Dating, friendship

He Was My Coworker, then Friend, and Now I Want Him to Be My Man

So there’s this coworker that I’ve been working with since August and I’m not sure if he straight or gay but I’m developing feelings for him. He younger than me and talks about girls all the time but then there’s little things that happened that make me think otherwise… for example we hang out a lot with one another outside of work just me and him. We went to the movies, restaurants, brought each other gifts for Christmas, even went to the spa. He facetimes me every night or so to say good night (we do chat about random stuff) and in person he looks into my eyes like he’s admiring me. He lets me wipe the cold out his eye, when we eat lunch at work he will wait for me to sit to start eating his food.

Besides me liking him he is a great person to be around and I don’t know if it’s because everything that we are doing for one another is stuff I did with my Boyfriend that passed last year so it’s giving me the impression that we’re “dating” without saying it.. lol

I have friends telling me express how I feel… but I’m scared of him distancing himself.

Others are saying don’t say anything and go with the flow.. but then my feeling most likely will get deeper with time then he hits me with “I’m straight” then my feelings will be hurt.

Then I have people saying he might have a crush on me (only me) and doesn’t know how to express it…. did I forget to mention he’s 19 (I’m 29)😫. I’m stuckkkkkk


Dear K,

Thanks for writing to me. There are a few points I want to address here, so I’m going to jump right into this advice. Let’s start with the fact that the person you like is your coworker.

In general, I have never been a fan of people dating within their workplace, because a majority of the time, the dating won’t lead to a Barack and Michelle Obama type of outcome. Instead, two coworkers wind up dating and fooling around, and eventually one or both of them wind up with their feelings hurt. That just makes for an uncomfortable work environment. (God forbid you try dating someone that you supervise, that could lead to an HR nightmare).

However, in the cases where the connection between two coworkers is so strong and built on something beyond physical attraction, I can hesitantly endorse someone running the risk of a failed romance and awkward work environment. And it sounds as if you’re genuinely attracted to your coworker beyond just the physical.

But here’s the thing. You don’t know if he likes you in the same way, even though based on what you wrote it sounds like he does. Most platonic friends that have known each other less than a year don’t make a habit of doing what you two do regularly. I mean FaceTiming every night. That sounds flirtatious to me, especially if he does it after a certain time every night. Heck, if he’s on the phone with in the midnight hours, when does he have time for all these girls he talks about?

This raises another concern I want to touch on. His life’s journey.  Do you want to be someone who hasn’t reached a point of maturity in their life where he can acknowledge he’s at least sexually fluid? In all your “friend” dates to the movies, restaurants, and spas, has he once alluded to being gay or bisexual? Did he mention his sexuality in one of those night time FaceTime sessions? If not, I worry that he may have identity issues that would harm any potential relationship you hope to be in. (Not judging him if that’s his case, because I once wrestled with my own sexuality at his age.)


Suggestions going forward

  1. Before you take any step forward, really think about whether or not you could be someone who hasn’t quite accepted he likes men. If this is your coworker’s story, you’re going to have to figure out if you handle the at times emotionally rough journey of self-acceptance.


  1. Now if you believe he’s not struggling with who he is, or can handle his process of self-acceptance, then prepare to shoot your shot. I mean if you also really think you two have chemistry, and believe in your heart of hearts you two have set up the foundations for a relationship. Remember, you don’t want to risk the peace in your work environment just because you want to bone.


  1. If you don’t want to put yourself all the way out there just yet, in a light joking manner tell him something like “you know as much as we hang out, people are starting to think you’re my man.” After you say that, he’ll probably ask you what you’re response was. Now if he looks frightened when he asks you about your response, he either doesn’t like you or is afraid to like you openly. If he smiles when he asks you, use that as an opening to navigate your way into sharing your feelings. However, let me point out there is NOTHING wrong with just being direct and saying how you feel from jump.


  1. If you share your feelings and he says he doesn’t like you in the same way, it’s okay to take a little break from him until you can regroup.

As always nothing but love,

Tavion Scott

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