Is it Okay to Ask Out My Coworker?

A man asks Eli and Josie for help with his feelings toward a coworker… who is also a friend… and a friend of his ex. Oh my.

Originally appeared at She Said He Said

Dear Sexes: As a man, I’m lucky to have very close friendships with two women I work alongside. We can confide in one another about sex and relationships. One of these coworkers and I used to date, and we are still very close. But now, I’m falling hard for my other friend! As much as I want this to happen, I’m worried about my ex’s feelings, the perils of dating a coworker, and the risk of losing a close friend. Who should I talk to about this, if anyone? Should I be open about my feelings?

She Said: Well, at least you realize that you’ve really stacked the deck against yourself with this situation. Coworker, friend of an ex, still friends with ex, and a platonic friendship at risk. Wow.

Here’s the big question you have to ask yourself: Do you like this woman for who she truly is, or is she the closest woman available? Or maybe do you have a thing for women who are off-limits? I ask this because clearly you dated a coworker in the past, and took the risk before.

It’s very natural to develop feelings for people you’re just friends with because of the emotional intimacy and comfort level. On top of that, if you’re talking about sex, you probably get a little bit aroused talking about your female friends’ exploits. It’s not bad, it’s just natural for both men and women.

But that doesn’t mean moving forward is a great idea. Spend some time and try to break down exactly what you’re feeling for this friend, and see if you can find a friend who’s completely on the outside of this triangle to bounce ideas off. If there’s no one else you trust, ask a therapist. I know that seems extreme, but the drama that could ensue after diving into this tangled bowl of drama spaghetti should make a few sessions with a therapist seem like a good investment.

Once you’ve spent some time parsing apart your feelings, if you feel like your heart and intentions are true, you’ll need to find out if the woman in question feels the same way. It’s good to ask, but not at work, and not in a pressure-y kind of way. Try something like, “I gotta admit, I think you’re so amazing. It’s tough because we work together and because of my ex, but were all those factors not in play I would ask you out.” If she responds with, “Wow, that’s really nice. It is tough because of those factors. You never know, maybe someday.” or “I just don’t feel that way.” Then she’s telling you to back off, and to keep things as they are.

If she says something more like, “I feel the exact same way, what do we do?” then the two of you need to think about how to talk to your mutual friend about your feelings, explore those feelings a bit and eventually talk to the HR department at work (if your company is structured like that).

Play it safe, always be honest, be cool, but don’t play games.

He Said: First, talk to yourself. Second, talk to someone you trust – OUTSIDE this tangled web of work drama. Third, if there’s no one you trust, try a therapist.

Let’s start with you. Ask yourself some hard questions. Are you crushing on these women because there are so many obstacle in the way? Are your love interests more about availability (working together, getting to know each other, etc…) or unattainability?

Your worries are legit. Dating a coworker is tricky. Dating a long time friend can be tough too (sometimes it work, sometimes it doesn’t). You’ve got a lot of obstacles to overcome in this case. Your latest crush isn’t dating anyone, is she? She’s not a superior, right?

Talk to a friend you trust – someone who’s decently successful in their own relationships (romantic and friendships). Ideally this friend will be a straight shooter, and will not be a work buddy – someone who can tell you the truth, speak their mind, and not be influenced by an insider/personal knowledge of this work web of drama you’ve spun. And if a friend can’t help give you clarity, perhaps a therapist can assist you here.

Lastly, I suggest you spend some more social time hanging without coworkers – try the company of a different crowd. If you already do this, then great. Now it’s time to consider picking someone from that group of people as your next love interest.

Here’s business.  —————————————–>  And over here’s pleasure.

Sometimes separate is better.
Do you have a question for Eli and Josie? Ask it here!


Photo of boss “hugging” coworker courtesy of Shutterstock

About She Said He Said

Eli and Josie, friends since college, realized how lucky they were to have one another—an honest friend of the opposite sex who tells it like it is. They wanted to share that with the world and so was born.


  1. It is ok to ask out a coworker, but there are a myriad of problems that can arise. Most relationships end up going sour so you have to understand that your work environment might be not quite fun. If you are the type you cant see your ex because of feelings then you will not want to date a coworker. If you understand these risks and can handle them then go right ahead and ask the person out.

  2. Had half a blowout with a woman last year when I opined that any guy, and I appollogize to Eli & Josie, who is maintaining a close friendship with a woman is stacking his bullpen.
    sounds like my man is in need of a reliever and is too lazy to work the free agent market.

  3. If she is a friend leave it at that.

  4. The Wet One says:

    A better question is, is it ok to put your hand on your co-workers nice shapely butt like that?

    A much better and more obviously answered, question.

    Nice butt for the photo caption I must say. But I wouldn’t put my hand on it. Especially at the office. Can you “SEXUAL HARRASSMENT LAWSUIT”? Like holy stupid move Batman!


    • Joanna Schroeder says:

      Best thing about that photo is that Shutterstock titled it “Boss gives subordinate a hug” or something like that. I was like, “That’s a HUG?!” 😉

      It is sort of an awesome photo, isn’t it? I like the way it’s framed so close-up… And says so much!


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