“Can I Get a Second Chance with My Co-Worker?”

I am writing to get your help to resurrect my friendship with a work colleague who works for me. Basically, she and I (a male) got to know each when she had some problem at work and I helped her resolve it. She also had some issues with her neighbor. Hence, she decided to look for a new house. I gave some practical and first-hand advice based on my recent move. We talked in person and over the phone, texting about a variety of topics in a purely platonic sense. Then one day, since it was getting busy at work, I called her after hours. I confirmed with her that it was OK to do so. I had done so several times in the past and she was fine with it. On that particular day her phone went to voice mail, which I found rather odd. Thinking that there was a network problem, I tried her about five times. Then I sent her a text just to check that she was OK (I had sent texts several times before and she did not object). That day she took offense to the multiple calls and the text. That apparently caused her agony as her partner possibly took offense though I can’t confrm.

Since then, she has been rather business-like and abrupt in conversations. This is despite my profusely, humbly, and unreservedly apologizing to her (on a few occasions) and making it clear that I had no intention of hurting her feelings or hounding her. I am amazed that she was fine with our communication until that day. Not sure what happened that caused her to suddenly changed her attitude.

The year drew to a close on such a sour note while a year earlier we were on great terms. Since we work together and because I genuinely care about people’s feelings, I really want to get back to how things were before. I get on so well with all my colleagues because of my high sensitivity and emotional quotient as well as my spiritualistic attitude.

I would value your advice as I cannot think of anything else to do apart from perhaps hoping for divine intervention! I really want a second chance, which I think is quite a fair thing. My colleague had previously and repeatedly told me how considerate and caring I am, so I really do not want this friendship to end this way if it can be helped. — A Caring but Concerned Male

Hey, guess what – it doesn’t matter if you don’t want your friendship with your colleague to end this way or not; it’s over. And you are not entitled to a reason or an explanation or a “second chance.” Your behavior was unhinged. I don’t even call my husband five freaking times after an unanswered text unless I know he’s at the drugstore and we’re out of toilet paper and it’s an emergency that he picks some up while he’s out. There is literally NO EXCUSE to harass someone like you did – and yes, it was harassment. Calling it “concern” is something only a certain kind of man would ever attempt. That was some straight up stalker-level crap and you know it. And, please, with your “I pride myself in looking after my work colleagues – male or female” bullshit; no one buys it. There’s NO WAY you would call a male co-worker five times in a row after an unanswered text and call it simply looking out for him.

You know what else no one buys? That your communication with your colleague was strictly platonic. I mean, yes, maybe on her end there were no feelings, but you definitely had more-than-platonic feelings for her. She either felt something, too, and came to her senses when her partner caught on and she suddenly had to answer to what your relationship was and she realized it was not something she wanted to jeopardize her relationship with her partner for, OR she felt truly only platonic feelings for you until she got freaked out by your creepiness and then decided to distance herself from you, stat. My guess is the latter. Either way, dude, it’s done and you need to leave her alone and never, ever treat another woman like that again.

I promise, any collegial friendships you have with co-workers are NOT – 100% NOT – the result of your high sensitivity and emotional quotient and spiritualistic attitude. Work friendships are rarely formed as a result of any of that. What fosters work friendships is a sense of humor, being helpful (but not overbearing and creepy about it!), loyal, and respecting boundaries and discretion when warranted. Spirituality? Nah. Emotionality? No. Absolutely not. I really think that the things you believe are attracting people to you are what pushes them away. I’d advise doing the opposite of what you’ve been doing if you want to be liked at work: stop trying to fix people’s lives; don’t call and text after hours; don’t try to be spiritual, you aren’t on a retreat together; and for the love of God, don’t stalk anyone. Also, if you’re really “traumatized” by the “sour ending” of a casual work friendship in which you conducted yourself inappropriately, you might want to talk to a therapist. It’s normal to feel regret in this kind of situation and embarrassment and maybe even a little sadness that the feelings you developed weren’t reciprocated – all emotions that a little time would quickly ease. But to feel traumatized suggests the need for a deeper unpacking of this, some guidance on how best to move forward, and maybe even some help reading social cues.

From the forums:

I’ve been dating my boyfriend for about six months and really like him. He is 30 and I’m 25. He’s been married before and I’m struggling to come to terms with the fact that he loved someone else that much and that he has already had a proposal and big fairytale wedding so that it wouldn’t mean as much to do it again with me.

I’ve dated a fair bit before but haven’t been in a relationship longer than six months and have never been in love, but I am starting to feel that way about him. My boyfriend, however, was in a relationship for seven years total, living with her for four. She left him for someone else less than a year after the wedding and after having an affair. He was heartbroken and says he did not see it coming, but now he feels conflicted about her as he loved her so much while on the other hand she hurt him.

This was three years ago, and while he does seem to really care about me, it took him a while before he could talk about it or even tell me he’d been married before. I worry that deep inside he’ll never get over her and I’ll never have his whole heart.

I know this might sound unreasonable and everyone has a past, but I’m struggling to accept this. Do men always hang onto an old love and can they fully recover from heartbreak? I’ve read men take divorce harder than women do. — Rebound Love?

Men are not a monolith. There really isn’t anything that all men do or don’t do except maybe they all think about sex and pizza at least once a day. But, no, men don’t “always hang on to an old love.” They might be sad and depressed and lonely and feel rejected for a little while, sure – just like some women would be. Some might feel these things longer than others. Many will move on the minute sex or really good pizza are offered; they just aren’t that complicated, to be honest. Maybe your boyfriend is hung up on hs ex, but literally nothing in your note, or in your update, indicates this is the case, and I have a feeling that if there were red flags worth mentioning, you’d have mentioned them. Nothing about your boyfriend’s behavior suggests he’s not over his ex.

What *is* suggested in your note is your unhealthy obsession with your boyfriend’s past, and I promise it is getting in the way of your moving forward. If you want your relationship to be your first to move beyond the six-month mark, you have to focus on what’s in front of you: focus on your feelings for your boyfriend and how he expresses his feelings for you; focus on spending time together, getting to know one another (not through stalking social media pages of people in his life), and having fun. Life and love and relationships can be complicated enough; you don’t need to go looking for complications. Let things unroll organically. And if you’re having trouble doing that, figure out some way you can process your anxiety – exercise, hobbies, talking with friends – that takes the pressure off your relationship.

Think of your relationship as an egg you’re balancing on a spoon as you get from Point A to Point B. The more you think about what happened before Point A, the more the egg wobbles. The more you squint past Point B to see if you can make out what lies ahead, the more the egg shakes. Keep your eye on the egg, focus on the right now, keep taking one careful step in front of the other, and you might just surprise yourself with how far you can take this egg, er, relationship…

***************Follow along on Facebook,  and Instagram. If you have a relationship/dating question I can help answer, you can send me your letters at wendy(AT)dearwendy.com.


  1. LisforLeslie says:

    LW1 – You can try to convince yourself that your BS isn’t BS; but it’s total BS. I’ve been working for close to 30 years and here’s how many times I have repeatedly called ANY of my coworker friends: 0. That’s both on and off hours.

    You can try to spin it all you want but you can’t force the toothpaste back in the tube. She’s allowed to set whatever boundaries she wants and you have to abide by them.

  2. LW1: Everything Wendy said, plus, you absolutely do not have a high EQ. You literally have no clue. What you *have* is a potential HR problem here, so snap to it and cut the shit lickety-split or you’re going to be in a world of hurt.

  3. LW1: Calling someone five times in a row because it went to voicemail, and adding a text?? That’s *unhinged.* Maybe she was in the bathtub. Maybe she was ill, which is none of your business, concern or not. Maybe she was having sex. Maybe she turned her phone off, or it died, or she just didn’t feel like chatting with you. Jesus, I don’t call my *parents* that often if they don’t answer, and they almost ALWAYS answer.

    I’m going to echo Wendy’s call for therapy, because you need to learn to read people better, or you’re going to drive away anyone who possesses more subtlety than a sledge hammer to the head.

  4. Bittergaymark says:

    LW1) Are you autistic? As that’s the only thing I can think of that would possibly explain 5 ohine calls in such rapid succession. Sorry, but yeah. I think this friendship is over. And that the frantic calls were driven by a crush of some kind. It’s all… VERY excessive. Be polite and casually friendly. Like super casually. But honestly? I wouldn’t expect much.

    LW2) Your insecurities are your hang ups. You need to deal with them. I’d suggest professional help as there is little real basis for your fears here. You are literally dreaming them all up. They will doom this relationship if they go unresolved…

    1. Karebear1813 says:

      Hmmm I wander if LW1 is autistic too. He seems highly intelligent in narrative but clearly is missing social cue boundaries.

      1. Karebear1813 says:


      2. ele4phant says:

        I dunno, my first thought was not a native English speaker/writer.
        Some of the phrasing felt very formal, technically correct but not how native speakers use the language.

        Who knows, regardless, totes inappropriate for a boss, or anyone, to hound someone as much as he did.

  5. anonykins says:

    The only people that have ever called me that many times in a row are my mother (estranged for 5+ years, my choice) and my partner (currently looking at divorce). So. Yeah.

  6. Anonymous says:

    Once I accidentally texted a coworker senior to me “I’m not happy” at around 7pm. The text was meant as a joke for my husband in reply to him saying he was running 20 min late but I accidentally tapped the window of a recent conversation with my coworker (i was to meet him at a location for a meeting the day before hence why we had a recent chat). My coworker was very concerned and called me multiple times but I missed them all and he sent multiple texts. He said he thought I was going to commit suicide. When I checked my phone at like midnight I saw all these missed calls and was like huh and only realized after I opened our convo what happened. Kind of extreme but I laughed it off. This letter made me think of that.

    I have no advice except maybe just move on and don’t bring it up. Thought it was a funny story to share.

  7. LW #1 — ” my friendship with a work colleague who works for me. ” So, you pulled this crap with a subordinate. That is bad. It is almost certainly contrary to company policy. If she wanted to, she could get you fired as in “I’m afraid that I’ll be disadvantaged in my career by this creep boss who has a crush on me and won’t stop contacting me.” And this “her phone went to voice mail which I found rather odd. Thinking that there was network problem, I tried her about five times.” So, she has a physical record of your multiple calls, which she can turn over to senior management or HR if you don’t back way the hell off. At this point, if she wants, she owns your future at this company. Any impartial observer is going to be convinced that you have a serious crush on her. I got that just from reading your version of events. Just imagine how damning her version will sound, especially to a manager who has observed how focused upon her you are.

    LW #2 — same answers as on forum. I’ll add that you are 25 years old. That’s old to not be able to handle the fact that your SO has a romantic past. It will be incredibly hard to find a guy, especially if you date 30-year olds, who doesn’t have at least one serious relationship in his past. Who does that leave you to date, if you can’t fix this insecurity?

  8. golfer.gal says:

    I agree with Ron that for LW the fact that this colleague isn’t a peer, but a subordinate who reports to you is a giant, huge, big deal. There is a power dynamic at play that means bosses shouldn’t try to be personal friends with subordinates. They should not involve themselves in their personal lives. They should not be calling or texting after hours. Why? Because subordinates feel pressured to consent to unwelcome behavior out of fear their job or future opportunities will be jeopardized if they don’t. If this was a run of the mill coworker the behavior would be over the top and not ok. The fact that it’s a subordinate makes this egregious.

    There is also something really off-putting about the language you use. You apologized to her for “hurting her feelings”. This makes it seem like her perception or reaction to the situation is the issue. It’s not. It also comes off as, frankly, sexist. You didn’t hurt her feelings. As her supervisor you crossed a professional line that has potentially impacted her standing and career at the company and has caused her to justifiablely question your judgement. You talk a lot about your intentions and how great they were. That doesn’t matter. No matter how pure your intentions, your behavior was inappropriate and, by your own description, is a pattern of inappropriate behavior with subordinates.

    As for what to do now, I’d say you need a complete reset on what it means to be a boss and your boundaries. Start reading the Ask A Manager blog and do some research on boundaries at work and what good leadership looks like. No more “friendships”, no more texts to her personal phone, stay away from her personal life even if she brings it up. Again, even if she “consented” to these things you have no way of knowing if she actually wants them because YOU HAVE POWER OVER HER. It is your responsibility not to make those asks or expect your employees to fill the space of personal friends in your life. She has reset to a strictly professional relationship, and you need to do the same. Maybe down the line you can have a conversation where you apologize for your behavior (not her feelings) and explain the steps you’ve taken to become a better boss and what you’re prepared to do to support her professional growth. That is if she doesn’t go to HR first, which she would be well within her right to do. Or if she doesn’t get the hell out of dodge, because if I were her I’d be cashing in every connection I had looking for a new job.

    1. golfer.gal says:

      Also, you describe “getting to know her by helping her resolve some problems at work”. Again, YOU ARE HER SUPERVISOR. That is literally your job. Your language is signaling that something is really, really off. This wasn’t a meet cute or a naturally developing relationship because you did her a solid at work. She works for you. You should not be calling and texting her about a “variety of topics”, and I agree with Wendy that I don’t care what you say, I seriously doubt you’re acting this way with your male reports. There’s a mix of entitlement, sexism, deliberate misperception and objectification in this letter that is really concerning

    2. If she goes to HR, which you better hope she’s too scared to do, LW, you’re going to look really bad trying to explain the situation and your motivations, as you do here. Trust me on this. Do not make any more overtures toward friendship with this subordinate. Don’t push it, and your luck may hold. Push it, and you could be called into a meeting with your boss and HR for an official reprimand.

      1. In case I’m not being crystal clear, HR will ask for your side of the story, and if you explain it like you did here, they’re going to be seriously concerned.

      2. ele4phant says:

        So totes could be wrong, but I get the impression that the LW might own his own business or something? I don’t know, I suppose “works for me” could still be the wording someone might use if they work at a huge company in a mid-level position with direct reports, but I just kinda get the feeling this guy has his own business with a couple employees or something and he hires his friends/people he thinks he could be buddies with/finds hot.

        So, maybe no HR for her to turn to. I mean, she’d definitely have recourse beyond the workplace, but that’s further down the road if he continues to be be a creep.

  9. Thank you for calling LW1 on his bullshit!! Dude, you’re intense. You need to dial it way the fuck down. Your coworkers are not your friends. Be professional

  10. Karebear1813 says:

    Oh WOW LW1 – WHY OH WHY did you call this person 5 times in a row and then proceed to text thinking this is normal behavior. This is creepy/stalker behavior. And to top it off you are her supervisor. This is 1000000% all you and if I were you, I’d leave her alone as much as possible. Hopefully she will find employment elsewhere or maybe you should. YIKES!
    Wendy’s Advise as well as everyone else was great to read.

    1. Yeah, even if they didn’t work together, people are allowed to not answer their phones if they want. LW’s behavior is way out of line under any circumstances.

  11. ele4phant says:

    Not to reference another advice giver, but Askamanger posted a similar post: A generally reliable employee didn’t show up, they knew she lived alone and had diabetes, they (was a husband and a wife pair in that letter) went to her home, she didn’t answer the door or their calls, they called the police and they came in and did a welfare check, got the apartment manager to unlock the door – and whoopsie she was home with a guy and had in fact called them and left a message she wasn’t coming in.

    She was pretty pissed and the working relationship beyond repair. AMA thought they were bonkers – and so were you.

    Not even taking into account the overtones of you having a personal relationship with your employee (are you just friends or are you romantically interested in her and claiming otherwise), as an employer, you don’t hound anyone like that. If an employee doesn’t show (or is unresponsive after hours which was your situation), you give them one call and maybe an email that’s like “Um, everything okay? Was expecting you/was expecting to be able to reach you”, then go about your day. When you do hear from them you can have the manager chat that “You really can’t go AWOL on work, what happened there?”

    Generally speaking, it’s best not to hire friends/people you have crushes on.

    You done screwed up.

  12. LW1: one word: BOUNDARIES!! Get some, learn them, use them!

  13. “… her phone went to voice mail which I found rather odd. Thinking that there was network problem … ”

    Nope. It is the most normal thing in the world, not at all odd, for a call to go to voicemail. I too am wondering if the LW is autistic.

    1. Bittergaymark says:

      This very line in particular gave me that same idea.

    2. Exactly. If there was a network problem the phone likely wouldn’t have done the extremely normal thing of going to voicemail.

  14. LW1: you are not “caring”, you have control issues. You want to control this co-worker. Advice, calls, checking on her for work out of hours… you just need to dominate. And you sign “Male”. Yeah, got it. Stop it. Stop thinking that she works for you. She work under your supervision, or for your company, but not for you, ok? Stop with your grandeur. Just be professional with her. You will do her a favor.
    Remember, as an subordinate, she can’t escape you. Respect her and don’t impose all these personal expectations on her. Just do your job.

  15. And even if he is he owner of a small company, as some have suggested (in which case the use of ‘co-worker- and ‘work colleague’ strike me as odd), her time outside of work is her own time, not he owners. If things are too busy at work to talk to her on Tuesday, then talk to her on Wednesday — AT WORK! The concern truly seems to be not for her well being but out of fear she is with another guy.

  16. Avatar photo Guy Friday says:

    LW1: You know what? I call my coworkers (who are arguably my subordinates) after hours sometimes too. I don’t find that necessarily odd. But do you know what I do when I call and it goes to voicemail? I drop them a quick text saying “Hey, if you get a free moment, can you give me a call about XYZ? Thanks!” Then they know what I’m calling about, and if they want to call me back they can. If they don’t? Ok. If it’s urgent, that text says something like “Sorry to bug you, but I really need to talk to you about XYZ. Can you call me back as soon as you get this?” What I don’t do, as others have pointed out, is call more than once in a row. If I’m going to do that, there had better be a life or death emergency I need to talk to them about. My advice to you, beyond echoing what everyone else has said, is that if you want to ever have a chance of being friendly with this person again then CHILL THE FUCK OUT and let them decide when they’re ready to reengage. The more you push, the more unhealthy your view of them looks.

    LW2: I don’t mean this to sound harsh, but did you ever consider that the reason that your boyfriend didn’t tell you right away is because he sensed you’d find him to be broken even if he wasn’t? If being married and divorced is a character flaw you find in him, break up with him; he can’t change that part of his life. But to doubt him when he’s really shown no signs that he loves you any less than fully is unreasonable. Or, more importantly, TALK TO HIM and let him know your concerns. I can’t imagine any decent person wouldn’t recognize that you’re struggling a little with this and reassure you of his commitment.

  17. LW#1…wow. First of all, if my long-term boyfriend called me 5 times after getting my voice mail, I’d be PISSED. Leave a voice mail…I’ll call you back when I’m free! If it was my boss, calling after-hours for personal reasons and not a work emergency (and ONLY an emergency), I’d be terrified, pissed, and looking for another job. That’s way out of line. If this woman works for you then you have power over her and a responsibility to not abuse that power. Your intentions don’t change the effect of your actions on her. Set some boundaries (no outside-of-work interaction with subordinates is a good one!) and give her space.

  18. allathian says:

    Yikes. LW1, calling your subordinate a coworker is disingenuous at best. You’re her boss, so you have some power over her employment.

    If you truly care about her and want what’s best for her, accept her boundaries. She seems to want to stick to being strictly professional with you, so take her lead on this. In future, don’t try to be anything but a good manager to your subordinates, male or female. With the power differential between you, there can be no truly genuine friendship, so stop fooling yourself.

    I’m hoping she’ll see sense and can manage to get a different job with a more reasonable manager.

    Also, if you can’t offer her a genuine apology, don’t apologize. Especially, don’t think an apology lets you off the hook and never, ever make the mistake of believing that an apology will let you go on behaving as if nothing had happened. She’s going to think you’re a creepy jerk for a long time. Let this be a lesson to you in how you shouldn’t behave with your female subordinates.

  19. On LW1, I’m so appreciative of everything that has been said, that I won’t add anything. Good work DW!

    LW2: You are still fairly young and have the idea that marriage and love is forever, which is a wonderful thing, but in my opinion it’s closer to fact that people, whether alone or together, grow and change over time. Your boyfriend had a big fairytale love and wedding with a woman who was right for him at that time, and is not right for him now at this time. He is 30, this marriage is not going to define the next hopefully 70 years of his life.

    Consider this in a really, REALLY over simplified way – remember those jeans you absolutely loved 10 years ago and thought nothing would ever suit you better and swore to wear them every day until the day you died? Looking back, does the style make you cringe?! Everything changes. 🙂

  20. LW1 definitely has cringy r:niceguy overtones. Ew. And something a lot of these guys have in common is that they believe they are special, that they’re better/smarter/more sensitive than other guys. Someone may have told them that once and they’ve clung to it. They also think they have much closer connections with people than they actually have.

    He needs to get some help so he realizes she doesn’t owe him anything and he can leave her alone. He’ll never realize he’s a creep on his own, he’ll just think we all don’t understand.

  21. Anonymous says:

    #“Can I Get a Second Chance with My Co-Worker?”,
    Some of my co-workers became friends with each other and they stay connected on social media, invited over to family events, share foods at work, eat out at restaurants and of course there are some co-workers strictly co-workers only. I don’t know the whole story or what really happened between you two that caused her to change her attitude over night. I’m sure it did not start with multiple calls or text. But it started with the unanswered first phone called (why?) which she obviously had decided to not answer your phone for whatever reason she’s not telling you or mad at you. People don’t suddenly changed their attitude over night for no reason(s). If you believe she misunderstood you for something and she has different views as you and refuse to listen to you. I would recommend that give your co-worker-friend space as long as she needs and let her live her life. Meanwhile you trace back your steps of what you did or said to her before the night she decided to unfriend you. After she’s all cool then ask her for 5 minutes of her times to hear you out because you value the friendship with her.

    You may value the friendship with her but she may not have the same level of value as you. Otherwise she would have come straight forward and tell you her friend what’s really bugging her or ask you to stop whatever is bugging her. She didn’t need to take the extreme road of unfriended you as the last result. And left you hanging wondering why.

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