Tbickle76 Posted January 4, 2007 Posted January 4, 2007 I’m in a particularly unique situation, A few years ago I was in college and my best friend was working. He was good friends with his boss and so occasionally his boss would come out drinking with us and soon I became real good friends with him as well. Once I graduated I needed a regular labor job to have while I pursued my career on the side. I asked my friend’s boss if I could work for him and he hired me on the spot. Since we’ve known each other for about a year before I started working for him, we consider each other more as friends rather than boss and employee. Occasionally his sister would come out drinking with us and I’ve gotten to know her pretty well too. We always hit it off really well, always have a great time together, and I’ve recently found myself flirting with her a little. Right now we’re just friends but I think there’s an underlying attraction going on between us. One of my friends who was out with us one night told me it was pretty obvious we liked each other, so I know it’s not just me. The thing is I’m 23 and my best guess is that she’s 30 give or take. She’s also my friend/boss’s sister. My boss is really cool, he knows I’m a nice guy, and he knows I don’t plan on working for him forever, but I’m still worried about what he’d think of me dating his sister. I know I should talk to him about it but how do I bring up this issue easily. Normally under these circumstances I’d leave it alone but I can’t stop thinking about her. I really like her a lot. Any advice?
Valentine Posted January 4, 2007 Posted January 4, 2007 Ask your boss's sis if she likes you or not. And for ask i don't mean: "Hey i like you do you like me?" Try doing it slowly. The first thing you will need is the truth, cuz what if it turns out she doesn't like you? After you know that you like each other, dont mention it to your boss. He will know in good time. Main point: Just let it all be [ worked for me, prolly will work for you]
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