She Seems Interested, But I’m Her Boss. How Should I Proceed?

A low risk way to date a coworker who seems interested in you.

In this video coaching newsletter I discuss an email from a viewer who is almost 40 and has been following me for 7 years and listened to the audiobook countless times. A woman who works under him seems attracted and interested. However, he doesn’t want to risk his job if he’s misread the situation and asks the best way to approach it. My comments are in bold italics like this below in the body of his email.

Hi, I’m Coach Corey Wayne, and this is my Video Coaching Newsletter. And the topic of today’s Members Only Newsletter is, “She Seems Interested, But I’m Her Boss. How Should I Proceed?”

Well, this particular emails from a guy, he’s almost 40. He’s been following me for seven years, says he’s listening to the Audiobook countless times. And he says he’s got a woman that works underneath him and is attracted interest. I guess they’ve been working together for two years. And so he doesn’t want to risk his job if he’s misread the situation. So I suspect just because this email, I mean, somebody that’s been through The Book 40 times, and is kind of asking these questions tells me they probably haven’t practiced it a lot because I do talk about these issues quite often.

But it’s a good email, because these things, if you work in business, you work in the corporate world, these things are going to happen. And when you look at statistics and how most people meet, the top two are work and social circle. In other words, you get introduced through other mutual people or mutual friends that you know or mutual acquaintances. So it’s important if you’re going to shoot your shot, especially if you work in the office. In this case, you’re the boss, that you create the conditions where she comes on to you and she makes it so obvious, especially like in this case, if she’s like texting him at night or on the weekends when he’s not at work, that would be more ideal.

Because you can see as we go through his email, he’s created the conditions where when they’re at work, she’ll be texting them at work, but he doesn’t really say if they’re talking outside of work, because oftentimes in these cases, what I usually recommend is if you got a girl that you think is interested in, you do like a group, you know, a company happy hour with several people, her and other girls, some of the other guys and just all go and do something and then see what happens.

You got a big table together, does she sit next to you? Does she sit across from you? Does she engage you in conversation, or does she stay far away? Like she doesn’t want to be involved at all? Because women who like you are going to put themselves in your orbit. They’re going to get near you. They’re going to sit next to you. They’re going to come up with reasons to touch you or bump your arm or stand extra close.

And as the evening progresses and then people start to leave and go home, she’ll be the last one to leave. And then it’s just the two of you. Because when women like you, they help you. They put themselves into your orbit. And so in this case, which where you’re the boss, you got to make sure you’re tactful about it, and you create the conditions where she can make it obvious that she likes you.

Viewer Email:

Hey Coach,

Quick background about me. I’m just shy of 40 & been following you since 2019 and listened to 3% Man, countless times. I’m blessed to be tall, good-looking, confident, and funny. Attracting women has never been a challenge. I rarely get nervous around beautiful women (or anyone, really), and I’m currently an executive leading a sales division. I met this woman a little over two years ago when I started a new job. She’s a solid 10. Stunning, classy, mysterious, and I actually met her during the interview process.

My first instinct was to flirt (and I did), she laughed, and I picked up clear signs of mutual attraction. But after that first encounter, the next time I saw her, I was her boss. I decided not to cross that line. I didn’t know her yet, didn’t want to risk my position, and made no move. Still, she opened doors—texting me, offering to help with anything I needed, sending memes, asking deep, date-style questions, checking on me after work, offering to show me around. Eventually, those invitations faded as I showed no interest.

Well, in that case, if she’s at least then if she was making it obvious. Especially if she’s texting you outside of work and is sending you memes and it’s not talking about anything business related, that’s typically what they do. Again, they’ll tend to linger. Just like girls at the gym that like you, will come and linger around the machines you’re using. Even if they were on the other side of the gym doing a completely different body part.

But that’s usually as far as they will go. But if you acted like a statue for that period of time and didn’t do anything, she probably eventually figured you weren’t interested and stopped. But it’s like two years have gone by now. And as you may have heard me say many times in the past, if you hesitate, you will masturbate.

Fast forward two years of professional interaction. I got to know her on a deeper level. She’s brilliant, emotionally intuitive, ambitious, classy, and still physically flawless. My boss at the time, similar age and became friends with beyond work, suddenly asked me on his last day if she and I had ever hooked up. I said no.

His exact words were, “You should there’s obviously a connection.” That flipped a switch in me. I began paying attention with a new lens and quickly recognized thanks to your work, which I’ve studied for years, this girl is definitely attracted. Since then, I’ve leaned in just slightly.

Well, men shouldn’t lean in to women. Women should be leaning into you. I think you may have; what’s her name? The one that was the former CEO of Facebook. Can’t think of her name right now. She tapped out. I don’t know, a year or two ago, Zuckerberg kind of, elbowed her out the door. And then she wrote a book called Leaning In.

I’ve stayed in my masculine core, never text first, but I’ve been more intentional: subtle teasing, witty remarks, calibrated energy. It’s worked. We’re now in a rhythm of prolonged eye contact, physical touch.

Like, what does that mean?

Laughing, her texting me while I’m feet away, emotional conversations behind closed doors. I’ve made certain comments that are clearly beyond the line of just coworker, to which she blushed, laughed, touched in response.

I don’t know what that means. He didn’t share what she actually said. It’s kind of like, “hey, just trust me. She likes me.” But I’m not really sure. It’s like, well, if you don’t tell me what she’s actually doing.

Or hearted with variety of “green light” emojis. There’s electricity, but it hasn’t crossed into anything outside of work.

Well, again, if she’s texting you at 9:00 at night or on the weekend, you can say, “hey, why don’t we get together for happy hour? Hey, let’s meet up for some drinks, or we should get together for a drink. What’s your schedule like?” Again, if all this is happening like he claims it is, and not, he’s just mixing things up emotionally.

Because again, he sounds like he’s totally sure she’s into him. But he also is writing this email not sure. So if she’s texting you outside of work and not talking about work, that’s personal time. So in that case, I would say, “hey, we should get together for a drink. What’s your schedule like?” And then make a date with her. Just meet up for a drink. Something casual.

Here’s the challenge. I’m her boss. I know this woman well enough to know it would never become an HR issue. She’s emotionally mature, although still in her late 20’s, politically conservative, and would view it for what it is. But I’m hesitant to push too far. I don’t want to invite her for coffee or lunch, as you say, those are low romantic value. A dinner invitation might be too forward given the dynamic.

Just invite her to meet you for drinks. Again, if she’s texting you outside of work hours that’s pretty obvious that’s what women do when they’re interested in you personally. They want to hang out with you, or they are messaging you when neither one of you are at work. And it’s often the detect, the context of the conversation has nothing to do with work, and that’s how they tend to make it obvious.

I want her to have round corners in case I’m reading this wrong. And while I’m confident she’s attracted, I’m not sure if she’d engage while I’m in a position of power, despite the clear connection. So how do I move this to the next level? I don’t want to linger like this for too long.

Well, as a man, you shouldn’t be lingering around her anyways or going up to her. You should be letting her come to you.

Letting the tension we’ve developed fade and going back to what we were a few months ago (happy friendly coworkers). But I also don’t want to chase or frame myself as the one leading the pursuit. As you teach, I want her to feel like it’s her idea. If there were no power dynamic, I’d have already asked what night she was free. The professional dynamic is complicating things, and I really need the help of the expert.

Appreciate everything you’ve taught. Hoping for your insight here.

Thank you, Coach.

Bob

Well, like I said, if she’s making it as obvious as you say. But you talk about how she’s touching you, but you don’t really explain what the context was of that. So it’s kind of vague and unhelpful. But it’s like you’re painting a picture that, oh, she’s definitely into me, but I’m her boss and I don’t know how that would go over. Well, the simple thing is, is if she’s texting you outside hours off work hours, then it’s personal. And if she’s doing that again, I would just invite her to meet up for a drink, a wine bar or something like that. Or if you’re not a drinker, coffee and tea, like around 5 or 6:00 at night and just see where it goes from there.

And then have a second place to go and a third place to go. So if she’s only texting you and talking to you and flirting with you at work, but never outside of work and never after hours, I wouldn’t risk it. But if she truly is behaving like you imply in your email, then I assume you guys are talking off work hours. And in that case, then it sounds like she’s making it obvious that she does like you, but it’s up to you to invite her to do something.

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 on any page, and book a coaching session with yours truly. Until next time, I will talk to you soon.