A
male
age
36-40,
anonymous
writes:I have a crush on my boss. She's around my age, and as far as I know, she's not currently in a relationship. She has a lot of the same interests as I do, and she seems like a really nice person. She's also not that high up on the management ladder to where it would be a problem if we started dating. But before I even think about dating, I like to develop an atmosphere of familiarity before I ask a girl out. Unfortunately, because our work requires us to be apart for long periods of time, and we're rarely alone together for longer than a couple of minutes, I can't establish a connection. I don't want to scare her away by outright asking her on a date, but I don't know what other option I have. What should I do?
View related questions:
crush, crush on my boss, my boss, period Reply to this Question
Share |
Fancy yourself as an agony aunt? Add your answer to this question! A
male
reader, robot  +, writes (5 March 2010):
I have a critisism to make of you, and it is that you have created a very neat catch 22 situation that means you are justified in avoiding the difficult step of making the first move. You need some familiarity to ask a girl on a date, but A DATE is where you get some familiarity. The lesson you are teaching yourself is that if there is something risky to do with an unknown outcome, you can contrive a simple excuse, and then you can rest, guilt free, in the knowlege that you have once again avoided making a fool of yourself. So congratulations on making your life perfectly safe and free of disappointment.
Or you could ask her out on a date involving one of those shared interests you both have, and if she says no thanks, say, ok and get on with the rest of your day.
A
male
reader, anonymous, writes (5 March 2010): I have some people working for me and I have also been working for people so I have a bit of an idea in both situations.
I have always tried to be extremely cautious at work, with my employees and same with my higher-ups; I have always avoided anything that could remotely look like any kind of interest, sexual or merely unprofessional.
Having said that not every job situation is the same and not every romance situation is the same, so I cannot agree with those who make very strong judgmental suggestions here.
For example, if you work part-time at Burger World, and your boss is the branch manager, and you are hopelessly in love with her, GO FOR IT! Ask her out; the worst thing that can happen is that you will end up looking for a different job but, on the upside, you may improve your life tremendously by being with the woman of your dreams.
Different scenario: You and your boss are working in middle management at a large corporation in Topeka, where people typically work for their lifetime and everybody knows everybody. You have a mortgage on a house there and a well-paid job and don't plan to move town or jobs. Plus, the work environment is latently hostile and known for bitchy and curious coworkers who will do anything to appear important. In this case....well, asking your boss out or doing anything remotely unprofessional would probably not be a good idea.
Bottom line: Only you can tell for yourself, and your particular situation is likely going to be in the middle. Listen to your feelings. Oh, and good luck man!
...............................
A
male
reader, Artfuldodger  +, writes (5 March 2010):
How about organizaing a small work lunch to a nearby restuarant. Invite 5 or 6 people and invite her as well.....that should be a good start. will give you guys some time together...It will give you an idea if she seems interested, if she does.......ask her right there and then that you guys should go for drinks after work sometime, and schedule a date...don't beat around the bush...go for the killAs for the whole, be friends before asking her out....its a myth..doesnt work...its a lie, and has always always backfired for me....don't try to be her friend...
...............................
A
male
reader, anonymous, writes (5 March 2010): I've tried the whole getting to know the girl first before asking her out and every time I adopted that method it backfired on me. I really recommend you simply ask her out. Doesn't have to be anything fancy, but be direct. Don't waste time.
...............................
A
male
reader, $izZle  +, writes (5 March 2010):
 hey, i do believe that you need the classic approach ... write her a letter with your feelings and tell her that you would like to know her better ... maybe she is a modern uptown girl but she will like to know that some one appreciates her and do mention things that you like bout her and don't tell her things like she has nice hair or lips ... write something that makes sense to her and something that she can relate to ... that's my opinion but ultimately its your decision .... good luck m8 and pls keep me posted on the development :P
...............................
A
reader, anonymous, writes (5 March 2010): It won't be a good idea to try to establish a connection before asking her out, anyway, because she's your boss, and there are way too many really nice looking people out there just waiting like wolves to make the next sexual harassment claim against someone, forcing them to lose their job for saying the smallest nice thing to them, or for being too nice. I know it will be hard to trust the odds that she'll go on even one date when she doesn't have the slightest idea of how you might be as a person, but better safe than sorry. Don't try flirting around with her or being too friendly at work, because way too many bitches will use that shit against you..read all about sexual harassment and how many people abuse the right to claim it AND get away with it. Even just going out with her can lead to you getting charged and her winning, if she wants to pretend something bad happened on the date, believe it or not...there are many stories..you would find it very interesting, just search for them.. Don't get me wrong, there are many worthy, decent, honest girls that don't do that, but how do you know she isn't one of them. That's not to mention having to work under her after you possibly break up, if you get together in the future. I don't mean to sound pessimistic but just to let you know what could very easily happen to you, as good of a person as you may be, if you're not careful about dating in the workplace. The safest route, if you have such a strong crush on her, is ask her out at an opportune time, and if she says no once, leave her alone even if she tries to flirt with you or show any signals. You'd be better off quitting your job and working somewhere else to chance asking her out twice after an initial rejection, even if she leads you on.. If she says yes the first time, go out with her and then take things slow...make sure you have her phone number after that, so you can have at least one way of communicating to ask her out a second time without ever having to be too personal at work and asking her there. Be smart at all times, and never let your guard down when you feel tempted to bullshit too much with her at work, because you WILL slip up and say something she can use against you as sexual harassment if she decides to. No hands on either, at work, EVER, and everything should go fine. You're better off feeling callous at work, toward her, than being 'a really nice guy' and getting fucked over by come cunt that set you up. She probably would never do that to you, but always remember to take those precautions anyway, no matter what, to save your own ass first and look out for number one. Just like there are alot of harassers out there, there are just as many half-brain mental cases out there just waiting to set up a good person to look like they're a harasser. I'm especially cautioning you because you label it as a crush on her, so it will be alot more tempting to fuck up, that way, if you're not always thinking.. Good luck, and hopefully she goes out with you, and hopefully she's never bad to you in that way.
...............................
|
