[Ben]

April et al,

I own my own small business and I hired a woman about a year ago as one of my main employees part time. She was my very first employee, and we spent hundreds of hours together one-on-one, doing work and growing the business. It is now successful and profitable, but she has chosen to leave to go to graduate school. She also got offered a part time job more closely aligned with her graduate studies (and better paying) than the job she had with me.

At first, I wasn’t at all attracted to her. I knew she would be very professional, but she came across as stiff and a little aloof. We’ve since joked about this, as she says she’s heard this before.

After spending so much time with her though, I feel like this has grown into more than just a crush. I just adore her – think she has an amazing brain (we are a small school and she is rarely stumped by any of the math work we need to do no matter how advanced). She’s very funny and can do a good Sean Connery impression among others. It seems we never run out of interesting things to talk about – whether it be religion, politics, friends or other ideas.

I have hesitated to do anything because she worked for me, but she has recently left the position, but gave me plenty of advance warning and also told me she “would not disappear.”

I feel like when she worked for me she flirted up a storm – walking into my office to eat chips out of a bag of in the middle of my lunch, or saying at one point that “she was a sap” because I didn’t say goodbye to her when I left. (She called me 15 mins after I left to say this).

I will try to buy your book, but I think I know a fair bit about body language. When were alone in my office, she often gazed at me directly and for long periods, and often played with her hair and holds it above her shoulders behind her head. She also seems to notice small things about my wardrobe (like what kind of shoe covers I had on when it snowed). More recently, she took the time to clear snow off my car in the middle of a cold, snowy evening when she left a few minutes before I did.

What complicates matters is that I have been finalizing terms of a divorce and she’s met my soon to be ex. It is very low drama – and my separation started long ago, but I am not fully divorced yet, but my ex knows I am dating and is fine with it.

When this woman went to a few weddings this past summer I mentioned how many opportunities she might have to met guys – and she immediately dismissed this in a friendly way saying she already knew all of them.

I did ask her a while back (about 7 mos ago) if she wanted a tour of some parts of the city as she was/is relatively new to the area. She said she was busy and had to study.

Now that she’s no longer an employee, I feel like it would be okay to ask her out. I have decided to have a sendoff party for her and she’s said she’s free. I still don’t know if she likes me, and she seems really shy about saying anything herself – I think more than anything because it wouldn’t be professional. I do have other female employees, but I don’t get this same feeling – with my other employees – especially one woman who has been around for almost the same length of time, I feel like it is totally platonic – not flirting at all is going on. They are friendly, but not overly so.

This woman is really one of the most interesting, fun and amazing women I’ve met in a long time. I thought about writing her an email to express my feelings as that might take some of the awkwardness out of an in person situation. My experience though is that if a guy shows his cards up front by just saying how he feels in writing or in person it often takes the mystery out of the situation, which is one main parts of attraction. Any advice would be great.

Thanks,
Ben

[April Masini, your AskApril]

She definitely likes you, but the real obstacle here is that you’re still married. 😮 Get divorced. Make it final. And then ask her out on a date. I know you think your divorce is low key and drama free, but I would advise you not to talk to your wife about your dates. You never know what can inspire a spouse to go ballistic on the divorce terms, but since you’re still married, you should hedge your bets and lie low until you are divorced. And…. if there are children involved, continue to play your dating life low key. Custody is always an issue and any agreement is subject to modification for any reason. So take care of business, and then ask her out. I think she’ll say yes. 😉

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