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female
age
41-50,
anonymous
writes: Hi guys!I haven’t dated in a long time, so I have no ideas what the “rules” are. Also, I haven’t been able to shake off the weight I gained during my divorce (it started during my marriage), which makes me insecure. And so does my age (45).My husband and I parted our ways after almost 15 years of marriage over a year ago because we were too incompatible. He now knows that he will never change, seek therapy for his mood swings, outburst of anger, anxiety… and I’ve learned that I cannot help him and that I cannot not live my life walking on eggshells and neglecting my needs (my weight gain wasn’t only stress-provoked, I was taking care of him more than I was tending to my well-being). We’re family. I can understand when some exes say that they are like brother and sister. I think we were like that for a very VERY long time. I met a guy at work, and I felt attraction about 9 months ago. He’s single, in his early fifties. As I got to know him, I realized that I like him too. That it wasn’t “just” chemistry. And I think that he might like me too. Here’s the thing, I don’t think that office romance is a good idea. So, I would never ever even be thinking about this, if it weren’t for the fact that I’m leaving the firm for another job. And the guy is also my director. There’s that. Soon to be ex-director. We have always had a good working relationship and I have done everything by the book resignation wise. They have had enough time to find someone I could train. So, everything is fine in that department as well.My question is, should I wait for him to ask me out, if he’s interested at all or should I “bite the bullet”, not knowing if he likes me, ask him if he’d like to have coffee with me? If I decide to wait, I don’t know how long should I wait before I know that he’s not interested a day, a week, a month? I am going to live my life anyway, regardless of his actions, I was just curious about how things work these days. I’m NOT on social media, by the way. So, if he wants to know things about me or ask me something he has to contact me (call or text). He knows far more about me than I know about him, because of his position. I have no idea if he’s divorced or if he has kids. I know that he’s single because he mentioned it in a very casual way.Thinking about asking him out is surreal because I am attracted to him. If it weren’t the case, If I liked him as a friend only I’d like to keep after I leave, I would have asked without thinking about it and I would not worry about what he would say.Here’s why I think that he might like me. First of all let me say that he has never ever done anything inappropriate. He always acts like a gentleman and in accordance with the positions we have at the firm. Needless to say I do to. I have never flirted with him. Having said that, whenever I’m in the office (I also work from home, so I’m not always there), he seeks my company. That’s just a fact. He comes by my office casually, just to say hi and always initiates conversations. He always stops to do that even when he’s in a hurry. If my door is closed, he knocks, comes in, and then we talk. He always finds a way to keep the conversation going. I do too. But it’s not like we have to make a big effort. He doesn’t do that with anybody else. He also always comes to the common room when I’m there. Btw, nobody else ever is. He never used it until he figured out that I do. So, whenever he doesn’t have to go out to business lunches and I’m there, there he comes. He never uses it when I’m not there. He mentioned it himself. He usually brings his lunch, and we casually talk. When I have work to do, which is very often the case, he’s still there, just eating his salad sitting on the couch or reading. He’s an avid reader, I guess. The silences are never awkward. He’s the first to step up when I need something. I don’t need things often and they are not big things. Our receptionist could help me out with most of them, but he wants to do it (so maybe he likes our receptionist, Mike?! ??). He even goes a few steps ahead, thinking what I could need at work. That’s something he does with work in general, but instead of organizing others to do this for me, he does it personally to make sure that everything is covered. If you ask how he knows I need little things if I don’t ask him. Well, his office is just behind the receptionist area, and his door is always open. He hears me asking and then he just comes out. Mike is always happy to let him do it. That’s for sure.He has my number on the list of priorities, which means when I call the firm it goes straight to him not to the reception. I’m not the only one on that list, sure, but I wouldn’t consider myself a priority. I’m just an employee. I’m not a manager, even if I have a “special mission”, I don’t work with him directly on daily basis. This can be only work-related thing. Btw, I don’t have his mobile number. He has mine (and so does Mike) and he uses it when there’s a change of schedule or something. He never calls me just because. He never gives me any preferential treatment. He doesn’t confide in me, but he trusts me with delicate information that I need to know, even when they are not yet to be publicly shared.He never asks me to stay late at the office or invite me to business meetings (there would be no reason to). But I’ve seen him so many times just watching me when I give a presentation for e.g. to newcomers that he knows by heart and that I do exceptionally well (and he knows that). He doesn’t have to be there, but when he has the time, he comes. At first, I suppose he was evaluating my work, but later, there was no need to. And he’s not the type who doesn’t delegate. He has surrounded himself with excellent co-workers. He always finds a way to complement my work (never me personally, he never comments my appearance) and when he needs to criticize, he does it constructively and offers help if there’s anything unclear. This is difficult to be objective about, but I think he might like me because he always makes eye contact and just keeps it. And he smiles a lot when he looks at me. He tends to stay close to me (not awkward close, but close) and then he remembers the covid rules and moves back, and then he forgets again and moves closer. He remembers things about me; things that I have said or did and then if there’s something he can do about it, he does. For example, air-conditioning and draft make my neck stiff. He always turns his air-conditioning off when I enter his office or the meeting room. I’ve paid attention since the heat wave hit us just to make sure I’m not making this up. He laughs at my jokes. So do other people. I can be witty so I’m not sure if this counts. As I said, I don’t know anything about him. He could be lying about being single, but he doesn’t come off as a player. There are many other women in our firm and as far as I know, he has never flited with any of them. There was one who was obviously interested in him, openly flirting with him, but he never her any encouragement. He wasn’t looking to boost his ego. I know that he competes in the tennis amateur league and volunteers at his club as an assistant coach for children. He’s very passionate about it. I get that. I volunteer at a local coup kitchen and a retirement community. Other than that, I have no idea who he is. But I’d like to find out. Maybe he’s a jerk?I know that you won’t be able to tell if he likes me or if he’s just being nice. Am I crazy in thinking that there might be something there?Should I let him call me?My only worry is that I haven’t really shown him how much I liked him, because he’s my boss. I haven’t shown him I disliked him either.Btw, my freind have started at some point to set me up with some of their friends. And I have met a few really wonderfull men, but I haven't felt this attraction to them and I haven't seen that they reacted to me in a more than a friendly way. Apart from one who was trying really hard because I "fit the bill". There were some guys whom I met who liked me, but I didn't like them enough to really get to know them. The man I mentionned is the only one whom I felt any attraction to. And I know he won't be the last. I just don't want to miss the opportunity.Sorry for the length of this post.Thank you!
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at work, co-worker, divorce, flirt, insecure, my boss, player, text Reply to this Question
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Fancy yourself as an agony aunt? Add your answer to this question! A
male
reader, anonymous, writes (24 June 2022): He won't be offended, so why not ask him?
He clearly likes talking to you so he will probably accept!
Best of luck.
A
reader, anonymous, writes (24 June 2022): Nothing ventured, nothing gained, sister! Well, that's what some would say. Not me!
I don't read much into peoples stares or treating me nicely. I expect to be treated nicely; because I treat others nicely. If you're a single-lady, and you haven't met many eligible men; you may target a guy with all the right attributes...I'll say this at the risk of coming across like a pessimist... I think a man in his 50's is far too old to be playing games. Your post is very lengthy about it, and you might seem a little desperate or anxious.
Most of the stares I get are from people trying to figure-out what race I am? I'm bi-racial, and we're now in a world that's highly sensitive to ethnicity and nationality. Is being nice to people and taking interest in their work-ethic or admiring their professionalism always construed as a romantic interest? I'm now scratching my head, and would have to wonder.
I suppose he's being as cautious as you are, because you are a work colleague; and the minute he makes a move of a flirtatious-mature, he doesn't know if it will fly back in his face as a sexual-harassment charge, or a complaint about inappropriate behavior. Which is a pretty sticky situation for us men these days. People do misread body-language, and take stares for interest; when sometimes people just stare...because that's just what some people do.
He may not be interested in more than in a professional way. For me, work is not a good place, in today's litigious society, to put your livelihood and reputation on the line. If you let the woman know you weren't interested; then she may be insulted, and react in some unexpected way. It's just putting a little too much on the line.
My advice isn't so much to you as it would be to men reading your post. I don't think it's a good idea to "stare" at women on your job. It could get the reaction you're hoping for; or it could be a very very bad-one! The question for a guy is, is it worth the risk? What have you got to lose? Probably, everything, if you make the wrong move. Too much of a gamble these days!
If everybody has to dance around each-other waiting for somebody to make the first move; it's an indication that it's a bad place, wrong timing, or absolutely the wrong situation to be seeking romance.
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reader, anonymous, writes (24 June 2022): Testing
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female
reader, anonymous, writes (23 June 2022): Here's how I see it (and I read your post twice):Fist of all I love the Youcannotbeserious' answer. It's uncomplicated, elegant and allows you to act without feeling stupid if he says no, because the stakes aren't high.It's good that you are aware that you don't know this guy. You have no idea how many of my friends do not know a difference between attraction, liking someone, falling in love and actually loving someone. In your shoes, some of them would really put themselves in an awkward position. You didn’t, good for you.However, being the boss means that you cannot be really sure when people are nice to you because they genuinely like you (as a person or as a love interest) or if they cannot risk acting ambivalent or even openly disinterested, so they just laugh at your jokes and make you feel appreciated. I’m sure that he has figured out by now that you being nice is you being interested in him. Up to a point. But don’t forget that being a boss also means not pressuring your subordinates and making them feel obligated to accept their advances. My point being, unless he does something in the time you have left in the firm (with you leaving for sure would be totally acceptable), you should have a go, or you will never know.You ask about the dating “rules” nowadays. I don’t think that much has changed. Men still like to be the ones taking the lead. What I like with the YCBS idea is that you are not taking this away from him. You’re simply giving him a greenlight. Saying that you’ll miss “your chats” is enough for him to stop doubting but it’s not aggressive in any way so that he might feel threatened, whether he likes you or not. You’ve got nothing to lose. Also, MeToo has (thankfully) changed some things. He’s probably a nice guy to begin with, but today he is more than ever aware of the power play that exists in these circumstances. So, give him some time to do something and if he doesn’t, you do it.Does he like you or not? There are so many things you don’t mention in your post. For example, what the atmosphere in your firm is. Does he get along fine with most of the employees? So, let’s get this scenario out of the way. If he’s not feeling lonely and unsupported (finding his only friend in you), I think he likes you. Of course, there’s always a possibility that he’s bored and needs this kind of stimulation at work, but it doesn’t happen that often and in which case you would not like to spend any amount of time getting to know this person. They are usually narcissists. Don’t let the feelings you have for him block you. You have nothing right now and if he doesn’t do anything, even after you do something, well you’ll have something – you’ll know that he’s not for you. This should NOT affect your self-esteem, because after all you don’t know what he has going on in his life and maybe he’s not ready at this moment for dating even though he likes you. I’ll repeat, if he didn’t like you and he acted in this way to feed on your affection/appreciation, he’s not a good guy. And I’ve known some guys like that. They are usually more open with the display of their affections because they want to get you hooked.Another thing. Don’t be self-conscious about your body. Lose the weight for your health and overall wellbeing. If he’s a real man, and if he hasn’t dated 20 year olds all of his life, he knows what a mature woman’s body looks like and more importantly he knows what to do with one :)
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female
reader, Youcannotbeserious  + ♥, writes (23 June 2022):
 P.S. Forgot to add, as you seem to have your heart set on this guy, until you know there is no chance of a relationship with him, it might be a good idea not to date other guys. No stranger will match up to someone to whom you have felt attracted for 3 years.
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female
reader, Youcannotbeserious + ♥, writes (23 June 2022):
I suspect there are two people here who are both terrified to make a move as neither of you is sure of your ground because both of you have acted in a "professional" manner and neither of you has made it obvious how you feel.
There are 3 possible outcomes to this scenario:
1. Neither of you makes a move and you both wonder "what if?".
2. One of you takes a risk and things don't work out.
3. One of you takes a risk and things DO work out.
In your shoes, I would mention, during one of your chats, that you will miss them when you leave and you would love to stay in touch. If he is interested, that will give him an opening.
Good luck. I do hope he steps up.
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female
reader, Youcannotbeserious + ♥, writes (23 June 2022):
Testing testing - as I am fed up of typing out replies and then the system crashing and not allowing me to post them. If this appears, I will reply properly.
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