Workplace crush

Dear Shawn Mackenzi,

Thank you in advance for choosing my letter! I really need your help! I am totally into with a woman at my job. Well, she doesn’t actually work with me; she works with the business across the hall.

I see her every day and have even had brief conversations with her on the elevators, but have never got up the nerve to ask her out. I’m an attractive guy, so I don’t foresee her turning me down but just don’t want to screw up by asking the wrong thing.

Now, I will throw in there that I may have a bit of a reputation around the office as a playboy because I’ve dated quite a few women in the building, but I really like this one. She’s smart, beautiful and sexy…all the things I would look for in a woman for a more serious relationship. How can I approach her and ask her out without her thinking I’m just out to get in her pants?

“Tongue Tied Playboy”


Dear Tongue Tied Playboy,

Thank you for sending in your letter. It seems you’ve gotten yourself into quite a predicament, and by your own actions I see. Well, we all make mistakes, but I have to be honest with you, you’re going to have your work cut out for you if you want to change public opinion.

Your musings with “quite a few” women in your building have sent a strong message that ladies can hear loud and clear, and that message says “I’m only interested in hooking up.”

If you want to show the woman across the hall that you are serious about building a relationship with her, I would start by being honest and upfront about the relationships you’ve had with the other women in the building.

This wouldn’t be my normal recommendation, but your “playboy” reputation is such that either she already knows your history and wants to run far away from you; she doesn’t know yet; or will find out later on which will ruin any relationship you do build with her. I say yet because trust me, women are a part of a special club, and if there’s a shady guy in the building that should be avoided, she will know. The e-mail chain is probably already in her inbox, so be upfront about it.

Second, find things about her that you like that goes beyond the physical. I understand completely that men are visual beings, but aside from this woman’s beauty, sex appeal, and smarts, what do you find alluring about her?

I can tell by your letter that you are very self assured, and while women like confident men, they don’t like cocky ones. If you approach a woman in a way that makes her feel like you’re “gaming” her, she will know it and you will lose, so don’t try it! Let your intentions be honest and pure; continue to build a friendship by asking her to a casual lunch with a group of co-workers.

I suggest this approach because your reputation needs to be reformed my friend. If you really want to get to know her, you will have to start slow, and a lunch “date” with friends is a good start. Remember, women are watching. They will take notice that your behavior has changed, and will come to trust you as the playboy you are no longer.

Like I said earlier, you’ve gotten yourself into quite a predicament, but it’s not one you can’t get yourself out of. Take it slow, and decide if she’s really someone you want to be with. Don’t play games with her because I will find out and come get you (smile)!


Shawn Mackenzi

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