[Anonymous]

Ok here’s the short version, hoping to get some feed back as I believe I only have one shot at this—

I am 30 she is 40. We have been friends for 4 years. We flirt off/on for four years. Both of us were in separate relationships and both talked to each other for advice. I been there for her and vice versa. Both of us are now single and hang out as friends about 2 weekends a month. There has never been anything romantic that has gone on, although both of us have sent signals at one point in time.

I now own my own business where she has become an employee in. IF I go to make a move and it’s rejected it will be very bad for business. She also considers herself a cougar and sometimes she talks about settling down but sometimes she talks about wanting to go on the run. We have a natural friendship but I think it will be better if we were tied together for a bit to see what happens.

How do i make this move without it interfering with my business? As I said i dont 100% know if she will want to move on to the next level but i find myself thinking of her alot lately. If i do make a move and it’s turned down it will hurt my business dramatically and my standing as “boss”.

Any advice is appreciated.

[Ask April Masini]

The best way to date an employee is to keep things very clean — in other words, don’t mix business and pleasure. It’s crazy for people not to date people they work with because since people spend so much time at work it’s very normal to meet attractive singles there. What I suggest is that when you ask her out you do it on non-company time. Don’t use your office e-mail or cell phone for socializing if possible. And keep the lines of communication very clear. As her boss, you run the risk of things go badly socially and she feeling that her business position is compromised as a result of your personal feelings for her — so avoid that scenario at all costs.

I hope that helps. Let me know how things go.

And join me on Facebook! Here’s the link for AskApril.com on Facebook: [url][/url]. 😀

[Anonymous]

[quote=”April Masini”]The best way to date an employee is to keep things very clean — in other words, don’t mix business and pleasure. It’s crazy for people not to date people they work with because since people spend so much time at work it’s very normal to meet attractive singles there. What I suggest is that when you ask her out you do it on non-company time. Don’t use your office e-mail or cell phone for socializing if possible. And keep the lines of communication very clear. As her boss, you run the risk of things go badly socially and she feeling that her business position is compromised as a result of your personal feelings for her — so avoid that scenario at all costs.

I hope that helps. Let me know how things go.

And join me on Facebook! Here’s the link for AskApril.com on Facebook: [url][/url]. 😀[/quote]

I hung out with her Saturday with several of our mutual friends. We were flirting but at one point she tried to make me jealous by saying another guy was calling her and had to take the call. My other friend saw her phone and said it was her room mate calling her. I am assuming this is all a game, and now I am wondering if she is trying to test me.

Obviously there has to be something there when we hang out on non-work related weekends.

I am going to make my move this week, the only thing stopping me is that if she says no, my business can be ruined and it will kill the friendship entirely. And if my business is ruined it will kill profits and everything, so that is why it is risky and I haev to make sure if the answer is no, that my business won’t suffer.

[Ask April Masini]

It sounds like this relationship is too risky to broach and therefore, you shouldn’t ask her out.

You asked me how to make a move on an employee without hurting your business — but then you write: [i]If i do make a move and it’s turned down it will hurt my business dramatically and my standing as “boss”.[/i]

It sounds like you have too much to lose. Wait until you’re not in such a risky situation or she no longer works for you and then ask her out. In the meantime, date other women to take your mind off of her.

I hope that helps — and don’t forget to join me on Facebook. I didn’t see you there! 🙁 Here’s the link where you can request free membership: [url][/url]. 😀

[Anonymous]

Update:
We hung out tonight for 8 hours or so at a local bar, no job stuff. We made out before we split ways, but before it could go to the next level, she said I was the best male in her life and didn’t want to ruin this. I told her if anything worth having it’s worth having. She said she wasn’t sure and wanted to revisit this issue.

When I got home I got a call and we decided we are going to take it slow and keep it between us. If we feel we are really bonding, we will be open about it in a few months. There are alot of people in our business, both employees & competitors who could ruin us if it got out, especially if it was just a fling, so we are going to take it really slow and really private.

So i guess for anyone else in this situation, just take the person to a bar and if the person is into you she will hang with you, if she isn’t she wouldnt’ even be there. Am I safe to assume that? The only thing April that scared me was that she said I was the most important male in her life and her best friend, so I just 100% hope it works, as she is my best female friend (but not my best friend, as she doesn’t have many close relationships with friends as i do) and obviously don’t want our friendship which is amazing to be strained at all, but I also feel that if we connect like this we haev to at least take a shot rather than wasting more time in life.

[Ask April Masini]

I’m happy for you that things are moving in a good direction. Please be sure to re-read your posts because you are all over the map, emotionally. You want to date her, but then you’re afraid this will put your business in peril. You need to make sure you balance your emotions and those matters of the heart and other parts south of the heart 😆 with your brain power.

Again, keep your side of the street clean and be respectful of your business vs. personal relationships.

Receive her compliment that you’re the most important man in her life as a big, fat compliment and enjoy it rather than be scared by it. 😕 Be the best date and boyfriend you can, and at the same time, buckle up knowing that relationships NATURALLY have bumps in the road, and yours with her will be extra dynamic because of your personal and business lives together. This is NOT a bad thing at all — in fact MOST people date where they work because they spend so much of their lives at the office, that’s where they meet other singles. But you do have maintain balance and integrity.

Let me know how it goes — AND JOIN ME!! on Facebook at this link: [url][/url]. I want to have you as a member! 😀

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