, but it’s a risk I’m so glad I took because I love him more than anything and I know he feels the same about me. I guess you have to ask yourself, LW1, is this a risk you’re willing to take?

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  • convexed March 24, 2011, 10:54 pm

    This might sound cynical, but there’s a chance that his promise/insistence that he is totally honest with you is his way to get your guard down in advance. As a serial cheater, he’s used to having to cover his tracks and is probably used to his girlfriends getting suspicious about his shady behaviors/whereabouts/double life. So, if he sets the stage for you to trust him, to have an investment in seeing him as honest, when the inevitable shady behavior starts up, you’ll be second-guessing yourself, not him. He’ll be able to say, ‘But I told you I’d always be honest, remember? So why don’t you believe me?’ and you’ll be trapped in this awkward position of having entered a relationship on the terms of taking his word as truth, and now backing down from your part of the agreement. If that is his move, it is extremely manipulative and the mark of a professional, committed cheater. Or it may sound like my theory is super-paranoid, but with admitted cheaters, you need your paranoia up and running to see through their wily faux-repentance tactics and redemption-in-process narratives. I’ve been there. Give him a chance if you want, but at least go in knowing the odds you face.

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  • Kerrycontrary March 24, 2011, 11:46 pm

    LW 1- it may not be once a cheater, always a cheater…but I’m pretty sure it is “consistently a cheater, always a cheater.”

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  • Jess March 25, 2011, 4:03 am

    I wouldn’t say ONCE a cheater, always a cheater. For instance a few of the guys I’ve had serious relationships have cheating on one or two of their less serious girlfriends before. But all of them have had successful, long term, non cheating relationships too.

    So I do think it’s worrisome that he’s ALWAYS cheated before. To me that just speaks of flawed character. Now, if he never told any of his girlfriends he loved them, or none of them were long term, that is a little different.

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    • Desiree March 25, 2011, 9:04 am

      While I completely agree that romantic relationships are messy (and I therefore do not believe in skewering someone’s character over a few mistakes), I have to take issue with one statement you made. “Now, if he never told any of his girlfriends he loved them, or none of them were long term, that is a little different.” I do not think a history of cheating can be whitewashed by him having never professed love to any of his girlfriends. That seems an odd qualification to make–“oh, he never said he loved them, so it is really not so bad that he decided to stray.”

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    Skyblossom March 25, 2011, 12:17 pm

    Researchers are finding that those who cheat on their partner are self-absorbed and narcissistic. They are able to compartmentalize their feelings including guilt to do what they want at the moment. They tend to think of themself and how they need the affair, deserve the affair and benefit from the affair. They don’t think about their partner. Those who don’t cheat have much higher levels of empathy and so feel the pain that their partner would feel if they cheated and they can’t begin to cheat and create that pain.

    An affair always risks the relationship and so a cheater is a person who is willing to risk the relationship. They also tend to be less invested in the relationship. When someone is very invested emotionally and timewise in a relationship they aren’t willing to risk that inestment but the less invested partner finds it much easier to take the risk since they don’t lose as much.

    So would you like to develop a relationship with someone who is self-absorbed and narcissistic, lacking in empathy and has admitted to repeatedly risking their former relationships with their infidelity?

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  • not leaving my name for this one!!! March 25, 2011, 1:44 pm

    yes once a cheater always a cheater. i would know. i am one.

    I am someone who every time swears up and down to myself I wont cheat agin. I cant help it. Its not from insecurity. I just like the danger in it I guess. Sad I know. If my boyfriend only knew 🙁

    go ahead and dislike this comment but hey, im being honest for the sake of giving blunt advice.

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    • Fairhaired Child March 26, 2011, 3:09 am

      Its actually good to get a different perspective from the other side. Yes, some people may do it for the “thrill of the act” and get turned on more by the possibility of being “caught”. Also some people may do it because of feeling like they dont have “enough” of something in a relationship – either attention or just something missing that they cant place their finger on and they are going to explore until they can find it – but see no reason to leave the current relationship during that said search because everything else is fine.

      I’m not agreeing with the idea of cheating, I’m just pointing out its good to have another view, and that there could be many reasons for cheating. It also seems that a considerable amount of replies have said that they have cheated at least once (I’m also in that category) but feel that it shouldnt label a person and that most of the recognize reasons why the cheating occurred in the first place and dont wish to do it again.

      However most people who regret cheating may not bring it up, unless as a way to say ” you may hear this from so and so but I wanted to tell you first, I have cheated before on ____ girlfriend/boyfriend but now i see how unhealthy it was and why I did it so I wont do it again and plan to be more honest with myself and with you” because they know that it will get around to the new SO. However the LW’s guy friend doesnt necessarily seem to recognize why he cheats or has even tried to make any ways to improve himself/the relationships to prevent himself from “resorting” to cheating.

      I certainly dont go telling any new boyfriend/potential boyfriend “oh ps I cheated years ago because I was unhappy with my relationship and was a spineless girl and instead of breaking up like I should have, I dragged out the relationship and sought comfort in another man’s arms while still dating douchebag #00041A”

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    • TheOtherMe March 26, 2011, 11:08 am

      Thanks for your honesty I.N.L.M.N.F.T.O. but as much as we can’t assume that someone who has never cheated will never cheat, we also can’t assume that anyone who has cheated will keep cheating forever. Everyone is different and contrary to popular belief, people DO change.

      I think that even though you say that you can’t help it, one day there will be someone in your life on whom you will have no desire to cheat. I’m not saying that you’ve never been in love but maybe you’ve been lucky enough to never get caught and maybe one day you will and it will make you see things differently. That “danger” feeling you seek will not be thrilling anymore.

      Have you ever been cheated on ? if so, was it devastating to you ?

      I’m not judging you here, I thumbed you up for your honesty but I also think that each of the other comments have as much merit as yours.

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    • TheOtherMe March 26, 2011, 11:50 am

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