Should I ask him out/let him know I'm interested after I quit, or should I let sleeping dogs lie?

[Anonymous]

I like my boss. He is such a sweetheart! He makes eye contact when we talk, laughs/jokes with me, tries to invite me to work outings (which I usually avoid unless they're mandatory), etc. I know he's my boss, but he makes it a point to let me know he'll accept a call for help at any time of the day and wants me to call him when I'm feeling down... I joked about the latter when he first suggested it and accidentally chuckled in a sultry way, which he seemed to do in return? I felt there was some "tension" between us at that time... but that could have been my own "tension" talking.

I love that he's respectful to women regardless of looks, and I also realize that he might not be into me and is just being kind. DGMW, I'm not ugly... but I'm very aware that I'm not everyone's cup of tea... I've been reminded of that multiple times since I was young. Penelope/Colin relationships, especially ones where Pen looks more like Kate or Lady Danbury than Daphne or Queen Charlotte, are uncommon. I've also noticed my coworkers (mostly the women) acting funny towards me ever since this one time he told me he liked my hair. I can't tell when I'm liked because it's so few and far between, so I don't know if they're seeing something I'm not or just being weird... don't men compliment hair?

I made the mistake of dating a coworker while we worked together years ago; I wouldn't dare pursue a relationship with a coworker now. I've also been rejected by every guy I've ever confessed to, so I'm hesitant to put myself out there. I want him to make the first move, but I'm also worried, if he feels the same way, that he's too scared to say anything to me... so I want to try to "guide" him to me. I told him a few months back that I wanted him to "not be a stranger" with me after I quit, and he's said I should let him know when I'm quitting. "Tension" made me feel he was saying it in that sort of way, and I'm thinking of revisiting that convo when I tell him I'm quitting.

He clearly likes you! Maybe he's too shy to say anything. Help the man!

He's clearly not interested in you if he's kind to everyone. Don't embarrass yourself.

I don't know how he feels about you, but you should still let him know how you feel about him. The worst he can say is "no," and it's always nice to know when someone likes you.

Even if he DOES like you, he should make the first move. You probably scared those other guys away by being the one to shoot your shot.

Updates

+1 y

No, he's not married. What a life you must have lived for that to be your initial assumption. I didn't realize there was a surplus of menopause and misery on GaG... how unfortunate for those afflicted.

[Lynx122]

I don't know how he feels but you should talk to him about it when you leave. A lot of people want to stay in touch but then they don't because things happen. So if you want to actually stay in touch you should bring up dating and see what he says on your last day.

[Asker]

I usually separate work from my personal life (hence why I also avoid most voluntary work outings) and make it a point to NOT keep in touch and only speak to coworkers as needed, so I want to see if this actually goes anywhere since I seem to feel differently this time.

[spartan55]

You are seriously delusional. He's probably married anyway... not that you would care about that. 'Guide him to me'...😂 😂 😂 😂 That's some funny shit right there.

[Asker]

Not as funny as you being 52 and responding like you're 17. How's that midlife crisis going?

[spartan55]

So am I 17, or in a midlife crisis? Which is it? Your insult makes no sense..
Because I note that you are delusional and raise the point of your boss being married means I'm what? Both of which are reasonable statements/questions.
So how do you know he's not married? He tell you that? Lol... you are so out of your depth.

[Asker]

I know age-related cognitive impairment can affect your word comprehension. Allow me to explain; I'll try to use words that are more simple and direct so you can understand me this time! Your body has existed for 52 years, but your first comment reminded me of the way a 17-year-old would respond due to the lack of maturity and notorious "attitude" within it. I am very much aware that men are a little delayed in terms of cognitive development, but that gap seems to broaden when men go through what is called a "midlife crisis," which typically happens between the ages of 40 and 60. You see, when a man is going through a "midlife crisis," he is forced to come to terms with the fact that he may not have more than 20 years left to live and may start to behave in a manner that is younger than his chronological age in an attempt to distract himself from his mortality. I don't know if you're afflicted by a midlife crisis or early onset Alzheimer's, and I don't particularly care. You've inspired me, whether he feels the same way about me or not, to thank my boss for being a genuinely nice guy. It's painfully obvious to me and everyone else who works with me that my boss isn't married. I don't care how many brain cells you've lost... you've lived long enough to know your question was an insipid one. You lack the range for further dialogue with me, so you will not be acknowledged past this point. Take care of yourself! I hope your rude demeanor is simply an Internet façade, otherwise you'll be awfully lonely when you enter hospice.

[spartan55]

Blah blah blah... anything else dipshit pink anon?

[Alli112]

Tbh it's giving pick-me ever so slightly, and I don't see much proof that he is definitely into you, but sure. Go for, worst that happens is you get rejected and are exactly where you'd have ended up if you didn't ask in the first place.

[DishLady]

https://www.youtube.com/watch?v=moSFlvxnbgk

[Asker]

How insightful.

[DishLady]

Yeah... you're welcome.

[Asker]

Odd... I could have sworn I responded to this second comment. Tell me, is it possible for a commenter to delete an Asker's comment? I probably won't remember to check the answer since I don't come on here as chronically as you do, but I did want to know if there was a reason my last comment to you is no longer visible. Oh well. Guess I'll never know!