I’ve been dating a coworker for a couple months now. He happens to be significantly older than me , and holds a higher work position. Things were going pretty smoothly from the start. I felt secure, taken care of. I was mildly attracted to him, he was very attracted to me. I thought my feelings would develop over time to match his. I was wrong.

The more we hung out, the more I could see his deep insecurities and control mechanisms. I started to feel suffocated, by the praise, the gifts, affection, etc. I found it hard to find alone space and was repulsed by how obsessed with me he was. I know it sounds arrogant of me to say, but it seemed he spent every waking hour thinking about me, planning things, making gifts… it just creeped me out. It made him look desperate and insecure.

Anyway, when we were still on good terms, I agreed to go on a trip with him for about a week. We booked tickets and everything. Now that the days to the trip are approaching, I feel really anxious about it to the point that I’m losing sleep. I know he will expect affection, but I can’t put up with sex, kissing and touching — and he’s very very into it. He also has a way of grooming or, as he says, “taking care” of me. But his grooming is starting to feel more like infantilization of me, like he’s trying to control me. He guilts me if I don’t follow his way, and does so in really sporadic, emotionally explosive ways. Then he reminds me that I am “free to do whatever I want” — but that contradicts his actions.

I’m not saying he’s a bad person. I just feel our chemistry is very badly decaying. I feel uncomfortable and anxious around him, seeking escape, but afraid to hurt him.

The longest my boyfriend and I hung out for was two days. I already told him mostly everything I’ve written above. He says I’m overthinking everything, including the trip.

Should I try my best to keep the relationship together until the trip is over? Or should I ask that we stay friends during our trip, to spare myself of the intimacy he expects?

Tldr; Planned a trip with someone who I do not want to date anymore. I feel anxious and controlled. How/ when should I tell him how I feel?

44 comments
  1. I just read your post history.

    This guy is *YOUR BOSS*?!?

    Good grief.

    Do not go on this trip. Don’t wait to tell him.

    And consider this experience the next time you think it’s a good idea to date someone at work… especially *your boss*.

    Both of you are breaking all kinds of HR rules, no doubt.

  2. >he reminds me that I am “free to do whatever I want”

    Never mind the intimacy, I’d be cancelling the trip.

  3. Life’s too short to subject yourself to this kind of crap. Just drop him and find better, happier pursuits.

  4. Break it off and don’t go! I feel that this is what happened when you hear the stories of “we just went snorkeling and she never came back” and then he just comes back and resumes his life all while she is shark food!

  5. I know you want to see your friend but this isn’t the way to do it. You really really should break up now, cancel the trip and go to see your friend another time, on your own.

    If you absolutely can’t, then I’d still say break up now. But your idea of going as friends is very very unlikely. Either he’ll back out or he’ll go and make you miserable the entire time. But probably less miserable than the kind of miserable you’d be if you had to sleep with him too.

  6. Of course you’re getting the ick for an older man that has to date younger girls. That’s why it’s always creepy and strange.

  7. Atreaction is important. Would you want to date a man who is as attracted to you as you are to your bf?

  8. Unfortunately you let yourself be blinded by the perks. You would have never dated this man if he didnt have those resources. Since you are young and because older men including much older men will try to date you, you need to learn to filter. “Would I date this person if he couldn’t afford these gifts/trips/etc”. If the answer is no, then dont. Over time, it wont be enough and youll grow to resent the person. Then you get grossed by them (the dreaded “ick”)

    Break up with him now. Dont waste your time.

  9. I read above that you’re still going on this vacation. It will be a disaster and will only make him more desperate to hold onto you. He will pull out all the stops thinking that will impress you. I wouldn’t go no matter what kind of promises you have made with a friend unless you pay your own way and get your own hotel room and such. These kinds of men are desperate and only get more desperate when they know they are losing you.

  10. Also learn from this. Make sure you know someone really really well before agreeing on a weeklong vacation. I can barely tolerate my husband and super close friends for a week. I can’t imagine going with a man that creeps me out.

  11. Hell nah first red flag is a 30yr old being interested in a 22 year old that works for him. Beyond inappropriate.

  12. If you go on the trip is will just be a disaster. Better to break up with him now, and let him go by himself and just lose some money than go and have a traumatizing week and be worse off at work when you get back.

  13. You should break up before the trip, and cancel it. Please don’t feel bad or guilty about doing so. Don’t go on this trip!!!

  14. Ima admit i didnt read it all but the part i read where he gives you so much love , gifts etc and it made you repulse saddens me a lil 🙁 cus i kinda like that … me i become obsessed with my gfs and i make them my world. I breath for them and their happyness beocme my happyness and yea hust thought it was sad (i should prolly read the whole thing)

  15. As many have said, don’t go on this trip. It is an option not to go, you just want to and want people on here to validate it.
    No one’s saying don’t go see your friend, that can happen, but personally I’d advise you find money from elsewhere to pay for it and write off anything you’ve previously spent with your bf.
    The fair thing is to break it off now, no head games, no “we’ll go away but you can’t have sex” (now who’s controlling who?). The mere fact you were still going would make him think he’s still in with a shot. And if he’s controlling he’ll make it difficult for you to say no.
    Sorry if I sound harsh but please, just walk away and never look back

  16. OP, if you can’t cancel the trip, can you break up with him and kindly ask him not to come?

    Why would you even consider going on a week-long trip with someone you JUST broke up with, especially an older man that shows signs of being emotionally abusive and predatory? Is it *really* worth your time & money if you’re going to be dealing with his eMoTIoNs and fending off his advances the *entire* time? Do you even feel comfortable sleeping in the same room/bed as this man??

    Please don’t ruin what could otherwise be a great trip by going with him!! it is not appropriate for him to insist on going with you at this point.

    He can be angry, but that’s not your problem.
    and FYI i’d bet money that you’re not going to be on “good terms” with him regardless if he doesn’t get what he wants (i.e. a relationship with you). So if that’s why you’re still set on including him, it’s pointless.

    Please rethink this approach. At least get separate hotel rooms/accommodations. Regardless of what you do, though, I’m proud of you for recognizing the early signs of abusive/toxic behavior and getting away from him. 🖤

    **Edit**: Also, telling him right away is the right thing to do. Just rip the bandaid off. You can apologize for the timing and the fact that he might not be able to get a refund, but hold firm on your boundaries. “This relationship is over and i do not feel comfortable going on this trip with you since we are broken up. I will not change my mind and ask that you respect my decision.” You do not owe him anything more than that, despite what he might think.

  17. Life is too short to do things you don’t want to do. End it now. Don’t go on the trip. You don’t owe anyone anything.

  18. Don’t go on the trip, don’t get trapped with him like that. Read up on cluster B personality disorders, cause his behavior sounds like one. (For the record I am not villanizing these disorders, I suffer from one but am in treatment. Not all of us are toxic. He is, though.)

  19. First off he’s your boss. Second maybe he’s doing all this extra stuff that makes you think he’s insecure because he can probably sense you’re not that into him and he’s trying to please you.

  20. Oh honey. If I were you, I would cancel the trip and break it off with him without any questions asked.

    Otherwise it will definitely get worse from there. This is one of the reasons why you should never, ever date a coworker.

    He was love bombing you, and showing a lot more affection than he should have been. what you have described as far as red flags are concerned or signs of an abusive relationship down the road. **He is definitely unhealthy for you and you need to realize that being without a boyfriend is better than having a POS one.**

    And if he ever retaliates, report the shit to HR

  21. The only thing you HAVE to do in this life is die. Everything else is a choice, just like this trip. Cancel, your friend will understand even if she knows the situation and is ready to step in if necessary. This isn’t worth voluntarily putting yourself in an uncomfortable state physically or emotionally.

    food for thought: If your friend was in this situation and told you “I feel anxious and controlled” (like your statement above) would you suggest they post pone breaking up with their SO and choose to put themselves in an uncomfortable state to push through a vacation? If it’s a no, then why would you put yourself through that?

  22. I had an older guy plan a trip to see me and pay for the hotel and all that stuff a few years ago and he totally blew up when I told him I didn’t want to have sex. I barely got out of the room without being forced or cohersed into it. Then emotionally hurting you for sex is still not technically consent. The red flag are there and frankly the fact that he’s got a higher position in the company isn’t good for you either. Even if you pull out on good terms you may lose your job quite soon after. (with in 6 months) it happens way more than people like to say but if he’s friends with the bosses they can be swayed. Definitely would not go and would put in a note to HR asap

  23. > I’m not saying he’s a bad person.

    I am. He’s showing signs of being a controlling boyfriend. It’s not “arrogant” to not want to be in a relationship with someone like that.

  24. If you feel as if it is not the dynamic or relationship you want anymore then you should end the relationship. You shouldn’t be worried about hurting his feelings. That’s his own end to get over. What’s important is that afterwards you stand your ground and don’t let him make you feel intimidated by your choice or to let him harass you into giving him what he wants that you are not comfortable giving.

  25. RUN, RUN, RUN. End the relationship now. Do not go on the trip. If possible, change reservations so you can still visit your friend without him (I read one of your comments). But if not possible, it’s better to lose money and that visit than be stuck with a guy who’s controlling and creepy, who repulses you.

  26. Rule 1 of the workplace…don’t date a coworker.
    As for everything else, a little bit may be overreacting because some women like that type of affection tion but he is also unconsciously controlling and manipulative with how he does things. Now I’m not saying he’s a bad guy, but it takes a certain person to match his expectations. With that said, don’t go on the trip. You’re only hurting yourself

  27. Get out! Everything you’re saying is red flags. You know they’re red flags, but you’re also trying to be ‘nice’. Honestly don’t be- leave and break it off. These kind of guys prey on younger females bc of the power dynamic.

    Just curious- how much older is this man?

  28. I have to take everything you say about him with a grain because you weren’t that into him from the jump and for whatever reason, you decided to date him anyway. I think because of that, it might be influencing your perception of his actions as an older man trying to take advantage of you or whatever and I don’t think that’s the case (I also don’t think 8 years is a “significant” age difference).

    I think you just need to realize you made a dumb decision, learn from it, and break up. You’ll be miserable on this trip if you don’t.

  29. Being in a relationship where you are repelled by them will hurt them and you will start to start resenting them too. Watching them be obsessed and controlling while you don’t even want to touch them. Watching them want affection and sex ugh no.

    It’s a horrible feeling and you will feel like a confused horrible person staying with them. Once you are not together you will feel free and rid from forcing an interest and the guilt. Also free from their insecure controlling attempts.

    Don’t do it. It’s also taking advantage of him a bit since you know you feel like that while he “likes you” and will get more hurt snd attached as time goes by.

  30. see if you can trade your ticket for airmiles/a voucher so that you can see your friend another time; you could also break up w him & pray he doesnt go on the trip, and then you go anyways

    either way, he’s old enough to be responsible for his off-putting behaviour, and its not your burden to soften the blow of his own consequences.

    as a fellow 22yo, fr do what will make you comfortable most in the physical world; emotional distress over causing a heartbreak is less damaging than physically keeping yourself/your life physically in one spot

    its okay to be kinda shitty when it comes down to your own liberty. get out while you can, it only gets more complicated as time goes on

    finesse, whatever, have fun. if you can swap the ticket for some sort of rewards, do so.

    TRAVELLING IS THE HARDEST THING TO DO W SOMEONE; no need to go through hell for a wk & then hell again trying to justify a break up that he isnt on board with

  31. Download the free app “headspace” and listen to the free read of the day! It might help you on how to say “no” in any situation!!!

  32. honestly, it’s gonna be way safer for you to just cancel the trip before you go than to break it to him during or even after the fact. do what you will regarding the trip, but if your friend throws a fit after you explained why you cancelled, they’re probably not worth it anyway.

    more importantly, the way you’re talking about your boyfriend makes it sound a LOT like this could descend into an abusive relationship later, and if he’s really willing to dismiss your concerns after you’ve brought them up with him, that in itself is a pretty big red flag. i think you should get out of this while you’re ahead, because i don’t like what all of this could potentially spell out.

  33. You are way better off losing the money on the trip. Truly. There is no “be friends” while you’re there.

  34. if youre anxious and losing sleep over this then your body is screaming at you to stay put. listen to the warning signals. you dont have to go.

    break up and stay home.

  35. It’s always amusing when redditors start freaking out on posts like these “Get away asap, he’s going to kill you and wear your skin!!”

    I don’t hear danger from anything you’ve written, except for you to yourself. You’re repulsed, anxious, losing sleep, and still calling this man your boyfriend, and wondering if you should just take this trip with him. You’re going to cause yourself long-term psychological damage if you continue with this man, and this is going to leak into your other relationships. Definitely do not stay together for the trip, break up with him immediately! If you do have to go, like you’ve said, then get separate rooms from each other at the very least! Personally I don’t think you should go at all, cut your losses and go see your friend another time, where you’ll be able to enjoy yourself without the looming presence of a man who disgusts you.

  36. Spending a week in a hotel with a guy I find repulsive and who is going to want to have lots of sex with me sounds absolutely horrible. You do you, but if I were in your shoes, I’d end the relationship before the trip and I wouldn’t go. I’d figure out a different way to see my friends. Vacations can be fun but if you go with the wrong person, they’re can be a complete nightmare too.

  37. Sounds like hes really creepy and that he doesnt have a chill side to him. Being a guy who is overly emotional is no doubt very unattractive to women

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