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I (female, 29) have worked with this boss (male, 45) for 1.5 years. He was very supportive, all the time. Recently he got transferred to a different section of my department. I needed some advice on a project that I am working on with a team, so I set up a meeting with him. After the meeting when we were having tea at the office canteen, he just blurted out that he misses me daily. I felt awkward but just brushed it aside.

I have no idea what this means or how to respond. If it's about work, then this is real appreciation. He is really good at his job, and an appreciation from a boss who is himself a perfectionist means a lot. But if it's something else, it would be difficult for me.

Recently, we exchanged Diwali wishes on a chat. He sent me an image of sweets. I thanked him and texted "love sweets". His response "Yeh sweet love". I clarified "nope I love sweets". Then he appologised.

Is he hitting on me? How do I stay away but I need his advice frequently?

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    I would suggest that you maintain the proper professional demeanor and distances, but try to assume the best - he appreciates you as a competent coworker on whom he can rely. – Wad Cheber Sep 11 '15 at 5:34
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    If he's never been creepy to you before, maybe he's just missing the whole group? He's been transplanted to another place and he misses all his colleagues and the friendly everyday chatter, the poor guy's lonely. – RedSonja Sep 11 '15 at 8:12
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    A slightly misleading title, I thought he said this repeatedly to you every day! – DavidB Sep 11 '15 at 10:43
  • Depending on the exact phrasing of the comment, I can imagine lots of ways that a benign comment might be misinterpreted. For example "I miss working with you every day" could be interpreted as "Every day I miss working with you" (creepy) or "I miss working every day with you" (mostly or entirely non-creepy) – bcrist Sep 13 '15 at 20:27
  • shilpa, there is a suggested edit which adds an update to the situation. If this is you, you should log in under the account that created the question and make edits that way. – David K Nov 16 '15 at 19:41
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Whats the best way to deal with the situation

Only you and your former boss can know what his blurted out comment really meant. That said, you were right to brush it aside.

You will be best served by keeping work about work, and nothing else.

So assume positive intent here. Assume that the comment was just an awkward way to deliver a work-based compliment.

Hopefully that never happens again. If it does, you'll need to deal with it at that time.

New development

Recently, we exchanged Diwali wishes on a chat. He sent me an image of sweets. I thanked him and texted "love sweets". His response "Yeh sweet love". I clarified "nope I love sweets". Then he appologised.

If you were part of my family, or a close friend of mine, I'd tell you to stop replying to such texts and that you are encouraging him. If I knew you better, I could tell if you were doing it on purpose and really want his attention, or just don't know any better.

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    I like your answer. Assume positive intent. It is a powerful thing, for any situation! – Puzzled Sep 11 '15 at 6:53
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    Why "look for signs that it was something more"? I would just "assume positive intent" and don't think about it anymore. – Chris Sep 11 '15 at 10:18
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    I like it..... 'to assume positive intent'..... since that day we have had telephonic conversations once or twice a day... purely business talk... he never made any such remark..... – shilpa Sep 11 '15 at 13:47
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    Sorry but -1 for "look for signs that it was something more" - if you look for signs like that, you'll see them, even if they're not really there. I'd say assume it was an accidentally awkward comment and re-evaluate only if anything objectively worrying happens later - don't go looking for things to worry about (apologies if this is what you meant) – user56reinstatemonica8 Sep 11 '15 at 14:44
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    Great, +1 after the edit! – user56reinstatemonica8 Sep 11 '15 at 19:12
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Yes "misses me daily" is a bit awkward but it could have just been an awkward use of words. So far it is a one time thing and the correct response is no response.

You worked for him for 1.5 years and I assume you had no problems during that period.

Don't avoid him but maybe in the future have structured to semi structured business meetings. Make it clear the meeting is not an excuse to talk to him. Politely avoid going to the canteen for tea after. The guy may have a crush on you. Avoid situations that could become awkward. If you do encounter more awkward conversations or actions in the future then be prepared to respond "That could be taken a few ways and I trust you mean on purely business level."

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    I feel you have framed it right "awkward use of words"... it happens with him sometimes..... he does't seem to select his words carefully..... – shilpa Sep 11 '15 at 13:43
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Take it as a compliment on your work ethic and professionalism, don't read too much into a single instance. Bosses moving to new sections are under all sorts of stress and a known friendly face might have just been an anchor in a tough time and therefore you got treated with more familiarity than previously because situations have changed. I wouldn't worry about it unless it happens more often with different undertones.

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His statement could really mean so many different things, and without knowing either of you better, it's hard to say. It could definitely be what you're hoping it's not, but it could also be a lot of other things. Maybe you're a super happy and cheerful person and he misses having someone like you around to cheer him up every day. Maybe you tell him jokes/stories and he misses taking breaks from his work and listening to them. Maybe he's having a bad time in his personal life and considered you a great friend of his whom he could talk to when he was having a rough time.

That said, let's consider the possibility you're dreading. In my ideal world -- maybe not yours, but in mine -- people trust each other enough (and are trustworthy enough) that they would feel comfortable sharing their thoughts and feelings with each other frankly, but they would avoid acting on them in an inappropriate manner. So in my ideal world, it should be fine (if not flattering) to tell someone you like them, with the understanding that you may not take any actions on this inappropriately.
But of course, people are human and we don't live in my ideal world, so it's up to you to figure out whether the right thing is to try to get closer to an ideal world, or to accept the current world as-is.

If you have trust in him, I'd say just appreciate the positive side (i.e. that he's being honest about it) and move on, unless you suspect he's actually going to do something about it that you don't appreciate. He obviously hasn't said anything mean, and it seems that he hasn't given any indications that he's going to take wrong actions, so if the only thing you've seen from him otherwise are positive things, then there's no need to take any actions yet. Ideally, even if he likes you, you can just keep living your current lives and disregarding it. But if you think he might do something that goes in the wrong direction then that's indeed a problem...

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If your boss's statement made you feel awkward then I think your instincts are right. The boss did not say that he could use your experience and skills in his section of the department and why a person with those skills is needed there. He did not say there was a position open in his section that matches your skills and did not ask you if you would be interested in taking up that position. If his statement was about work then he would have also mentioned at least one of these things.

I suggest that you do not meet him in the canteen or any place other than at work, like a conference room or office in your workplace (as another user mentioned in his/her answer). That way you will avoid giving impetus to his wishful thinking. Considering your boss's age, you may also want to to Google the term "midlife crisis" to get a better understanding.

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  • A bit of an overreaction, given that it was one sentence spoken one time, in an otherwise positive and unambiguously work-focused relationship. There's always the possibility that his intentions are otherwise, but someone stumbling over their words and making an awkward statement does not mean they are all of a sudden unable to be trusted. – Jason Sep 11 '15 at 16:41
  • @Jason: Whether it is an overreaction or not depends on the cultural context. In Western culture this would be an overreaction. However the OP's cultural context (easily inferred from her use of terms like canteen, meaning cafeteria - a very common usage of that word with that meaning in India but is rare elsewhere) is different. It is not an overreaction in that culture, something I am very familiar with. By meeting her boss only in office settings and never outside, neither the OP, nor her boss nor their company lose anything. Better safe than sorry. – ZenInTheWorkplace Sep 12 '15 at 0:53
  • Fair enough, my opinion only holds for the US, though "canteen" is maybe not as rare as you think in the Western world. However, my reaction is less about the practical advice (it's fine to only meet in an office setting if there is any question) and more about the idea that there is some certainty that his intentions were inappropriate. Better to act with caution, but believe it was innocent without further evidence. – Jason Sep 14 '15 at 13:49
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There is no need to respond to this at all. Definitely not at this point.

In every company there will be people that you like, there will be people that you don't like, there are people that you don't care about, and so on. All a matter of personality. Most of the time, nobody actually acts on any of these things. We don't go around beating up people that we don't like, we don't go around kissing men or women that we like. But many people go to work every day, and some people they meet every day make them feel better, and some make them feel worse.

It seems that you are someone whose presence is appreciated. Good for you. If you are afraid of any unprofessional behaviour, it isn't going to happen. It hasn't happened when you were working close together, so it's not going to happen now. Right now there is a person who appreciates you personally, who isn't going to do anything stupid, and who has told you so. What you need to do in this situation is nothing. There is no difficulty for you, and nothing to fear.

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It might be awkward but think this: does that in anyway affects your performance at work, specially now that the person that makes you feel awkward is on a different department? If it indeed affects you negatively, which I think is not the case, you may reply to his mails that his messages are starting to make you unproductive. Or meet him "accidentally" at the cafeteria, and tell your piece of mind, since he's supportive, I believe he will be willing to listen.

But if it doesn't make you less productive, now the right question to ask is whether it makes him any, even slightly, productive. If it is, then it doesn't hurt to let him send you the message. While we don't know, maybe he's under some mid life depression (hes forties after all) or maybe the new department is not that welcoming, and by sending some greetings relieves his stress. But if it doesn't make you both less productive, but doesn't make you more productive either, then let him send the message and do not reply anymore, it will stop at its own time.

I just wondering why his choice of are so bold, or should I say: so smooth, "I miss you already". Honestly, as I guy myself, we often do this to people (man or woman) we're really close enough with, or more commonly to lady's we are interested with. Just try to avoid him, and as a guy himself, he will get the message (but that doesn't mean he will give up!).

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If you want to continue getting advice from him, you could try responding by framing it in the context of work, like: "Yes, I miss our team, too. I value your advice and I hope that I can continue to get advice from you in the future", and leave it at that. It just might be that you two have good communication and he felt comfortable expressing himself in an informal way.

Since he is responsible for your performance reviews, it would be unacceptable for him to express personal feelings given his current position of power. I'm sure he's aware of this.

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