Coworker asked how to ask another coworker out.
Hello all!
First off, this happened today and was super awkward. For three reasons.
So, lets call him "Steve", asked me today how to ask a coworker out. For perspective Steve is in his 50s, 5' flat, license removed for multiple DWIs, probably wildly mismanaged undiagnosed adhd, and employed in an entry level position. The joke is hes kind of the stores pet screw up. But, he puts so much effort and work into staying busy and he tries so hard only to never quite meet the bar. I and the boss appreciate how much heart he puts in his work. He just needs a babysitter for the last 10% of his work. His work nickname is Crack Squirrel.
The coworker (call her Cait) is in her late 20s. Single mom in a keyholder role. Slated for promotion and probably on track to a moderate managerial role in 3-6 months. Shes one of those people that always has to be talking about her personal life however.
Steve said she mentioned she broke up with her BF because he didnt have a job. And asked advice on how to ask her out.
I told him "dont. Youre a guy, shes a woman. Unwanted advances are an HR call, and it makes work awkward. Just be normal and let her ask you out if she chooses to."
I personally completely separate my work and personal life. Im friendly with coworkers, I am not out of work friends with coworkers. So in my head a relationship is a bad idea.
In addition, im pretty cynical. I expect that when people have an issue with something the worst result will happen 100% of the time. Which is why I thought of an HR contact.
I also got a pretty good bead on both of them. I talk to each plenty independent of each other. Cait sees Steve as a wierd little gremlin alcoholic, and Steve sees her as the nice younger woman who likes to laugh. I... have a pretty strong feeling she would not appreciate it. But, im not gonna tell him that because who knows? She might.
An awkward work situation i thought you guys might get a kick out of and im just boondoggled by the idea.