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I have a crush on my boss and don't want to regret not telling her

Tagged as: Crushes<< Previous question   Next question >>
Question - (27 September 2014) 5 Answers - (Newest, 28 September 2014)
A male United States age 41-50, anonymous writes:

I'm 39 and my boss (owner) is 44. I have been at my job for 5 yrs and I have had a crush on her ever since, she has not dated anyone in the time I have been there, it breaks my heart knowing she goes home by herself and eats dinner or watches tv by herself, her daughters and granddaughter have moved away, so she is very lonely, I want to so badly be there and make her dinner, listen to her about her day, rub her feet and have her fall a sleep next to me, part of me wants to tell her how beautiful she is and how when she laughs I giggle, I need to tell her before I regret not saying anything

View related questions: crush, crush on my boss, my boss

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A reader, anonymous, writes (28 September 2014):

The only problem with this is that you two work together so if it doesn't work out it could become a problem. I would definitely ask her out and see how things go though, before telling her about all of your feelings, that can come later on.

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A male reader, anonymous, writes (27 September 2014):

Tell her but subtly, start talking about films and ask her her favourite type of film, say to her when was the last time someone took you out for dinner and a movie......then ask her, the key is that if you end up not working out don't be strange with her.

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A female reader, Honeypie United States +, writes (27 September 2014):

Honeypie agony auntHave you thought about asking her out, before declaring your feelings for her?

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A female reader, anonymous, writes (27 September 2014):

Yeah tell her, don't come on too strong (so don't announce how you want to be falling asleep next to her etc...) but just ask her if she would like to join you for dinner one evening?

If it goes well, well then to out a bit more. Just take things easy and let her see how she feels about it too.

Best of luck, be yourself and get to know her on a personal level and fingers crossed things work out :-)

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A reader, anonymous, writes (27 September 2014):

Of course you need to tell her. Anyone who is loved deserves to know. What she decides is her call but to feel loved never hurts. Just tell her once and then let her make up her mind.

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