Dear Wendy
Dear Wendy

“I Slept with Someone Else, But We Were on a Break!”

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Guest columnists and contributors are generously sharing their talents and insights while I’m taking some time to care for my new baby. Today’s letter is answered by prolific DW commenter and social media consultant, Sarah Huffman.

My boyfriend and I have been together since my sophomore year of high school. We are both now in college. He’s two years older than I am, so he was a senior when we started dating. Since I was so young when I met him, I felt confused about our relationship because I’d never really been with anyone else. It really bothered me that I was having these thoughts. About six months ago, I decided we should take a break to see other people. He was so pissed about it, I really thought we were done for sure. So while we were broken up I had sex with another guy. We ended up getting back together for my prom. I never told him what I did while we were separated. But I feel if he knew, he never would have gotten back together with me. So, I feel our relationship is a lie now. Should I tell him? — To Tell Or Not To Tell

Unless you traveled back in time to your high school prom six months ago, I’m going to assume you’re freeeesh out of high school and in your first semester of college. The thing about being freeeesh out of high school is that everything still feels like high school. You still have the same perspective of relationships that you did then. So let me clear a few things up for you, being someone who is 2,4,6,7, I DON’T WANT TO TALK ABOUT IT years from high school:

1. It is not wrong to want to break up with somebody because you want to experience dating other people. In fact, realizing you maybe want more experience and having the courage to break up with him and not lead him on is the mature and kind way to go about it.

2. Never, and I mean, never, do the “We’re on a break, not officially a break up” thing. All it does is convey to your partner that you expect him to wait until you’ve had some experience with other people and you might come back to him again afterwards so he should be ready in case. That wouldn’t feel very nice, would it?

If you really and truly told your boyfriend six months ago that you were taking a break to see other people, then you have no reason to feel guilty. The question is, did you honestly tell him you were ending the relationship and planning to see other men? Or did you conceal it and throw out something like “I love you and we’re totally gonna be together forever, I just need some space”? The reason that I’m suspicious this might be the case is your statement, “He was so pissed about it, I really thought we were done for sure.” Um….weren’t you done for sure…..because….you just broke up with him? If you didn’t make it clear that things were done and you were looking around, whether permanently or temporarily, then you may need to own up to that if you feel it’s damaging your relationship.

Now, if you did make it clear that you wanted to date other people, then you didn’t cheat on him, so don’t act like you did. Lying about it or concealing it is just making you feel guilty for something that you made it clear you were planning to do. Hiding stuff because he’s not adult enough to handle it is going to get old, and it looks like it’s starting to already. If you see a future with him and it’s making you feel awful that you haven’t told him everything, plan to be honest with him, whether it comes up naturally later or you feel the need to tell him now. But be ready to accept that he is probably not going to like what he hears.

* Sarah Huffman is a social media consultant who is freelancing art and photography along the way. She lives in Hollywood with her boyfriend, David, and their two cats, Mia and Daphne. She likes spending her free time spying on the neighbors through her window and ruining her boyfriend’s Netflix recommendations by watching bad reality wedding shows and movies starring Sarah Jessica Parker.



74 comments… add one
  • spark November 15, 2011, 7:37 am

    I think it’s clear from the letter that the terms of the break did not contemplate sex with other people. She feels guilty because she knows that he doesn’t believe or expect that she had sex with another boy. I think he deserves to know the truth; it’s apparent that that is a dealbreaker for him, and he is only back in the relationship on the assumption that it didn’t happen. If it was a break up, then she shouldn’t have to tell him. But a dubious “break” probably didn’t open the doors for sex with other people.

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  • theattack November 15, 2011, 7:44 am

    If you actually did break it off with him then you did the right thing. You were also not his at that time, so there’s no reason to tell him (as long as you used condoms and are not putting him at risk for STDs). Your reason for breaking up with him was perfectly fine, and it’s also very common.

    If you were truly broken up with him, this is the classic Ross/ Rachel “We were on a break!” scenario. People will disagree on whether or not what you did was wrong.

    IMO, your bf deserves to know about it if your break up was not clear cut. If it was, then it’s completely up to whether or not you want to tell him. It sounds like you’re feeling pretty guilty here, but don’t hurt him just to clear up your own conscience.

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  • ReginaRey November 15, 2011, 8:18 am

    I want to comment on a particular part of your letter: “Since I was so young when I met him, I felt confused about our relationship because I’d never really been with anyone else. It really bothered me that I was having these thoughts.” LW, it’s OK to feel confused about whether or not your relationship is right for you. It’s OK to wonder what dating someone else might be like, and it’s OK if you don’t think you’ll end up with your high school boyfriend forever. The vast majority of people don’t.

    Are you still having these confused, unsure thoughts? Maybe since getting back together with your boyfriend, you’re happier than ever. But in case that confusion hasn’t gone away, or in case it creeps back in time, know that constant confusion, uncertainty and doubt are signs that a relationship isn’t right. If it scares you to think you’ll never get to experience dating other people, I urge you to not suppress those thoughts. Your late teens and early twenties are about discovering who you are, and in turn discovering what kind of long-term partner might be suitable for you.

    BUT…if you and your boyfriend break up again, it needs to be a complete breakup. No communication, no nothing. Allow yourself to get over him and move on to other people. You could end up together years down the road…but more likely, you’ll grow and mature and find someone even better suited to you.

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  • FireStar November 15, 2011, 8:30 am

    If you broke up with him to see other people… and then you did – then there is no problem. Whether he hoped you would get back together or not – he knew you weren’t together then. I think if the possibility of you being with someone else was so important then he would have asked before you got back together. Why are you feeling guilty? He didn’t think you were together, did he? You don’t have to volunteer any information that has nothing to do with him. (FYI STD exposure does have something to do with him.) Don’t say anything unless asked. And if asked – don’t lie. Tell the truth or tell him it isn’t his business since you weren’t together.

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  • Budj November 15, 2011, 8:49 am

    I would love to tell my hypothetical gf I’m on a break and proceed to bang a different girl every 3 months during said scheduled breaks while I “sort things out”. I could have my cake and eat it then too.

    Taking a break to sort yourself out wasn’t wrong….going out on a couple dates with a couple different guys while you are on a break isn’t wrong…afterall that’s why you wanted the break…but screwing a dude while you are “on a break” and not “broken up” is messed up. If you don’t tell him and air it out I think that this will just be an indefinite festering egg in the nest of your relationship.

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    • Budj November 15, 2011, 8:50 am

      for the record I hate that phrase I used above…because I don’t quite understand why someone wouldn’t want to eat the cake they bought…but you get the point.

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      • MissDre November 15, 2011, 9:04 am

        Ha! I always thought that too… what’s the point of having cake if you CAN’T eat it? Strange expression…

      • oppositeofzen November 15, 2011, 9:38 am

        That phrase made me wonder too. I heard the other day that it means that you can’t eat the cake and expect that exact same cake to still be there on your plate when your done. I wish I had a constant piece of cake…

      • lets_be_honest November 15, 2011, 9:49 am

        You’re right. I just looked it up out of curiousity. Apparently the original wording was more like “you can’t eat your cake and then have it still.” Stupid.

      • 6napkinburger November 15, 2011, 10:52 am

        I think linguistics is/are(?) super interesting and I love that this is an example of “and” being used to denote chronology rather than conjunction. In conjunctions, it shouldn’t matter which comes first, but when it is used to express a linear progression, clearly it does. “Wash and fold” is another example.

        I wish I could go to school and just study all the things I find fascinating. Maybe a rich Aussie will awkwardly proposition me, so that can finally be my reality.

      • Budj November 15, 2011, 10:57 am

        I just got the joke at the end, bravo.

      • lk November 15, 2011, 1:55 pm

        Me too…. I recently realized that the height of my ambitions is to sit in a pile of blankets blasting dubstep music, eating dark chocolate & reading everything ever written while a devilishly handsome poet rubs my neck & feet.

      • Britannia November 15, 2011, 5:03 pm

        Um… wow. Sign me up for that!

      • Budj November 15, 2011, 10:13 am

        haha – that makes so much more sense….but the amount of words in it makes me not want to type it that way.

  • Carolynasaurus November 15, 2011, 9:01 am

    Ok, I know I say a lot that I think I know what’s going on, but I do this time! I was a sophomore when I started dating my first boyfriend, a senior.

    Let me ask you one question because I think I know where this is going. Did you break up with him purely to date other men or was it to experience single life after being in a relationship for so long at so young?

    If it’s the latter, the problem will get much worse before it gets better. I have to imagine that if things were great with this guy right now, you wouldn’t think twice about keeping this secret (whether or not it’s something you should feel guilty about isn’t a question I can answer) for the sake of your relationship. You wouldn’t risk ruining it if there were no way he could ever find out about it. So either it’s about to come out from someone else or you’re about to unleash it because you aren’t happy.Think long and hard about that before you decide whether to tell him because if you aren’t happy, don’t tell and just end things.

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  • Jess of CityGirlsWorld.com November 15, 2011, 9:05 am

    I’d just like to make a request that LWs please be more specific about timelines and years together rather than refer to life phases by college and high school. It’s not that there is a problem with using your education as a marker for time but some writers assume we know how long ago that was. To say you met someone or dated someone “way back in high school” doesn’t tell me much. In today’s case, it looks like that might have been 6 months. For others, it could be 6 or 16 years. If you don’t tell us your age or the number of years, its meaningless data.

    Though, to build on what Sarah says, I find that the longer you are out of high school/college, the less often you need to measure your life against it.

    As for LW’s question…. leave the past in the past. There is no need now to bring this up, in my opinion. But a better question is, what did you learn from this experience? Are you happy in your relationship now? Did the experimentation demonstrate that you really DO want to be with your boyfriend for the forseeable future? Or did it whet your appetite for playing the field? Hopefully you’ve given some heavy thought to those questions.

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    • MissDre November 15, 2011, 9:47 am

      Your last paragraph is exactly what she needs to hear and think about. What did you learn from this? Now think about what you really want? Honestly LW, you have a lot of growing up to do and I don’t mean that in a condesending way. I just mean that you will have A LOT of experiences in the next few years that will change you and shape you. Take this as an opportunity to learn about yourself and what you want!

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    • 6napkinburger November 15, 2011, 1:54 pm

      Can we have a mini discussion on generations? Sometimes I think that would make things easier, if we knew what “generation” they were in.

      Is generation Y and the “millenials” the same thing?
      What generation is this LW? I think its younger than a millenial, right?

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    • Nadine November 15, 2011, 5:53 pm

      Also, for not-Americans…. I’ve never really grasped what “sophomore” is. Is it the middle years? How old are you at this point??

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      • 6napkinburger November 15, 2011, 6:06 pm

        It’s the second year of anything. It goes: Freshman, Sophmore, Junior, Senior. They are both adjectives to describe which “year” you are, and nouns, as in, you are a sophmore.

      • 6napkinburger November 15, 2011, 6:09 pm

        If you follow the “typical path”, in high school, you are:
        Sophmore: 15-16
        Junior: 16-17
        Senior: 17-18

        College just continues:
        Freshman: 18-19
        Sophmore: 19-20
        Junior: 20-21
        Senior: 21-22

        Of course, not everyone does it on this timetable, but it is “typical.”

      • Nadine November 17, 2011, 4:51 pm

        Thank you so much! All the American things I’ve read in the past will now make a bit more sense. I never got the junior thing, it made no sense that being Junior seemed to not really be that junior….? IN NZ its just Years, like Year0ne through Year Thirteen….

  • GatorGirl November 15, 2011, 9:14 am

    Personally, I think you should just end the relationship now. You say you feel like you’re living a lie…so what’s the point? Get yourself checked for STD’s and if anything comes up that should be relayed to your BF, otherwise just keep it to yourself – it’s not going to do any good to bring it up now. So break up, get tested, and grow up.

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    • Theenemyofmyenemyisagrilledcheesesandwich November 15, 2011, 12:34 pm

      You know, not everyone (or anyone) who has sex with more than one person needs to be treated as if they are dirty. I personally don’t think she made the best decision, but “So break up, get tested, and grow up” seems really harsh.

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      • GatorGirl November 15, 2011, 12:57 pm

        It sounds a little harsh, I agree, but I stand by it. LW identies her relationship as “living a lie” – so they should break up. The LW has identified herself as just out of high school (based of of her comment “got back together for prom six months ago”) and there is a lot of growing up that needs to be done during the transition from high school to college. I also beleive you should be tested for STDs between every sexual partner – no matter how careful you were.

        My intent was not to vilify the LW or make her feel dirty (we’ve all made our share of mistakes). But I do think she needs to move on from this relationship, make sure she has her health, and grow up a little.

      • theattack November 15, 2011, 2:24 pm

        So she’s not allowed to date around while she’s growing up? These experiences are what people learn from. If she avoids these situations entirely until she has all the answers, she’ll be a late 20 something wanting to settle down with no relationship skills.

      • GatorGirl November 15, 2011, 3:12 pm

        I’m not sure how you got “not allowed to date around.” I’m 100% advocating for the LW to end this relationship and move on. Moving on would include exploring other relationship options – or not dating at all, what ever the LW chose.

      • theattack November 15, 2011, 5:11 pm

        Guess I misinterpreted what you were saying from this: “The LW has identified herself as just out of high school (based of of her comment “got back together for prom six months ago”) and there is a lot of growing up that needs to be done during the transition from high school to college.”

        There’s always a bad attitude toward young people having steady partners or serious relationships here, and the advice is so frequently “Don’t worry about it now because you’re too young to be in a LTR anyway.” That advice irritates me beyond anger usually, so maybe I was just being overly sensitive and misunderstood you.

      • GatorGirl November 16, 2011, 9:41 am

        I can see that. But I’m not one to slam LTR for younger people. My first BF lasted 3 years from my sophmore to senoir year of high school. But I had a lot of growing up to do between high school and college, which is what sparked my comment. I lived in an idealistic world in high school and the real world is very different.

    • CatsMeow November 15, 2011, 3:42 pm

      Getting tested for STDs is a healthy and responsible thing to do. I wish people didn’t jump to the conclusion that one must be “dirty” to need a test, or that the suggestion of testing implies dirtiness.

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      • SpyGlassez November 15, 2011, 4:23 pm

        Anyone and everyone should get tested between partners. It doesn’t matter if it is two or twenty. No one wants to be that LW writing into DW: “Help, I think I have an STD but I’m afraid to get tested because I don’t want my BF to know.” There’s nothing slut-shaming about it. For instance – I know about one of the gals that the Ginger was with before me. She was not very sexually active, but she got tested whenever she moved into a different LTR. That was her way of remaining healthy and safe. Plus, most STDs are much easier to deal with when caught early.

      • GatorGirl November 15, 2011, 4:24 pm

        Thank you! There was a chart in my college’s health center- it showed how if you had sex with one person, you had sex with all their partners. It was similar to this link. It is better to be safe then sorry, or dead.

      • Budj November 15, 2011, 4:29 pm

        That reminds me of the game my swim team in college used to play. We had a “web” diagram that showed how everyone was connected on the team. Pretty gross when you looked at it as a whole – fortunately I only had a couple lines to me.

      • Theenemyofmyenemyisagrilledcheesesandwich November 15, 2011, 5:27 pm

        I don’t disagree that one should get tested between each partner…Not at all. I’m also not implying that one needs to be dirty to get tested. I just think that there IS a subtle undertone of slut-shaming concerning responses to this letter.

  • DDL November 15, 2011, 9:28 am

    If he asks, tell him. Say “we were on a break, and I told you I wanted to see other people”. Just don’t be surprised if he tells you he’s slept around too.

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  • silver_dragon_girl November 15, 2011, 10:07 am

    This is why I loathe the phrase “take a break.” It’s such a cop-out. If it’s longer than, say, three days, just call a spade a spade and officially break up. It avoids confusion all the way around.

    Anyway, LW, you probably don’t want my advice. I would tell him, because I have a horrible guilty conscience and I would have to get it off my chest if I felt even the least bit unsure about it. BUT I recognize that most people aren’t like that. You were broken up for 6 months…at what point did you sleep with the other guy? If it was right after you broke up or right before you got back together (like, if you were already talking about starting things up again) then I think it was kind of a shitty thing to do. BUT, hey, 6 months is a long time. And who’s to say he wasn’t out gallivanting with other women, too?

    If you feel guilty about it, it’s probably because you know it would bother him. So the question is, which is worse: Your guilty conscience, your boyfriend finding out at a future point from someone else, or the possibility that he will break up with you for good if you tell him?

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    • Budj November 15, 2011, 10:15 am

      Another good point – I totally didn’t see that it was a 6 month break! Holy crap…cop out indeed.

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    • Sarah November 15, 2011, 10:21 am

      I think it was they broke up six months ago, but got back together in time for prom. So at the very earliest, they could have broken up in May and gotten back together early June (Kids still have Prom and Graduation in June right? Get off my lawn!). So I think we’re talking about a few weeks here, maybe even less. The high school–>College–>wtf highschool again–??? thing messed my brain up when I first read it. What I’m hoping didn’t happen was that the LW saw a hot guy other than her bf, dumped him for a day, slept with the other dude that night and the next morning patched things up again. So I’m giving her the benefit of the doubt that she had a few weeks to be ” on a break”. Btw, how are people getting laid in highschool? Guys never talked to me like that in highschool, I was too busy listening to Harry Potter on cd and wearing braces til college :/.

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      • silver_dragon_girl November 15, 2011, 10:47 am

        Oh dear, ok, reading it that way, you’re right…a very short break indeed…
        And also, I agree on the “how are kids getting laid in high school?” bit. I couldn’t make eye contact with cute boys until I was like 20.

      • ReginaRey November 15, 2011, 10:50 am

        For real! I didn’t get kissed until I was 16…by this troll looking dude who basically face-attacked me. And it wasn’t until I was 18 and in college with my first boyfriend that I even touched a P, or allowed it near my V. I don’t know how kids get it on in high school…I was terrified of my own inexperience, and of my parents.

      • princess bananahammock November 15, 2011, 11:12 am

        LOL at “face-attacked.” My friends and I call that the “Blitzkrieg.”

      • rangerchic November 15, 2011, 11:28 am

        My oldest daughter is in high school and she has a friend who is constantly having sex with her boyfriend (all are juniors). I only know because my daughter told me because she is pissed at her friend for not wanting to spend time with her anymore…it is all about the boy. Anyway, I’ll tell you where they have sex….ready??? At the high school! I know because they were caught and arrested for indecent exposure or something like that. Otherwise they go off on “walks”. Come on parents – get real!!

      • FireStar November 15, 2011, 1:52 pm

        I have a friend who is a teacher in high school – and I could NOT BELIEVE what children were involved in. He would go away to sports meets for track and would spend the night constantly herding kids back to their room, breaking up interludes and shutting down strip shows etc. And these were supposed to be the “good kids”. It made me understand the parents that home school.

      • Budj November 15, 2011, 1:57 pm

        My little brother get a bj in a dark hallway during after school activities when he was in high school. It’s pretty easy.

      • TaraMonster November 15, 2011, 11:35 am

        Hahaaha! I love when people say P and V. It just cracks me up, and I’m not sure why. Also, I don’t know how no one has said this yet, but I just keep thinking: WE WERE ON A BREAK!!

        Lol. I’m amusing myself this morning.

      • CatsMeow November 15, 2011, 3:44 pm

        You sound just like me! I can’t remember if I was 16 or 17 when I also had the sneak attack thing happen to me as my FIRST kiss! And he was very troll-like in appearance.

      • AKchic November 15, 2011, 12:26 pm


        It’s not all that hard to get laid in high school. Or junior high. Or elementary school if you want to get real squicky about it.

        Remember – sex in itself doesn’t take all that long, and kids are inventive.

      • GatorGirl November 15, 2011, 1:03 pm

        I think the “getting laid in high school” depends on the community. Neither myself or my friends had any problem getting laid. Our health center even gave out condoms and drove us to Planned Parenthood to get birth control. And trust me…we were not the popular girls (I had a Blues Clues hoodie I wore on a regular basis). I should note we went to a private boarding school in Pennsylvania. Maybe boarding school kids get it on more?

      • bittergaymark November 15, 2011, 1:08 pm

        Of course it’s incredibly difficult to get laid in high school. If it wasn’t we’d probably have a real problem with unwanted teen pregnancy — oh, wait… We do.

      • Britannia November 15, 2011, 1:13 pm

        It’s really, really super easy to have sex in boarding school. I went to a small one for my freshman year of high school after being expelled from a public school, and there were literally only TWO kids who DIDN’T have sex. Everyone else was sexually active.

        In public school, there’s more virgins, but it also isn’t very hard to get laid. Where there’s a will, there’s a way.

  • TheOtherMe November 15, 2011, 10:47 am

    I would tell him. It might be the end of your relationship but the guilt will probably lead you there anyway. If you’re honest, it might save the relationship.

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  • AKchic November 15, 2011, 12:24 pm

    A break with “conditions” is not a real break. Period. It’s just backing off but still in a relationship.
    If you were in a real break, then whatever you did with other people is your business. As long as you used protection, it’s your business. I advocate for “what he doesn’t know won’t hurt him”. Only because of the fact that you wrote:
    ” I decided we should take a break to see other people. He was so pissed about it, I really thought we were done for sure.”
    To me, combined with the age difference, I have to wonder if maybe he’s a bit controlling to begin with. Maybe acting like the one in charge because he’s “older” and “more experienced”. Were it me, I’d want a longer break to get more experience. If it’s meant to be, you guys will end up together in the end.

    Of course, this isn’t my life. If you love him, then stay with him. Don’t tell him because honestly, it sounds like it will cause too much trouble. You have nothing to feel guilty about, and that sounds like the problem – you have a guilty conscience.

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  • LSS86 November 15, 2011, 12:36 pm

    I re-read the letter, and now I’m confused. You say that you wanted to take a break to see other people. Then you say that he was so pissed, you thought you wouldn’t get back together. And then you write, “so while we were broken up I had sex with another guy,” which to me indicates that the only reason you slept with someone else is because you thought you weren’t going to get back together. But you said the whole point of the break was so you could see other people. I guess I just don’t understand what you were expecting out of the situation.

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    • AKchic November 15, 2011, 12:45 pm

      To me, I have to think that the LW is still in high school. That right there is indicative of some level of immaturity with relationships in general and NOT ready for sexual relationships. I’m sorry, but 16-17 year olds don’t need to console themselves with sex at the loss of a relationship when they were trying to have a “temporary break” in the first place to be able to see new people.

      If Prom was this last spring for her, then she is probably 17 (or thereabouts). Juniors have proms, right? I dropped out my freshman year, so I have no clue about dances or anything like that. I went to one, and I was forced to go. A Homecoming dance at the beginning of my freshman year. My mom forced me to go because SHE was going (it was her high school too). I got stoned prior to my arrival, punched out one of the football players in the Homecoming “court” during the event (he deserved it, trust me) and spent most of the night hanging out outside of the actual event.

      Either way, this girl is not mature enough for sexual relations with multiple people, probably not even emotionally mature enough to handle the one relationship she is in now, all because of the sexual component.

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      • bittergaymark November 15, 2011, 12:49 pm

        She, uh, specifically states they are BOTH in college now…

      • LSS86 November 15, 2011, 12:49 pm

        She says they’re both in college now. But I don’t know of any colleges that have “proms.” Dances, sure, formals, yea, but proms? The whole letter is just very confused to me.

      • Morgan November 15, 2011, 12:57 pm

        I think she’s a freshman in college now, and all this business went down about 6 months ago, the spring of her senior year of high school.

      • bittergaymark November 15, 2011, 1:04 pm

        Honestly, of all the letters on here, this one was one of the most clear timelines to sort out. No, seriously. She gives clear specifics, nothing contradicts, and six month ago would be May which is when prom often is…

      • LSS86 November 15, 2011, 4:39 pm

        Yea, I just read it yet again and I think I get it. I was just confused because all this must have happened several months ago at this point. My first couple readings assumed that she was writing this soon after getting back together with her bf (and colleges have dances at all times of the year, so I figured a beginning of the year dance… I don’t know, I was rationalizing it!) If it was her high school prom, then she’s been sitting on this for 4 months and just now decided to write in? It makes a big difference when you confess something to your boyfriend. Telling him that you slept with someone else while you were on break soon after you get back together makes sense, but to tell him out of the blue 4 months later? That’s going to be a very different situation.

      • AKchic November 15, 2011, 1:28 pm

        Proving my point that I know nothing about high school dances.

    • LSS86 November 15, 2011, 12:47 pm

      Anyway, I think if you seriously see a future with this guy, you should tell him. If not, break up with him now while you still have time to enjoy college. If you’re feeling the urge to date/sleep with other people, there’s no better (read: easier) time to do that than college.

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  • bittergaymark November 15, 2011, 12:40 pm

    Eh, move on already. No, seriously. Move on. This is all so very high school. Moreover you never even bother to say it’s a great relationship now — that you really love him — or even that you really care about him. And from your actions you sure don’t seem THAT into him. It sounds more like things didn’t work out with man # 2 and suddenly you found yourself alone and needing a date to the really big dance… Hey, don’t beat yourself up about this though. Nobody, and I mean, NOBODY I know is still with the very first guy they ever dated back in high school.

    PS — Plus I am sure he was monk like during your “break.” College guys are notoriously big fans of monogamy — especially when getting mixed signals from their girlfriends…

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    • Christina November 15, 2011, 1:25 pm

      Thanks for saying that BGM. If you were dating during the break, then Dude was dating during the break. Especially if you initiated the break. There’s no need to tell him anything that happened and there’s no need to tell him about the other guy and cause another break-up.

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    • lk November 15, 2011, 2:00 pm

      “College guys are notoriously big fans of monogamy — especially when getting mixed signals from their girlfriends…”


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      • Fabelle November 15, 2011, 2:10 pm

        Yeah, if she wants to feel less guilty then all she has to do is assume that he’s also fooled around during their “break”. Then she can obsess wondering if he did or didn’t, and she’ll have a new problem!

        I agree that she should probably just move on from the relationship, but if she doesn’t want to, then she needs to just stop feeling like she’s “living a lie” & get over feeling guilty.

    • theattack November 15, 2011, 2:55 pm

      I’m not _still_ dating my high school boyfriend, but I am dating him AGAIN after a situation very similar to the LW’s. It can be done. Several years after the drama, we’re talking about getting married. There’s no reason that sort of thing can’t work out.

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      • SpyGlassez November 15, 2011, 4:27 pm

        Key point, I believe, being “several years” and dating AGAIN.

        Not that I’m attacking you, but I think that corresponds with what BGM is saying.

      • theattack November 15, 2011, 5:08 pm

        You’re right, those two factors are what has made this thing work with us. I didn’t really see BGM say anything about the potential to work out in the future, so I just wanted to throw that possibility out there. The LW really didn’t mention any inherent problems in their relationship. The problems are things that come from being young and inexperienced.

        There aren’t always second chances with another person, but sometimes there are. LW, if you were having the need to get out and explore other people just six months ago, I’m wondering if you were actually able to fully get that out of your system before you jumped back into this relationship. You may really want this relationship to work out, but until you actually get to roll around in the grass some, you’ll always be looking over the fence pining to get over there. You will either be miserable or cheating. When I tried to do what you’re doing, I ended up being both. Take care of your curious urges for now and just hope that he’ll be around later. I say this as someone who hates the general vibe of “break things off right away” that’s here so often on DW, but you really cannot continue this relationship in a healthy way until you settle the other stuff. You may not get another chance, but that’s probably better than potentially being miserable forever.

    • CatsMeow November 15, 2011, 3:52 pm

      Yeah, I think she should be single too. It’s hard to break it off (for good) with your first love. I remember feeling like I might not ever find someone else as good as my first boyfriend, or someone who loved me as much. But now, I can’t imagine being WITH him (not that there’s anything wrong with him – but we grew in different directions). You live and learn. 🙂

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    • AKchic November 15, 2011, 4:53 pm

      Mark – I agree with you. I think that she needs to be on her own. She doesn’t seem mature enough for a LTR at the moment. She needs to figure herself out and get over her guilt complex over what seems like a one-night (or day)-stand while in high school when the two of them weren’t even together at the time.

      People change as they age, and some couples do not change together. Not in this day and age, not in our society.

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  • Meredith November 15, 2011, 8:56 pm

    BUT WE WERE ON A BREAK!!! Did anyone else watch Friends besides me? Lol. I don’t think you should tell him.

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  • NerdyArtGirl November 16, 2011, 12:37 am

    I might be reading this wrong but maybe you just want out of the relationship. That’s the feeling I get from this letter. You wanting to “take a break” and sleeping with someone else ( knowing that if he found out, he might break up with you ) might just be an attempt on your part to end it. You want him to find out so he can break up with you and than you don’t have to be the strong one and end it yourself. You just don’t want to admit to yourself and to him that you are not happy and don’t want to date him anymore.
    To me this letter screams ” I want out!”
    So get out. Break up with him. Move on. And no point in telling him about sleeping with someone else.

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  • Travis Walken November 28, 2012, 1:32 am

    She said that if he knew then he “definitley wouldn’t have gotten back together”…so by not telling him she is taking away his ability to make an informed decision about his future, and how does she know that he “definitely wouldn’t have gotten back together” unless he had said something to put her on notice of what he considers important to his decision?

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  • rrr April 14, 2017, 3:13 am

    This is exactly why I recommend treating any break/break-up/whatever as final and never come back. Having abundance mentality guarantees you’re not missing out on anything, because there’s enough people in the world you could get in a relationship with.

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