How To Ask A Coworker Out

How To Ask A Coworker Out

"The problem is that we work in a small corporate office (about 50 people), and everyone knows everyone else’s business. "


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.


What you should have done when you were in the crowd after the meeting was pulled Jenni over several feet to the side and said, “Here, I want to show you something.” And at that point you should have closed and asked for her phone number. But not if the other people could overhear you. You don’t want them catching on to anything, guy. If you’d drawn Jenni far enough away and gotten her digits, your office mates would have only seen your back and not what you were writing down. So next time that’s what you have to do.

What are my thoughts on dating coworkers? No. 1, it’s very dangerous because everyone in your office has a big mouth and nobody can keep a secret. Secondly, you have to remember that if it doesn’t work out, it could very well get messy. Because two things happen in a relationship: you get married or you break up. Most of the time you’re going to break up. And if you break up with Jenni, remember that you’re going to have to see her, she might talk to the boss about what happened, the boss might side with her, etc. There are any number of scenarios here, and none are good.

Like my Uncle Jethro Love says, “You’re really opening up a can of worms here, boy.” So what you have to do is keep playing it cool, but when you get Jenni alone again, get her phone number! But you have to do everything on the sly in order to avoid complications. Remember, you’re working with a whole bunch of other people and half of them want to take Jenni out themselves, and they’d love to find out about what you’re up to so they can undermine you. Not to mention that everyone loves to gossip about what’s going on in the office as it is. A dating relationship right under their noses just adds fuel to the fire.

You can try to estimate Jenni’s interest all you want, but you don’t really know what it is because you didn’t ask for her phone number. To you psych majors, nothing starts until you ask for the phone number. So you’re getting a little bit ahead of yourself here, buddy.

You shouldn’t be sending Jenni any emails or text messages at all. You should be strictly business with her. But you definitely should get her phone number at the next opportunity. 

Just remember that if you go out with Jenni and break up with her, you have to see her all the time. And in a small office, someone is going to sense what happened between you. Above all, you don’t want your boss to sense it because if you get married to a girl at work it’s OK, but when you break up with her, it isn’t okay. The head honcho is going to know that there’s friction between the two of you, and that isn’t good for business.

Remember, guys: When you hustle a girl at work, you have to be extremely cautious.


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