“I Work With My Boyfriend and Someone He Used to Hook Up With”

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My boyfriend and I have worked together for several months now, but we only started dating recently. He says that he has liked me ever since we first met when he got hired, and to his credit I didn’t really do anything to encourage his advances (I’m very shy), so he ended up hooking up a couple times with another girl we work with. When he and I started seeing each other (casually at first) he broke it off with her immediately even though she liked him and wanted to make them a “thing.” Shortly after that, we became exclusive and “came out” at work about our relationship.

The issue is that he still remains close friends with the girl he slept with before me, and it is clear she still has feelings for him. It’s also kind of painful for me to have to see her every day knowing that they had a physical relationship and maintain a close emotional one. She texts him all the time asking him to hang out and she is very flirtatious with him at work. A few weeks ago they went out for drinks after work, and he told me she asked him “what happened with them” and was talking about how she thinks they connect, which I think is a really inappropriate thing to ask someone who has a girlfriend. Clearly what happened is he got a girlfriend, but I don’t get the feeling she respects that.

When I brought up my concerns about her to my boyfriend, he was really understanding but didn’t seem to believe she still likes him. I don’t want to ask him to stop being friends with her, as he clearly values her friendship (not to mention he moved to this city recently and doesn’t have a lot of friends) and has no interest in her romantically, but it bothers the fucking hell out of me. He says he picked me over her, that he loves me, and that I am a very important person to him, all of which I know is true, but I just can’t get over his friendship with her. I don’t know if the problem lies with me, if I just need to make peace with it and move on, or if maybe there is a part of him that enjoys the attention she gives him. Is it reasonable for me to ask him to stop being friends with her? — Work Love Triangle

No, it isn’t reasonable for you to ask your boyfriend to stop being friends with anyone, especially considering you’ve been dating, what, a few weeks? I mean, I wouldn’t even ask my husband of 5-1/2 years to stop being friends with someone, even if it was someone I knew he’d slept with and whom I believed might still have feelings for him. What I would do is make it very clear how uncomfortable I was with his being friends with someone who had so little respect for me and our marriage, and I would ask what he planned to do to help make me more comfortable with their friendship. I would suggest you do the same, framing your discomfort not as jealousy but rather as concern that this other woman doesn’t seem to understand or respect his relationship with you. HE may know you’re the one he picked and YOU may know that, but it seems that this other woman still thinks she has a chance and that she is much more interested in a romantic relationship with your new boyfriend than in a platonic friendship.

I don’t think it’s reasonable or appropriate that you ask your boyfriend to stop being friends with this woman, but I absolutely think it’s reasonable to suggest you be included in their get-togethers (drinks after work, etc.) until you feel more comfortable that this woman understands and respects your relationship and position in your boyfriend’s life and until YOU understand and respect HER position in your boyfriend’s life as a platonic friend/colleague who is no longer harboring a desire for a romantic relationship. If comfort and mutual understanding can’t be established across the board in, say, a month or six weeks (at which time, one would hope that, if this other woman only wanted to date your boyfriend, she would have given up), you might want to consider moving on since it would then seem that a conflict of interest was impeding the success of your relationship.

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If you have a relationship/dating question I can help answer, you can send me your letters at wendy@dearwendy.com.

43 Comments

  1. So I have a similar problem with my boyfriend of 7 months and a girl at work. They never dated but have always been friends, and she is also in a relationship with a guy she sees herself marrying. However, she gets mad if my boyfriend and I go shopping together because that’s “their thing”. She eventually started to give the silent treatment, and he had multiple conversations with her about how she should be nicer to me. Nothing really changed. Recently my boyfriend told her he wasn’t comfortable with her calling him “her husband” (this was not my concern since a lot of people have “work wives”). She kind of freaked out and sent me a long text about how they are getting divorced because of me, and how I’m insecure because I will never be as good as her. Then she texted my boyfriend that she can’t help it he thinks he likes me when really he cares more about her because she’s so much better, and that she will be waiting for him for when we break up. I am just ignoring her for the time being, but I honestly don’t think I can keep dating mu boyfriend if he stays friends with someone who is disrespectful to me. Sorry that’s not anything helpful…

    1. Wow WHAT THE FUCK. sorry this is happening. Like, Iit’s understandable (though obviously shitty) when someone has a thing for their friend and keeps flirting despite the fact that the friend is taken, but it’s totally totally batshit that she’s saying shit to *you*. (And the things she’s saying are insane also…)

      1. Thanks, everyone in the office thinks I’m this crazy bitch that’s overreacting. It’s always good to have DW to remind me of what’s normal.

      2. Avatar photo muchachaenlaventana says:

        yeah this is not normal at all. I cannot believe she would text you that shit and people think you are the crazy one?? Did you show your bf the texts? I am sorry you are dealing with this, it would be hard for me to date someone who ignored a friend of his treating me that way.

    2. Avatar photo Dear Wendy says:

      Whhhha? That shit’s crazy!

    3. Fortunately my boyfriend has no desire to be friends with her anymore. He feels she would act the same way if he dated anyone, which is a shitty thing to so as a friend.

      The crazy thing is that I’m the one who slept with a different coworker a few months before we started dating. It has never been an issue, and when we started dating my old hookup guy had a heart to heart with my boyfriend about how happy he was for us. Ah the highs and lows of an office filled with people under 30.

    4. Avatar photo Moneypenny says:

      Um yeah, that is SO weird!!

    5. I haven’t read everything, but wow. She’s a fucking lunatic.

    6. jilliebean says:

      They are getting “divorced” because of you? Wow that’s realllllly crazy talk!!!!

  2. I’m loving all of Wendy’s advice this week. I just am. That is all.

    1. Avatar photo Dear Wendy says:

      Aw, thank you! I need a tiny ktfran to keep in my pocket for days when I’m feeling less-than-confident or like I can’t do or say anything right. You always make me feel good.

      1. RedRoverRedRover says:

        I read that as “I need a tiny kitten in my pocket” and I was like, WHO DOESN’T?!?!

      2. Avatar photo Moneypenny says:

        I concur!!!

      3. You’re welcome. It’s true! And that makes me super happy that I help brighten someone’s day!!!!
        .
        We should market this. A tiny affirmation box to fit in one’s pocket. Customized of course.

  3. Laura Hope says:

    He knows how she feels and probably enjoys the attention. But I wouldn’t assume it’s anything more than that. He chose you.
    Now you could get crazy possessive and break up the friendship but what does that say about you? It says insecure, controlling person who doesn’t treat her (brand new) boyfriend with respect. He might run for the hills.
    So here’s what I would do. Take a deep breath, loosen my grip and let it unfold. You’ll find out if he’s worthy of your trust in time.

    1. Skyblossom says:

      Most workplace affairs begin as friendships that deepen into romantic feelings. Many of those people weren’t intending to have an affair so it is best if he doesn’t put himself into a compromising position. It is fine to remain friends, like Wendy said, but he needs to establish firm boundaries that protect his relationship. So while it is ok to talk to the friend he should walk away if she begins to flirt. He needs to make it obvious that their friendship is only a friendship and that the past will remain the past, there is no romantic future. He should take his girlfriend along if he goes out with the friend after work. The friend may need to see them interacting as a couple repeatedly before she is ready to move on. He should probably limit the number of texts to the friend and not respond to any that are flirtatious.

      1. Stillrunning says:

        Good advice and well said.

  4. Cleopatra Jones says:

    WWS.
    IMO, so much of the angst that I feel when I read this letter seems misdirected to me. You seem to be pointing the finger at the other woman because she does not respect your relationship. She really doesn’t have too because she’s free to like your boyfriend to her heart’s content.
    .
    The problem is your boyfriend doesn’t respect your relationship. He’s the one you should who’s letting you be uncomfortable because he hasn’t set clear boundaries with the other woman (and that’s what she is). I feel like he’s saying the words (you’re important, he liked you for a long time, etc.) but his actions don’t match his words (going out for drinks where they talk about their former relationship, not curtailing her flirtations with him).
    .
    If it were me, I would have a talk with my boyfriend where I expressed all of my concerns about his former relationship. Then I would see if the situation changed where I felt comfortable, if not then I would move on.

    1. Skyblossom says:

      I think we were typing our thoughts at the same time, with the same idea! I must say I agree with you.

    2. Avatar photo Moneypenny says:

      Yes to all of this. You said it better than I could. And I’ve totally been in this same place and wish I’d handled it the way you described!

  5. Avatar photo kmentothat says:

    I feel like people here have been edging a little too far into “cool girl” territory where you can never ever express discomfort with your significant other’s relationship with a person of the opposite sex or you’ll be the “crazy” girl. There was a recent thread that I saw that get thrown around a lot. I think just as it’s wrong to throw the blanket statement that men and women can’t be just friends it equally wrong to say you can’t ever ask your significant other to stop being friends with someone. I think you have to evaluate the situation and do what you think is best, and your significant other has the right to react and do what they think is best. Here’s what I see:

    1. Look, a guy who hooked up with one coworker and started dating another within a few months at a new job doesn’t sound like someone with rock solid judgment. Wouldn’t be my first choice.
    2. He has known you both for a short period of time (months). I think when it’s not a deep, long-standing friendship that existed before you and would exist after you, that’s very different than a pretty new friendship.
    3. You say he doesn’t have many friends. If LW was this guy, I bet we’d all be encouraging him to make more friends, join more activities, etc. just for his own well-being. Seems like he’s focused more on sexual and romantic relationships.
    4. If it was a friend where the hook up happened in the distant past and they’ve had time to readjust to platonic it’s one thing. A few months before is still pretty recent.
    5. I think well-intentioned friends of the opposite gender that have direct access to you will make an effort to be friendly if not friends with you and go out of their way to make it clear they are totally platonic. I have a number of guy friends, and when they get girlfriends I understand that the dynamic may change a bit, but I make it a priority to include the gf and do what it takes to make her feel at ease. More times than not I become friends with them (because my guy friends are awesome so they people they date are usually awesome too). I have rarely had any guy friend’s gf be jealous of me. So put me in the camp of this girl is still holding a candle for him, because she hasn’t shown any attempt.

    If I were you, I’d tell him if she’s an important friend to him, you really want to get to know her better and find a way to establish boundaries that respect your relationship. If he and she aren’t willing to do as Wendy suggested and make an effort to make things very above board…is it really worth the drama in your place of work? The place that pays your bills?

    1. Avatar photo muchachaenlaventana says:

      Yes the whole Cool Girl TM gets a bit old after awhile, I will agree. I think its one thing to ask your boyfriend patently to drop a friendship, and another to ask him to maybe not pursue a friendship or continue a new friendship if the situation like the one above has presented itself. If there is a friend that clearly has no respect for your partner or your relationship, that is just not cool.

    2. Avatar photo something random says:

      In general I think you make some good points. In Kare’s situation the friend is downright rude and obnoxious. If a “friend” is abusive and toxic I think that is a category all of it’s own. But generally I do think is controlling to demand a friendship be terminated. I’m no expert but it seems most people would be able to negotiate some boundaries that allow concerns to be addressed while personal autonomy is respected (because each person trusts the other’s judgement and commitment to the relationship at the end of the day).

      In the lw writer’s case, the friend really didn’t do anything wrong (I think flirting is subjective) until she initiated the questions about “what happen” and that they “connect”. Even this isn’t that wrong. After all, the lw and her boyfriend only started dating very recently. So maybe the friend does still have feelings and was checking things out to see if things had gotten serious. I don’t think that justifies asking the boyfriend to shun the lady. Clearly the boyfriend was uncomfortable with the conversation and shut down if he came right back and told the letter writer all about it.

      I think you and I both agree with Wendy’s advice about making an effort to establish some comfort and boundaries around this fellow colleague. I think the timeline sounds good, too. Basically, WWS.

      1. RedRoverRedRover says:

        I agree, I don’t think it’s being a “cool girl” to say that you don’t get to tell your partner to stop hanging out with someone. You don’t. What you do get to do is tell your partner how you feel about it, and control how you react to it. How your partner reacts to that is their own choice, and if they react in a way that you’re totally uncomfortable with, then that’s when you re-evaluate whether they’re the kind of person that you want to be in a relationship with.

      2. I was the “cool girl” once and tried to ignore a girl who was friends with my ex-boyfriend. She was in love with him and wasn’t friendly to me, but I didn’t speak up for the sake of not wanting to be the “jealous girlfriend”. Now they are engaged, and I am more honest to the guys I date if I feel something is disrespectful to our relationship. (And that girl was a saint compared to the girl I’m dealing with at work.)

      3. RedRoverRedRover says:

        Yeah, I think you’ve realized that there’s something in between “cool girl” and “jealous girlfriend”, which is the point I was trying to make. You don’t have to pretend to be ok with it, you can talk to your partner and work something out. But you don’t get to mandate that they stop talking to the person. We saw a LW in the forum recently who did that, and all it did is escalate the behaviour.

      4. Avatar photo kmentothat says:

        I think there is something in between, but I think the LW in forum got bashed unfairly. Her bf was really a cad and should she have asked for a absolute cut off for the friendship? Maybe not, but if my boyfriend had a friendship with a female he hid from me I’d probably react not great either. Everyone on the thread kept saying because she freaked out that’s why he went behind her back and escalated into multiple hour phone calls everyday, constant texts, lies, etc. It’s a bit like saying because she didn’t sleep with him enough that’s why he cheated. His behavior escalated because he decided to escalate. She wasn’t to blame for his actions, she was to blame for hers. But a lot of people called her “crazy.”

      5. RedRoverRedRover says:

        To be fair, I think the people who said “crazy” weren’t saying that because she told him to drop the friendship, but because she called the other woman up and went nuts on her. I understand the urge to do that, but come on. That’s not normal behaviour to actually do it.

      6. RedRoverRedRover says:

        To be fair, I think the only thing people said was “crazy” was the way she called up the other woman and went nuts on her over the phone. No one thought she was crazy for thinking her husband was engaging in extremely inappropriate behaviour.

      7. Avatar photo something random says:

        Its funny how different circumstances and nuances change the direction of the advice given to letter writers dealing with similar themes. Sometimes I catch myself changing the tune I would normally have because of a position I took on a separate letter. Then I try to examine what clues I have to justify my inferences. It just reminds me of how little we really know about things when we give out all this helpful advice. I’m glad Wendy is so good at it and I get to be flawed, side-taking, commenter. 🙂

      8. Avatar photo something random says:

        Honestly though, if you had spoken up do you think you and that other guy would still be together and that “friend” would be long gone? I actually think its very healthy to be able to talk about your feelings with your partner, even and maybe especially when those feelings are less than pretty. It fosters intimacy. But if a partner’s commitment is so fragile as to be broken if you don’t speak up and direct all their decision-making, I’m of the opinion that the relationship needs some serious intervention to become healthier.

      9. I agree. This was my first relationship, so I didn’t realize a lot of our behaviors weren’t healthy. I think any extreme reaction – either hiding your feelings to be the “cool girl” or demanding the friendship end – isn’t healthy and symptomatic of other serious problems.

      10. @something random – yes, yes, yes. I agree that it is controlling to demand a friendship be terminated, for no good reason. I was friends with my best guy friend for 11 years. His then-girlfriend (now wife) decided that she didn’t like me, for some reason. I’m still not sure exactly why. We never dated or hooked up, so perhaps she just was jealous that he had a close female friend. We would talk on Gchat often, but saw each other maybe once a year and never texted or talked on the phone. I had met my friend’s gf twice, and I thought it went well both times – I guess not. Anyway, he stopped talking to me with no explanation to me. She also randomly sent me a Facebook message at one point saying she dislikes me a lot, and that my friend would hate her for saying that but it’s true. I’m still very hurt by it a year later, when our mutual college friends got invited to his wedding and I did not, despite me being a much closer friend to him than any of them.

      11. Avatar photo kmentothat says:

        See that pisses me off. It WAS a long standing relationship that was always fully platonic, you had met her and made every goodwill effort, etc. That to me is completely unwarranted cutting off, an he would have been in the right to defend your friendship and work with her on ways to be comfortable with you. Sucks that she was unable to move past her jealousy.

      12. Yeah, it definitely does suck. Coincidentally enough, on the last day he ever spoke to me, I went on a first date with a guy that I have now been dating for a year, and am incredibly happy with. I’m sad to not be a part of his life anymore and sad that he doesn’t know my boyfriend (after meeting past boyfriends where it didn’t work out), but he made the choice. I wonder if she somehow saw me as a threat because I was single. Who knows.

    3. I totally agree. As i said in my post below, some men take advantage of many women’s idea of being the ‘cool girlfriend” who is totally fine with everything always and nothing ever, ever bothers her. This is just unrealistic even in the strongest, and healthiest relationships.

  6. Stillrunning says:

    LW, her wanting to talk about what went wrong is ok as a one time discussion. Maybe she really wants to understand, but if she keeps having those talks with your boyfriend, then she’s not accepting/ respecting his relationship with you. It’s up to him to tell her it’s inappropriate, that he’s with you and that’s the end of the discussion.

    My husband was friends with a woman before we got together. When I met her, it was clear to me that she was attracted to him. After we married, she would call and ask for him without saying hi to me, she kept asking him to come over and fix things in her house, and she told me when she would be over for dinner, saying his late wife had extended an open invitation for her to come over whenever she liked.

    My husband wouldn’t set boundaries with her, so I did. I accompanied him when he went over to her house, and when she called to say when’s dinner, I said we’d be glad to have her over in a few weeks time. As soon as I stood up to her, she found another man and was out of our lives for a while. My husband later admitted that he was relieved she was gone, that he didn’t know how to say no to her.

  7. I don’t get what’s so terrible about admitting that you feel jealous. It’s a normal human emotion. I think going to great lengths to frame it as something else is pretty dishonest and completely see-through. I also don’t think it’s wrong to ask your partner to dial back a relationship with an ex. No, you can’t force him or her to do so, but his or her response will say a lot about why the friendship has continued and how much your feelings are being considered and will be considered in the future. I strongly disagree that it’s fine for someone to fuel an ex’s interest by entertaining conversations about why their relationship went wrong and what a great match they are and I think the LW is right to feel disrespected and I’m sure, despite her wording, that she’s wondering if her boyfriend isn’t enjoying this attention at her expense at best or still interested in his friend at worst. Either way, friends don’t wistfully discuss the failure of their romance or sexmance or whatever, so one or both of them are being shady and this LW needs to get to the bottom of it, respectfully request that her boyfriend stop gassing his head up with constant contact from this other girl or MOA.

  8. While I agree that it’s usually a bad idea to ask your bf to stop being friends with another woman (it just comes across as controlling) I also kind of think that if the bf really cares about LW he’ll dial down the friendship a bit for the moment. If I were newly dating someone I really liked I would make sure to avoid any of the risks involved in keeping a close friendship with a former hookup going. I don’t really buy that he “doesn’t get” that this other girl still likes him, after all they hooked up fairly recently. It would seem obvious that it’s a bit of a delicate situation.

  9. I was in this exact situation many years ago only it wasn’t just one girl at work, it was several. And everyone else knew it. I ended up marrying him after a short courtship and transferring to a different location because I couldn’t stand the flirting and seeing him interact with these women.
    .
    In the long run (20+ years) we didn’t work out and this disregard for my feelings was a sign I should not have dismissed. He was all about him and needed the attention — he was quite insecure.
    .
    LW: I’d keep a close eye on your guy and if this is a symptom of something more major, MOA. It may be nothing but do keep your eyes open.

  10. Ugh honestly, I feel that men nowadays realise that reasonable women want to avoid coming across as insecure and controlling so badly, that they actually use this to their advantage..
    I totally understand you being angry at that girl – she’s going after what she wants and doesn’t care about anyone or anything else, especially your feelings. However, it is your boyfriend who should care about your feelings, not her. I don’t buy that he doesn’t believe she likes him still, I think this makes it very convenient for him to not set any boundaries with her.
    You need to set your foot down but do it exactly as Wendy has said. It’s not good to tell your boyfriend “I don’t want you to be friends with this woman”, but you have all the right to be upset and you should tell him this. And just as Wendy said, ask him what he plans to do to alleviate your worries and make you feel more comfortable with the relationship he has with this co-worker. If he ignores your feelings, this isn’t a good sign You do have the right to feel insecure sometimes and I think this is one of them, he should respect this and make you feel better. You are respectful of his feelings and his friendship with her (very mature of you, good!), but why can’t he do the same with you?

    On the flip side, good thing is that he did clearly choose you over her and he seems to be truthful to you about things, which itself should make you secure in your relationship, alleviate your insecurities and worries. He has obviously prefers to be with you, but he still seems to love the attention he gets from her. And if this upsets you he should do something about it if he respects you enough.

  11. Avatar photo bittergaymark says:

    Insecurity. Insecurity. Insecurity.
    As far as the eye can see.
    Paranoia — being crazy will set you free.

    1. Lol it’s like a haiku!

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