Dating A Coworker. Good or Bad Idea?

How to know when dating a coworker is a good or bad idea and how to approach it.

In this video coaching newsletter, I discuss an email from a viewer who thinks he is having a love at first sight moment with a coworker of his. From his email, you can tell he’s reading way more into things than there is evidence that she feels the same way. He can’t approach her directly, because if it doesn’t work out it could blow a good business relationship and, potentially, future business for him.

He’s trying to fly under the radar, because there does seem to be some interest on her part, but he must be very tactful and indirect if he is to succeed and create the conditions where her attraction will grow. My comments are in bold italics like this below in the body of his email.

What’s interesting is, if you’re a man in today’s world, you have to be very tactful about how you handle things, especially when you notice that somebody you work with is attracted to you. And in this case, you could tell he’s kind of projecting his high interest and putting this woman on a pedestal, but there does seem to be some reciprocation on her part that she’s interested. And so, obviously, he’s got to approach this very tactfully, because as he states his email, he wants to make sure that he doesn’t screw up the business relationship he has with the company she works for, because he’s hoping to get a bunch of future work potentially down the road.

So, what happens if you’re a guy in the modern world, and you have a female coworker and you could tell that she likes you? How do you approach those things? I figure this is a good email, because I’ve had plenty of experience with this in my life — back in the day when I worked with other people, and obviously, working for myself and having a business.

Especially when I was in real estate, I had a lot of women that worked for me. I had the experience multiple times over the years where they would come and knock on the door, “Hey, can I talk to you for a second?” And then they come in, shut the door, want to sit down and basically tell me that they’re in love with me or they think we’d be perfect together. Sometimes, they had just decided to leave their husband, or they had split up or their boyfriend, and they’re thinking that they can basically come in and tell me all the things that we have in common.

In my position, I always tried to not encourage those things. And the reality is, when you try to not encourage those things, especially with a woman that likes you, it actually causes her to go out of her way more to show you that she’s interested. So, you have to be very tactful in how you approach those things.

Viewer’s Email:

Hey Coach,

I recently started seeing a new coworker outside of work. I always try to follow your advice when dating new women, but this one threw me for a loop. About a month ago I met this amazing woman in a business meeting. It was one of those “love at first sight” kinda things. 

Slow your roll.

She’s an interior designer, and her company hired me, a photographer, to take photos of a building she designed. In the meeting, she mentioned she liked photography and did it in her spare time. We had a couple other back and forths, and it was clear that me and this girl were connecting. But I took your advice and didn’t seek her out after the meeting.

Yeah, that’s the thing, when you understand “How To Be A 3% Man,” you can tell when women are into you and attracted to you and when they’re not. And so, if it’s somebody you work with, somebody that works for you — or like in this case, he’s kind of like an independent contractor, but he doesn’t want to screw up his business relationship — things have to be casual. Especially doing group things with your other coworkers.

Say everybody goes to happy hour together. You don’t go and try to sit next to her at happy hour. You go sit where you want to sit, and over the course of the evening, you’re laughing and joking with everybody. Whether it’s an old lady, or a young attractive woman, or the guys that you work with, everybody kind of busts each other’s balls in a good-natured, playful kind of way.

I’m like that with everybody. I like to have a good time, I like to have fun, and I don’t like to be too serious. And humor communicates that you don’t really take yourself too seriously, or life, and it puts everybody at ease. And also, humor is a sign of a high IQ and high intelligence, so it’s obviously very attractive to women.

The idea is you’re hanging out in a group setting, and if a woman likes you, at some point she’s going to make her way over to sit next to you and start bumping into you or touching your arm. Women just do these things subconsciously — playing with her hair when she’s next to you, asking you personal questions, looking deeply into your eyes and smiling. I mean, when you get good at what’s in “How To Be A 3% Man” and you’re in enough situations, you’re going to feel it. You’re going to recognize it.

And all you can really do when you see that is you can gently invite, because a man’s job is simply to extend the invitation. Because in my experience in the business world, especially back when I was in real estate, you start out with a big group at happy hour and the group usually shrinks. And then, 10, 11 o’clock at night, there might only be three or four, four or five of you hanging out, and things just kind of happen that way. And you say, “Hey, you want to go out, or go grab a drink somewhere else, or go shoot some darts or whatever,” and things just naturally progress.

What’s amazing about it is that it’s your indifference and your inaction that actually makes you more attractive. Because as she displays ever increasing signs of her romantic interest, you’re completely indifferent to it. You’re not trying to get her number and go out on a date or anything like that. You’re just enjoying hanging out together. And, therefore, when you don’t try to hit on her, and you don’t try to seduce her, and she likes you, and you’re you’re treating her like you treat everybody else, she’ll actually become more aggressive.

She goes out of her way to get your attention more, and then it’s just a matter of inviting her to continue joining you. And if she’s touching you and she’s got her hands all over you, I mean, at some point later in the evening, you say, “Well, you’re touching me so much, maybe you should just get it over with and kiss me.” And if everybody’s having a good time, if she’s showing all the signs, nine times out of ten, she’ll make a move.

Well… for about 3 weeks. I needed a second photographer for a project and figured it could be the “in” I needed with her, without ruining the new relationship I had with her firm. 

So, he’s got to kind of be indirect about it and be very tactful. Because he noticed there was interest here, or he believed there was interest, and from his email, once we get a little further into it, you could see there’s some interest there. But you could tell the way he’s looking at it, he’s like, “I found the one.” But that kind of mindset can get you into trouble, especially in a situation like this.

So, I found her on Facebook, told her I needed a second shooter, and said if she was interested I would love to meet for a drink and share the details. And before I ended the message I asked, “When are you free?”

He’s kind of presupposing she’s going to be interested, because she did say she was interested in photography. And so, three weeks had gone by. It’s interesting, because women are always testing the safety, the strength of a man, “What can he provide? What kind of conditions can he create?” Because a guy who’s a needy, insecure jackass is going to be really aggressive and get upset if she doesn’t reply right away. So, notice what happens.

I didn’t hear back for a couple days but eventually got a reply saying she WAS interested, and I set a time and location right there.  We met up at a small bar, had a good time, and at the end she asked if we could text instead of using FB Messenger.

So, now she’s asking for his number.

I gave her my number, she texted me hers, and before I left, I scheduled our photo shoot for the following week. I didn’t text her the entire week, and she showed up on time, (good sign).

Well, at the end of the day, it’s business. So, if you’re making a business appointment, you would hope that she would keep it.

We had another great time together taking photos of landmarks around our town and getting to know each other between locations. When we were finished taking photos, she asks if I wanted to grab a drink, (BINGO!).

So, now she’s asking to spend more time. And so, he’s doing a good job of just kind of, hey, this is a photo shoot. Because think about it from this perspective, if this guy’s used to having women like him and come on to him, he’s not going to be in a rush. He already has all the feminine energy in his life that he needs. Why does he need more of it? It’s always welcome, but he’s not trying to make it happen.

A guy with no game is going to be trying extra hard to make something happen. But because of this business relationship and this specific type of situation, he’s got to be extremely tactful and allow her to come to him. So, he’s creating the conditions where it’s work related, and then they can have a good time together and joke around and be playful. And because she feels safe and notices that he’s not trying to do anything, his inaction actually makes him more attractive. “Why is he not hitting on me? Does he not like me? We have such great chemistry. We’re both into photography.”

On the inside, I’m jumping for joy thinking, “This is exactly what I wanted!” But on the outside, I’m James fucking Bond. I said yes, and we hung out for a couple more hours. At the end of the night, I drove her back to her car without bringing up getting together again. When we got there, she kept finding excuses to linger, (double checking she had everything, thanking me for the drink, etc.), but I held strong and didn’t bring up hanging out again.

Well, this is obviously the moment where you’re going to go for the kiss. But unless she’s standing extra close, touching your arm and the signs are really there, it’s best to do nothing, because again, you don’t want to blow the business relationship, especially if you were wrong. Maybe you misread her.

I’m confident I could get another date with her.

Well, it wasn’t really a date, dude. It was a business type of thing. But now you’ve created the conditions where you show that it was totally safe, and now the ball’s kind of in her court. Because now she has your number, and then if you just disappear and let a couple of weeks go by, she might reach out and go, “Hey, how did the photos turn out?” or “How did the shoot turn out? What did the client think of the pictures we took?”

But on one hand, I have to meet with her regularly for work for at least the next month.

Then, quite frankly, I wouldn’t do anything. I wouldn’t do any kind of pursuing or reaching out, just because of this specific type of situation, because you have to be tactful. And you want to create the conditions where she’s like, “Why is he not do anything? Why is he not hitting on me? Does he have a girlfriend? Does he sleep with somebody else? Does he not find me attractive?” These are the kinds of things that go through a woman’s mind when she’s interested, and she can kind of tell the guy seems to be interested and they get along well, but he’s not doing anything.

And there’s a chance it could turn into a long-term business deal.  On the other hand, I wanna wait 5 days and call her to hang out, have fun and hook up.

In this particular case, I would advise against that, because you’re going to see her several times over the next month, and if you’re going to make a move on her, you want to be absolutely certain that you’re not going to get rejected and blow it. Because if you do make the move and you misread the situation and it blows up in your face, now you jeopardize your business relationship. So from that, there’s just too much downside risk.

And that’s what happens sometimes. You’ve got specific cases here, you’ve got to be totally indirect and just chillax. Create the conditions where she becomes more aggressive. Because again, think about from this perspective, what if you already had a couple of girlfriends or a couple of women you were dating in your rotation, you were very happy with. Or maybe you were seeing somebody you really liked and were thinking it’s going to go somewhere, you’re not going to be thinking like this. You’re not going to be thinking, “Hey, I want to get together and make a date or go have another drink,” or whatever.

When you see her you’re just going to be like, “Hey, nice to see you,” and see how she is towards you. See if she starts texting you. And if she starts texting you, then you say, “Hey, why don’t we meet up for a drink and hang out and catch up? I’d love to see you.” Say it just like that. It’s still innocuous. And then, usually what happens is she becomes more aggressive the next time you’re together.

So, again, you have to be tactful. Because I’ve had a lot of experience over here. Especially when you’re in a position of power, like I was in real estate, where I was on TV, we had all these people working for us, a lot of high achievers, a lot of good looking dudes, a lot of good looking girls. I knew a lot of people in the industry, so there were always people around, there were always women around. Women become aggressive in these situations. And it’s a nice place to be as a man, because you don’t really have to do much. It just kind of happens, and you just allow these things to happen.

So, my question is, will dating this unbelievable woman AND communicating with her weekly for work derail the proper way to court her over the next 7-8 weeks?

Well, again, I wouldn’t be trying to put out all the rules and trying to be a robot, because you have to be tactful here. You’re going to see her anyway, therefore, there’s no reason. I mean, you’ve got to treat all women the same. I’m always the same with everybody. I’m always a jokester and goofing around and breaking people’s balls.

If you watch any of the podcasts, it doesn’t matter whether it’s Gracie, or Jen, or my Aunt Charlene, or Andy, or Mike, it’s like, I fuck with everybody. I’m always joking around with everybody. It’s just the way I am. We like to have a good time. I work with people and I have good friends that we all have a good time with. And so, that’s the way you want to be with all people, because that makes it easy for you to meet new people and to make friends and for you to be likable and to be safe.

Even when I’m around kids, it’s the same way. Kids like to joke around and you’re going to tease and be playful with kids, and it makes everybody feel safe. And that’s the best vibe to be. If you’re in sales, same thing. If you can make people laugh and smile and feel good, it’s going to create rapport. And everybody loves people that make them feel good about themselves and that are easygoing, easy to be around. And you should always be that way.

If you’re in line at a grocery store and there’s a 70-year old lady, you should be joking around and teasing her and her husband, just being playful, and making jokes, and making light of situations. It puts everybody at ease. When you’re this way with everybody, everywhere you go, you’re not attached to anything. You’re not trying to force anything. Like I said, it makes everybody feel at ease that they can really be who they are around you and safe to express that.

And like I said, when you encounter women that are attracted to you, they will reveal their attraction, especially when you don’t do anything about it. Your inaction is what makes you more attractive. Your indifference to noticing that they’re attracted to you. It’s the best way to be.

This one’s a keeper, Coach, and I appreciate your advice.

Bob

Well, as far as her being a keeper, you don’t know that. You just don’t know. Yeah, you hung out with her for a little bit. Yeah, you’re attracted to her, obviously, really attracted to her. It seems like she’s attracted to you, but, she’s not jumping out of her skin to spend time with you. And so, since you’re already going to see her over the next month or so anyway, I wouldn’t do anything. I wouldn’t ask her to hang out again.

Just see what happens the next time you get together with her, because you might notice she’s a lot friendlier next time you get together, or she might be a little more reserved because she’s with her coworkers. You just you don’t know what you don’t know. And when you leave, you should always say, “Hey, shoot me a text if you’re if you’re around, if you want to grab a drink or whatever. I’d love to catch up.” You just say it like that.

It’s like, you could throw the invitation out there, but you’re not going to try to set a date, because she already has your number and she might text you. You just hung out with her, so she might text you in the future if you haven’t talked in a couple of weeks. Like I said, it’s always best to throw it out there in the form of, “Hey, let’s go hang out,” especially in a group.

Because if you’re indifferent, you’re not trying to make anything happen, you’re treating everybody the same, you’re treating all the women that you’re hanging out with the same. And the ones that really like you — just like I talked about what my experience was when I was in real estate, you get a not get a knock at the door, “Hey, you got a few minutes?” and they come in — they make their move on you. Or when you’re out together, everybody’s having a good time, women become very aggressive and become the aggressor.

But like I said, this is a special case, and this is different than what’s in the book, because you’ve got to be tactful. Otherwise, it can blow up in your face and cause you to lose your job, and in this guy’s particular case, lose business. So, that’s the best way to handle this situation.

So, if you’ve got a question or a challenge and you’d like to get my help, go to UnderstandingRelationships.com, click the Products tab at the top of your screen and book a coaching session with yours truly.

“Attraction is not a choice. It’s either there, or it’s not. Attraction is not created but revealed. Mother nature takes care of attraction, and it’s therefore innate. Love is allowing. Feminine attraction grows towards the masculine when it feels safe and comfortable enough to grow or not to grow. Masculine energy makes it safe for feminine energy to flourish. You can’t force a rose to grow and blossom any faster than it is ready to. You can only create the conditions where it grows at its own pace.” ~ Coach Corey Wayne

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