A
female
age
30-35,
anonymous
writes:Hi all!I've recently started a new position in my work place and since moving facilities my boss and I have become very close (he is the same age as me 26).It all started with him asking discreet questions about my relationship status, if I were against dating in the work place, how his position may get in the way of possibly dating someone as they may be worried about dating the boss...eventually I asked him if he wanted to meet for a very casual coffee. He agreed and when it got to the weekend I didn't hear from him so I continued my plans and didn't worry about it. The next week he apologised and asked me out for a drink after work which I couldn't do so we rearranged for coffee the following weekend. We spent hours talking, having a lot in common. We ended up kissing. Recently he took me on a second date, it was casual but fun and he took me out for one of my favourite meals which he remembered from some distant conversation we had. Of course we kissed again. Both times were very passionate but nothing more than kissing happened. I haven't felt such an electric energy with anyone like I do with him for a long time.However, my boss was very quick to delve into his own issues within what was primarily our first private conversation, which was when he asked me if I was seeing anyone etc...he admitted he was scared of being with someone for a few reasons, one was his heart condition which was very serious a few years back, his current family issues involving a critically ill step father, and that he just extremely busy with work/university/renovating his house/generally being independent. I was slightly taken aback by his readiness to offer such information but it didn't worry me.I am independent also, committed to my own career, so I understand him when he says this. I'm not a needy person and in a relationship I would say I am not worried about my guy having his own time for himself and his own social life etc. It is hard to put across the entire situation and how my boss has come across without writing an entire novel; I feel like he longs to be close to someone from everything he says and that he very scared, his parents and step parents situations as well as his own poor health in the past, have put him through some hard times. But he also wants to keep his independence and doesn't want anything serious.In all, I am totally confused and doubting if I should continue to see this man or not. He sends me mixed messages and I cannot read if he is perhaps a man who is scared of getting hurt or if he is just out for a bit of fun. I have had dealings with men who are around just for fun but I have also dealt with men who have made themselves out to be unavailable but we're actually scared to let someone in and that situation ended up being an extremely healthy and loving relationship.The boss issue doesn't phase either of us, we are both understanding that we keep it completely secret and are very good at keeping our distance in work. We are adult enough to not let anything interfere with our jobs no matter what the outcome. I'm just concerned about the relationship side of things here.If anyone could possible give me some advice on this kind of situation from experience or opinion I would be really grateful! Really sorry for the MASSIVE essay!!
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kissing, mixed messages, my boss Reply to this Question
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Fancy yourself as an agony aunt? Add your answer to this question! A
female
reader, aunt honesty  +, writes (2 March 2017):
 honestly I think this is the worst thing you could ever do. There should be a book on reasons why not to date the boss. Especially not when he is saying to you he only wants something casual. Whatever his reasons are that is still all he wants, and it sounds to me like you want more.
A
female
reader, Campari Milano +, writes (23 February 2017):
You seem to have your head screwed on! I would say, enjoy yourself. If you have found someone you have a connection with, that doesn't happen often.
Maybe it'll be more, maybe it won't. If you care enough to write about it; ENJOY YOURSELF!
You may get hurt, we all do. Only you can decide if it's worth it!
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A
female
reader, fishdish  +, writes (23 February 2017):
 Let me add, that I don't read this situation as "cool guy" or "sweet boss" but a man that shows he is sketchy and lacks understanding of boundaries. Red flag city.
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A
female
reader, fishdish +, writes (23 February 2017):
Do not get involved. He is telling you he is emotionally unavailable and if you cut it off now, no one (hopefully) is going to hold a grudge. Keep it professional or you risk the stability of your position. You will never be an equal in love or in work in this environment. It is better to just accept that you WORK there and nothing more, before people start throwing their weight around..
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A
female
reader, anonymous, writes (23 February 2017): You're an adult with sufficient discernment, so all the obvious risks, he's got them covered. One thing remained that he needed to get out of the way - his personal circumstances. Now he got that covered as well. If this turns out badly, which by all estimate, it would, he made sure it's on you. You knew ALL the risks. On the third date or so, you are digging your own grave. I hope you really wouldn't.
Love, M
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A
female
reader, mystiquek + ♥, writes (22 February 2017):
 Dating a co-worker is NEVER a good idea. Dating a boss? Pretty much career suicide within that establishment. I can't tell you strong enough...don't do it! Office romances rarely ever work out. Someone finds out, gossip starts, someone breaks up, someone gets hurt, someone either quits or gets fired and until then alot of unhappy bad vibes.
He's already made it clear he doesn't want anything serious. He is your boss. Keep your distance.
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A
reader, anonymous, writes (22 February 2017): As I know human nature; play with fire and you get burned.
As to keeping up your appearances (or covering your tracks) and maintaining professionalism at work; it takes encountering a real challenge before knowing how you'll respond to it. Millennials have a powerful sense of entitlement; and learn soon enough that what looks easy on the surface, is merely treachery lurking below. Experience is the greatest teacher of all!
I've managed a large corporate office for a number of years. Experience has taught me that most on-the-job romances, especially those involving the boss, crash and burn.
So many young people in their twenties believe they've got what it takes to have it all. The minute something goes wrong in these workplace-trysts; the tension in the room is so thick, you cut cut it with a knife.
As a business we have also endured some pretty messy scenes, and a couple of sexual-harassment cases. Which started as "office romances." Always between young people just fooling around; until someone stepped on someone's toes, or the office-gossip got back to them.
I don't advocate messing around with the boss. You will challenge his authority at the worst given time. Take his professional-reprimands or criticism of your job-performance too personally. Worst of all; if he turns out to be a jerk, seeing him everyday will make your skin crawl and your stomach will turn. How can he do your personal-review and performance assessments without bias? Another area you will be tempted to challenge, at the risk of exposure. Not to mention what some resentful or disgruntled co-worker can do, if your little secret is discovered.
Your precise description and expression of what's happening only shows you are the kind of person who is analytical and most likely to listen to good advice. You have a very good head on your shoulders, and I feel if anyone might pull this off. You can.
Keep your head about you, and stay grounded. Be very discreet, and if you happen see him openly flirting with another other female-employee; don't allow it to get to you.
The odds that may happen are pretty high, considering he was so bold in his attempt to getting to know you.
You're human, and your emotions will compel you to react if offended. That's the challenge of office-romances or dating co-workers. Maintaining self-control and avoiding giving away any signs you're seeing each other will become exhausting. Nosy busy-bodies make it their business to search for any signs of special treatment. They'll put two and two together. Then starts the gossip, and higher authority may come crashing down on him, for any apparent indiscretions. They bear the liability and can suffer enormous hits to their integrity and credibility as a business. Although you may feel it's none of their business.
Anything happening within their walls and involving their employees; is their business. They will make it their business. Small businesses are worse. They're quicker to fire, and prone to overstep proper protocols and by-pass labor laws. Right to hire laws give businesses lots of leverage over your fate.
If you are prepared to take on the worse-case scenarios if this doesn't work-out, enjoy it while it lasts.
I think he has already established his fail-safe exit-plan and given you all his caveats. He can bailout with little fallout or collateral-damage. You're already empathetic to is personal-issues, and think you have privy to his secrets.
Be cautious. There are two popular ways men gain undeserved-trust and gain the power to manipulate women. One is by sharing their secrets, and the other is by telling them he loves her. Two ways women destroy or manipulate men, is by being scorned by his betrayal; and exposing his secrets.
I don't mind writing massive essays, if they spread wisdom and save people.
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