How To Ask A Coworker Out

How To Ask A Coworker Out

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The problem is that we work in a small corporate office (about 50 people), and everyone knows everyone else’s business. 
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This week, Doc Love, author of The System, advises a reader with that classic problem: a coworker crush.

Reader’s Question

Hey Doc,

I purchased “The System” a while back and haven’t been able to put it down since. I read it every day without fail and I thank you for coaching men like me to see the light.

Here’s my dilemma. A nice young lady, Jenni, started working at my company about six months ago. I noticed her giving me the eye here and there and finding reasons to walk past my desk, but she wouldn’t give me direct eye contact or she would say hello and walk by really fast, which showed me she had some interest but she was shy. Aside from that, we rarely bump into each other, but when we do I make it a point to speak up and keep things light, but she comes off as very nervous.

I’ve shielded my interest, as you advise in “The System”: “Go in slowly, stop, back up…” and that has worked! We have company meetings and at the last one I noticed that Jenni was trying to make eye contact with me but I got distracted by my boss. At the next meeting, which was today, she made it a point to sit near me and maneuvered things a bit so we wound up walking out together and making small talk. We discovered we have quite a bit in common!

The problem is that we work in a small corporate office (about 50 people), and everyone knows everyone else’s business. There were some people standing around us and I didn’t feel comfortable asking for her phone number in front of that crowd.

Due to a bad experience I don’t make it a habit to date my coworkers. However, I’m thinking of pulling out all the stops with this one. What are your thoughts about dating coworkers? Conservatively, I grade Jenni’s Interest Level in the low to mid 60s, and based on the way things went today, I think there’s a good chance it will grow.

I’m not blowing up Jenni’s email or sending instant messages every five minutes. I’m still playing it cool because we’re at work. And so I’m concerned about what my next steps should be. Should I keep playing it cool and get her phone number at the next opportunity, or let it go and move on to something less risky?

Thanks for your coaching!

Wellington — who feels like he’s on the right track

Doc Love’s Response

Hi Wellington,

First of all, thanks for the great compliment. And as a result of taking “The System” to heart, you haven’t made a mess of this thing with Jenni, which shows me that you’re not only reading my words, but you’re heeding them as well. Congratulations, my friend. You’re a smart guy. So far you’re doing a good job with Jenni. Keep doing what you’re doing. But you have to get this girl into a conversation.

Now, inside your small corporate office is where things get tricky. There are no doubt a whole bunch of other guys in the building who are after Jenni and want to take her out. And some of those guys are envious and they don’t want anyone to get her. So you have to be sure to keep your mouth shut in front of every other employee in the place. Like my cousin General Love says, “In this operation, you have to be as covert as a master spy.”
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