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You Asked: Should I Worry About Dating My Boss?

DearSugar --

I work in a pretty small company, with people who are all between the ages of 24 and 40. A few months ago, my boss made a pass at me. I know that mixing business with pleasure is risky, but the thing is, I like him. He's smart, funny, cute and I now see why it's easy to fall for someone that you spend so much time with.

Most of us at work are single, and we'll go out for drinks or dinner together after work. My boss became more and more aggressive about wanting to go out on a date and finally I accepted. We have been together for about six weeks and it's been wonderful . . . until now. People at work have noticed we're dating and are starting to be mean to me. They think that I am dating him for perks and special treatment, but I am not; I genuinely like him and think I am falling in love with him. Should I feel guilty? -- Nervous Nancy

To see DEARSUGAR's answer,

Dear Nervous Nancy – I don’t think you should feel guilty one bit, but I do think you’d be wise to start updating your resume. I understand you’ve fallen for your boss, and I truly hope it’s a healthy and respectful relationship for you, Miss Nancy. I’m frankly a little bit nervous about the language you’ve used to describe this courtship (the "pass”, “more and more aggressive”), as from your note he sounds a little reckless or dominating. Please make sure you’re treated as peer outside the office, ok?

Rules against workplace romances between colleagues have changed over the years, but most businesses still have policies about bosses and direct reports, and for pretty good reasons. Besides, if there’s any collateral damage, you’ll pretty much feel the brunt of it, as you’re starting to see: the suspicion, negativity or jealousy of your colleagues; professional retaliation should you decide to end the relationship; all manner of heartbreak, awkwardness, and repercussion should he end the relationship.

I want this romance to be good for you, which means I really suggest you keep your eyes open, your head held high, and your business card in circulation.

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grl-in-the-world grl-in-the-world 8 years
This could get really messy with your co-workers. You could be accused of getting preferential treatment. And imagine the drama if you broke up! You don't need people gossiping behind your back, so if this is real then get out of there and get a new job ASAP!
Daisy6264 Daisy6264 9 years
Not a good idea to date your boss.
yiddidea yiddidea 9 years
My sister met her husband at work. He was her boss and as soon as they decided to start dating she transferred to a new job. They have been married for 4 years now. The #1 place to meet a spouse is in the workplace so it is inevitable that many people find themselves in this situation. Find a new job or transfer to a different department.
Marci Marci 9 years
I have the same advice as everyone else: Get another job. I had a situation where there was tremendous attraction with a higher up in a company I worked at. We had some lunches and talked at work, but once we realized it wasn't a passing flirtation, we knew one of us had to move. He had the stronger position in the company, so I got another job. We didn't marry, but stayed together for several years and I never regretted it. And yes: As cubadog said: If people have noticed it it's because you're not separating your profesionnal and personal lives.
Marci Marci 9 years
I have the same advice as everyone else: Get another job. I had a situation where there was tremendous attraction with a higher up in a company I worked at. We had some lunches and talked at work, but once we realized it wasn't a passing flirtation, we knew one of us had to move. He had the stronger position in the company, so I got another job. We didn't marry, but stayed together for several years and I never regretted it. And yes: As cubadog said: If people have noticed it it's because you're not separating your profesionnal and personal lives.
honeysugar28 honeysugar28 9 years
I wouldn't recommend this but if you both like each other its going to be awkword working toguether either way. You won't be able to hide your feelings so prepare for the whole office talking behind your back and rumors flying.
cubadog cubadog 9 years
This same issue was on here before. Get that resume updated and find a new job regardless of where the relationship is going. You don't mention how it got out that you two are dating and how either one of you has changed your behavior in the office since you started dating. Nothing should have changed and if people have noticed it is because you are not seperating your professional lives from your home lives.
kendalheart kendalheart 9 years
Yea there are only two outcomes I can think of fall in love and stay together or break up. So I agree with popgoestheworld maybe think about another work place to avoid any future problems.
popgoestheworld popgoestheworld 9 years
Most work places have policies against this and I'm very surprised yours doesn't. Start looking for a new job now. You'll either fall in love and then you won't want to work together, or you'll break up, and then, guess what?, you won't want to work togther. So better to get out now.
popgoestheworld popgoestheworld 9 years
Most work places have policies against this and I'm very surprised yours doesn't. Start looking for a new job now. You'll either fall in love and then you won't want to work together, or you'll break up, and then, guess what?, you won't want to work togther. So better to get out now.
Jinx Jinx 9 years
Of course you should be worried, for all the obvious (and happening) reasons.Keep dating, but get a new job.------------------------------------------------------I'm so happy cause today I've found my friends, They're in my head - Kurt
Jinx Jinx 9 years
Of course you should be worried, for all the obvious (and happening) reasons. Keep dating, but get a new job. ------------------------------------------------------ I'm so happy cause today I've found my friends, They're in my head - Kurt
getstinko getstinko 9 years
I think this is a bad idea, your boss should have waited to ask you out and not pressured you. that is the stuff that law suits are made of
getstinko getstinko 9 years
I think this is a bad idea, your boss should have waited to ask you out and not pressured you. that is the stuff that law suits are made of
Pinkgirl88 Pinkgirl88 9 years
I agree. I think its great to stay with him if you like him, but unless its your dream job and the only one you could have I would try to find a new job if you are serrious about himTINA!
Pinkgirl88 Pinkgirl88 9 years
I agree. I think its great to stay with him if you like him, but unless its your dream job and the only one you could have I would try to find a new job if you are serrious about him TINA!
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