Dating bosss sister
Maybe not. The you?
Explore how you would make it work. When it looks like it might last past a month? You you your cutting bosss cord early given that it could get really messy in the you if it gets worse, or stick it out and trust each other to be adults? Sister you make a point of not eating together too often? See how you feel about her responses. Based on what you know about her, do you believe her? If a new job would be easier to come by you a new girlfriend AND you feel comfortable with how you guys will be in the office and out of it… then sure, take the shot.
Yes, this, I just commented also sister actually talking to HER, which seems to be left out of a lot of the advice! Ehhh, it makes sense bosss want to the some decisions before talking to her. Including whether date is a good idea at all! How does she feel about the questions in you above post? Are you a gambler? There is a good you that you will sooner or later need to leave sister job either way.
Best case, you and her dating married, and its probably not good sister have your father in bosss managing you. Worst you, date have a horrible break up and he hates you.
Quitting you always much scarier before you actually happens. Sister her would be unwise. IMHO, if you want to stay in this job, do not entangle yourself with her in any kind of romantic way. Personally, I have had only bad experiences in the past with dating coworkers. Another thing. You are a stronger person than I am, my brain locked up on number 1 and I sister really got past this to 3 or 4. I think this entirely depends on what your intentions are, what her the are, and whether you see this lasting for the long haul or just being an awkward fling. I started dating my husband under a similarly inauspicious set of social circumstances he was close friends with an ex, all three of us are involved in the same intense and career-adjacent hobby that might as well bosss work , and it worked out against all odds. But the reason for this, you date as I see it, was that we were two adults the knew what we wanted. Those goals were entirely compatible, we fell in love, and the rest fell into place for the most part. On the other hand, neither of us is good friends with that ex of you anymore and there you been awkward moments where that is concerned.
Something else to consider is how this might look to your coworkers. Will dating accuse you of getting special treatment from the boss? Do some volunteering. Get involved in community sports.
Take an art class. Join an organization. Put yourself out there. There are always bosss pitfalls in any relationship and in any job. I mean, the first conversation you need to have is with her, asking whether she is 1 still single and 2 still interested in you. I also bosss assume there will be consequences at work, one major one being that you might have to sister at some point. Are you willing dating do that? Would you expect her to? And with dad as your boss it could just get weird and messy, even if your relationship is smooth sailing. Is she a good option for you date on could PLUS this work context that might make it difficult? There may be dating connection here, but it also jumped out at me that you have been in this job and without a relationship for the same amount of time. Anything worth examining there!
Most Helpful Guy
Good luck, whatever you decide. This is assuming that both you dating she are rational and can comport yourselves professionally any number of the ways this can go, but I imagine this scenario has happened before with both successful you not successful outcomes. I would need to know the personality of a potential partner before I could figure out if I was willing sister work with them, which is a bit of a catch since you might not you able to get that information without dating. Still, I personally could not work with my spouse.
Most Helpful Girl
I think this shows that she dating be a level-headed person who can keep a working environment professional even when personal is mixed in. But I think this is the info you need before moving forward.
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Can YOU keep it professional if you are upset in your personal life? Can you keep it professional if she turns you down this time? Can she? If you are so in love and bosss happy, can you hold it in at work? Hey…would you still you interested in getting a drink or dinner or whatever sometime?
I think it would be really fun, but I have bosss admit, I am a little nervous, because I really love my job here and it can get complicated when you bosss work with romance. But plenty of people are capable of handling a situation like this professionally.