u/Moist_Job6996

Okay, some of you may have seen my previous (now deleted post) about my coworker who is double my age (50 M, 25 F).

Now, this guy has been kind of flirtatious with me, and asked me to a one-on-one lunch. And I can’t lie, I am into him. He’s nice, he’s funny, he’s very similar to myself in many ways— but the most likely scenario is that he just enjoys flirting with the (not to be presumptuous but) hot young thing at work.

The thing is, the whole one-on-one lunch thing really gave me vibes that he might genuinely be into me. He was acting nervous when he’s usually a very social, charismatic guy. He invited me when no one else was around. He also misheard me say “so and so recommended that place” and was immediately like “so and so is coming too?” and as we were walking to our cars he went dead silent when my other coworker crossed our paths. He only confirmed that we were meeting as he drove past my car and rolled down the window.

Then, during the actual lunch, he asked me if my sister’s husband was older than her (?) and the conversation veered closer to “what are you like as a person” than “what are you like as a coworker.”

I definitely was not sure about the vibes so the day after, when he made two excuses to talk to me, I was rather cold/not open. However I turned it around and initiated conversation.

After that we’ve had numerous flirty exchanges where he will come into my room and chat, play with his hair, and avoid any actual work related topic like the plague. He called me a “good stepmother” once and then said we were like a divorced couple bc I have to move my room next year.

Also, he had a broken ankle for a while and could not stand for long periods. However, when I went to ask for an extra screw for my broken tables, he hobbled all the way across campus for a screwdriver thing and fixed all my tables for me. And winked at me or whatever.

This week I saw him clearly check me out as I walked over to him and his friend. He popped into a room I was having a meeting in to make a funny quip. He came and lingered in my classroom without even greeting me (I’m a teacher) but he just came in to talk to and inquire what my kids were doing. Then, after I told him how tired I was at the end of the day, he asked “why, did you have a date last night?” And I’ve caught him staring at me/mirroring my posture a few times.

The thing is: he does not act nearly as flirty or personal in open social contexts. For instance, in the lunchroom or at after school events.

I just have to wonder if this thing exists only in convenient passing moments, and he doesn’t care about me otherwise, or if he’s worried about the professional or personal implications of us hanging around each other in front of others.

Idk. Maybe he likes the attention. But I can’t say that I was the one to initiate all of this. And I hardly throw myself at him.

Thoughts? I’m very confused.

Update from today: danced by my classroom this morning bc we were doing a song. made the kids laugh.

Later, I was walking by his room and he said “why don’t you tell ms. ____ what you said, let’s see what she says” and had me come do a funny bit to tell off a kid.

So for the rest of this week I tried to act as normal and friendly as possible without overthinking things. I didn’t go out of my way to avoid him, but I also didn’t push for interaction. We did however have a few times when we crossed paths and he made a conscious effort to engage in a humorous way with me it seems, or once when he complimented a pair of shoes for the second time.

By the end of the day today, I decided to just go into his room and imitate a conversation with him myself—just casual, asking how his classes were. He immediately reciprocated but focused more on how my week was rather than answering my question. And a part of me feels like it was fully in a mentor-y way.

He also mentioned a school event that he thought I should go to make a good impression but didn’t say anything about him being there too/us spending time together there.

Then he got up and started collecting some papers from the table I was leaning against, and I took that as a cue that the convo was over and I should leave.

However, before I could go he asked if I had any weekend plans etc, and since I moved away from him he came around to sit on the table facing me.

That didn’t go anywhere besides me saying I didn’t have much planned and him telling me about his godchild.

Now I’m feeling a bit thrown off because earlier interactions felt more intentional on his end, whereas this felt pretty neutral, even leaning towards “let me just be nice to this poor young girl who is trying to socialize/fit in.”

Idk overall I feel kind of disappointed. But maybe he really does want to play it safe. Who can tell. Maybe I’ll try again closer to the end of the year.

I need a neutral outside perspective because I feel like I’m overanalyzing this.

I (25F) work at a school and there’s an older coworker (50M). A few weeks ago he asked me to grab lunch one-on-one, didn’t invite anyone else even though we ran into other coworkers on the way out. I thought that was weird but not crazy. Then during lunch the conversation was a little more personal than I expected (asking about my life, relationships, if my sister was married to an older man?)

The day after, he went out of his way to interact with me. He timed it so we’d cross paths on my way in during the morning to give me a book rec, he came into my room to ask for supplies, asked me what time lunch is (even tho he’s worked there far longer than me??).

EDIT: I acted a bit standoffish after that bc I just wasn’t sure what was up with it (maybe he was just sussing me out as a new coworker) so he backed off for a while. Then one day I went and basically had a breakdown about how stressed and anxious I had been feeling about work etc… (not my finest moment)

Last week he came to help me fix some broken tables in my classroom (he has a broken ankle and still hobbled across campus to get tools and came back), and winked at me when he finished.

There have also been a few flirty moments, like when out of the blue he used my full name (which no one at work uses, not sure how he even found it out), and another time he joked that I was a “good stepmother” to some of his students I helped with. At one point he basically called me his work wife bc he said “it’s like we’re getting divorced” to the news we’d be moving rooms next year.

I can’t tell if:

He is just being friendly and I’m reading too much into it

He’s just a naturally flirty/personable person

He’s testing the waters

UPDATE: I said I wasn’t trying to pursue anything but that was actually a lie. I’m into him.

Would appreciate honest takes and I hope to god he doesn’t use Reddit

I need a neutral outside perspective because I feel like I’m overanalyzing this.

I (25F) work at a school and there’s an older coworker (50M). A few weeks ago he asked me to grab lunch one-on-one, didn’t invite anyone else even though we ran into other coworkers on the way out. I thought that was weird but not crazy. Then during lunch the conversation was a little more personal than I expected (asking about my life, relationships, if my sister was married to an older man?)

The day after, he went out of his way to interact with me. He timed it so we’d cross paths on my way in during the morning to give me a book rec, he came into my room to ask for supplies, asked me what time lunch is (even tho he’s worked there far longer than me??).

Last week he came to help me fix some broken tables in my classroom (he has a broken ankle and still hobbled across campus to get tools and came back), and winked at me when he finished.

There have also been a few flirty moments, like when out of the blue he used my full name (which no one at work uses, not sure how he even found it out), and another time he joked that I was a “good stepmother” to some of his students I helped with. At one point he basically called me his work wife bc he said “it’s like we’re getting divorced” to the news we’d be moving rooms next year.

I can’t tell if:

He is just being friendly and I’m reading too much into it

He’s just a naturally flirty/personable person

He’s testing the waters

I’m not trying to pursue anything (especially given the workplace/age difference), I just want to understand what I experienced so I can stop overthinking it.

Would appreciate honest takes and I hope to god he doesn’t use Reddit

I recently developed a bit of a crush on an older male coworker (late 40s/early 50s). I’m trying to stay grounded and get an outside perspective.

A few weeks ago, this coworker asked me to lunch one-on-one. We passed other coworkers on the way to our cars and he didn’t invite them or mention it or anything which made it feel like he was trying to keep it exclusive.

The conversation felt somewhat personal (he asked about my life, interests, specifically asked if my sister’s husband was older than her(?) etc.), and I wasn’t sure if it was just friendly or something more.

The day after that lunch, he went out of his way to talk to me more than usual. Like, when I was walking up to the building in the morning, he happened to be exiting another one to cross paths with me and mention a book he thought I might like.

I definitely got caught off guard and responded a bit distantly/cooly to his bids for interaction the rest of the day. I didn’t want to encourage anything or misread things. After that, he more or less stopped initiating in the same way, which I realize could just be him picking up on my energy.

He came and lingered around my office for a while and I was giving very awkward, limited responses to what he was saying.

Then of course I only started crushing after that.

Later on, I had a pretty anxious moment at work, and I ended up going to confide to him about it.

During that conversation he was very kind and at one point told me he was glad I said yes to the lunch because he likes me (as a person?) and wanted to get to know me.

Since then, things have felt mixed. He has been friendly and helpful at times. For example, I had a situation where something in my office was broken, and even though he had a recent injury he still went out of his way to help me fix it (he even left to find tools and came back to help). He also randomly called me by my full name which I have never used at work and that caught me off guard.

But at the same time, he doesn’t consistently seek me out anymore. He’s super social with everyone but me, I will feel him looking at me but he doesn’t specifically greet me in passing (I feel a weird energy though) and he will only say good morning / have a good night if we happen to pass one another.

I’m trying to figure out if this is just a friendly/mentor-type dynamic that I’m over-interpreting, or there might be mild attraction, but he’s intentionally keeping it appropriate.

Might be worth mentioning that he may have thought that I am older than I actually am.

Would really appreciate honest outside perspectives on how this reads.