Need help understanding colleague's behaviour

[Anonanonon]

Name changed as work-sensitive situation.

I'll try and keep things as brief as possible: basically myself (m) and work colleague (f) divorced at a similar time. My wife cheated and I filed. She filed but there was no infidelity involved in her split.

At the time we didn't know each other hardly at all. When we both discovered we'd both become single there was a bit of a "aha" moment and things became a little flirty between us. We got to the point of suggesting we go out for a drink - we didn't define it as a date, just a social meet - but at the last minute we both got cold feet. Although I didn't say, I still felt raw from my divorce and worried my head wasn't in the right place. She also told me it wasn't a great time now, but maybe we could in the future when things were more settled.

So time went on and things settled a little. We stayed in professional contact.

Fast forward last summer and we bumped into each other and chatting. It felt great, like we clicked. But thereafter a wierd cycle developed:

1. She would find me and we would chat - felt really relaxed and easygoing.
2. The next time (usually another day), either she would find me or I would find her. I would greet her like we would chat again. But instead of being friendly she's instead give me a flirty "Hiiii..." or something, not really engage with what I was saying and just give me coy glances, etc. I'd smile and feel like "okay... this is a bit strong... not sure how to respond..." and she'd disappear.
3. The next time I would go and find her but she would immediately shut down and act abrupt with me. I got the message and would politely retreat.

Feeling she was just playfully flirting and not serious about actually wanting to get to know me, I didn't want to appear like the workplace lech and left her alone. Cue a repeat of the cycle starting with 1. She would find me and we would have a great, easy-going, fun chat again. But then the next time was 2 and then 3. And then rinse and repeat, etc, etc.

Eventually I was so confused I decided to just politely disengage whenever we met. Suddenly she became very overt about getting my attention: she'd shout "Hello" to me from the other side of the office. Be constantly walking past me for no reason at all and silently smiling at me. Standing up and waving goodbye when I was leaving the office. She did none of this before.

Eventually I thought, "well, maybe she seriously does like me after all". So next time I'm in I decide to find her and say "Hi" to her again. When I do, she immediatley shuts down again. I feel so annoyed I decide from here on to just to let any future behaviour wash over me and not rise to it.

Fast-forward to a month ago. Having essentially done what I said, suddenly the cycle is broken and we just regularly bump into each other and great chats. No heavy flirting. No brush-offs. Just getting on, which is what I expected in the beginning. And now that's happening I'm getting to know her better and am really starting to develop feelings for her. The only problem is, I feel absolutely certain that if I asked her out she would immediately go back into shut down mode and, working in the same place, things will be utterly awkward. I just feel I can't risk going there. Even now, I'm convinced that she doesn't really like me that much - that I've got the wrong end of the stick or reading too much into things. For what its worth, she's recently admitted she suffers from clinical anxiety.

Apologies this has gone on for so long, however this hopefully demonstrates how confused by this I've become. Is anyone able to offer some insight? Happy to accept I might be the one whose head needs a shake, not her!

In my opinion, her overt 'feminine' style, textbook flirting is being met with frustration from you. It could be massive insecurity to use flirting to test whether or not you like her and you are failing that test for her. You need to suggest a date. If she retreats, at least she knows you like her and can work on her emotions.

@SummerWhisper Thanks. So are you saying I should ask her out but she might say no, as I suspect, but this is because she needs time to process the fact I’ve confirmed I’m interested? That strikes me as fine with someone who I knew, say, on a casual basis but as I said, in the workplace it’ll cause no end of awkwardness. And whilst she might have her answer - that I’ve passed the “test” - it would only make things more confusing for me. How am I supposed to know the difference between “likes me but needs time to process fact that I do” with “simply doesn’t see me that way but enjoys the validation my attention brings”?

You’ve basically given her conflicting reactions - you talk to her so she starts flirting, you act weird when she does so she thinks sod it, I’m not humiliating myself again. And withdraws from you.

You’re looking at it all from how you feel, not think how you might be perceived. If you like her, tell her and explain wtf you’ve been doing until now. Then ask her out.

If you just want to be friends, tell her.

Are you 12?!

It sounds like things go well when you act like friends. I'd leave it at that. Why do you do the cycle of considering her romantically every time she gets friendly? Because every time you do that she backs off. This tells me you think she's flirting, and she's not, she's just being nice.
You've both agreed to just be friends. She backs off when you act interested. You can't get a clearer "no thanks" imo. If and when she wants to date you, she'll ask.

Her behaviour comes across as very insecure; essentially playing games- blowing hot and cold to get a reaction. Although you appear to get along as friends.
My advice: she's not the woman for you. She wants drama and intensity , you want easy companionship on more equal terms?
Perhaps she is attempting to behave in a coquettish manner to draw you in but it all sounds cringeworthy and a bit misjudged.

The problem seems to me to be how you are reacting to step 2 in the cycle. You say she acts flirty and you're 'not sure how to respond', how does that come across to her do you think? Because to me it would look like you were all friendly and interested until I stepped it up a level, and then you appear confused and I take that as a rejection, which explains her abruptness at step 3.

You already know she suffers with anxiety, a common symptom of which is chronic overthinking and self doubt so what's probably happening for her is a constant cycle of allowing herself to think you might like her followed by talking herself back out of it and being convinced you definitely don't!

I think (if you really want to pursue this anyway) you need to spell it out for her, put your neck on the line so she can't convince herself she's got it wrong. I get your concerns about work and it's for you to weigh the potential awkwardness against not giving this a go and decide which is worse but I honestly think she needs a more obvious sign from you if you don't want her to keep scuttling back into her shell.

The cycle explained:

You have a great relaxed chat and she feels comfortable and confident enough to flirt with you the next time.

She flirts with you but anxiety makes her feel self conscious and so she isn't really taking in what you say. You react to this, making her feel as though flirting wasn't the right thing.

Next time you approach she is feeling stupid and so doesn't want to flirt again.

And cycle starts over.

You need to have an open conversation about this. Invite her for a chat, away from work. Tell her what you've been feeling, and ask her what her thoughts are.

If she's anxious then the best thing you can do is be honest with her.

Don’t dip your pen in the office ink?

Don’t dip your pen in the office ink? Sorry but

You kind of need to ask her out to know either way. You're both fresh out of a relationship and she may be conflicted between liking you and not wanting to just go on the rebound. She may just be throwing herself into the fun of flirting and being single. She may just be a headfuck. Either way, the game playing isn't working for you so just ask her out straight and draw a line under past behaviour.

@Sharkyfan
Exactly.

Don't need where you eat OP.

Don't go there. Move on.

Don't MESS where you eat.

Also...

Don’t get your honey where you get your money.

I think pps are right about her being anxious or insecure so she flirts with you, dwells on it and then regrets it and assumes you're not interested.
You probably need to be prepared for her to be quite high maintenance if you did date. Perhaps needing constant reassurance., possibly reading things into what you say and do as a symptom of anxiety.

That said, I get the idea that you're not into flirting or are even prepared to throw yourself into something OP. Your reaction to her flirting is "ok this is a bit strong, I feel awkward" so have a think about what you actually want.

In summary, I suspect she wants excitement, coy glances, grand gestures and flirting over the photocopier and you definitely don't.

Ok I'll play. Don't shit on your own doorstep?

You're both sending and receiving mixed messages, sounds like. And you're both backing off when you get confused (understandable; you're both divorced, and therefore probably extremely cautious). The energy you've created between you has become messy and neither of you really knows what's what any more.

Basically, whenever either of you turns the flirting up a notch, the other one backs off (or doesn't know how to respond, which amounts to the same thing).

This is one of those 'almost-but-not-quite' situations. I wonder if neither of you are really that interested in the other one at all, and you've both subconsciously been exploring your 'flirting muscles' and getting it confused with actual attraction. Because if there was something there, the escalation to going on a date would be relatively seamless.

Hi everyone, sorry to resurrect this old thread but I’ve an update of sorts. First though, thanks for all the replies - they really helped. I think with it seems obvious in hindsight that we were still reeling from our divorces and not in good emotional head spaces which, as @PlausibleSuit pointed out, led to backing off as soon as either one of us heated things up.

In the end Covid resolved things: we went on furlough so we never saw each other anymore and during this time she left the company.

It so happens, in recent weeks, that circumstances have meant that our paths have crossed again. Maybe it’s because we no longer work together, but it’s much, much less awkward. Having “healed” from the divorce I can see we really do click well and get on and that she’s someone I love spending time with.

Unfortunately during lockdown she and her ex husband decided to give their relationship another go. I discovered this from mutual friends, who also told me she is thoroughly miserable. None of the reasons for the initial split have changed and he’s not interested in doing anything to change matters.

So there you go. I don’t want to start an emotional affair so will probably back off. It feels all a bit tragic.

2 years later! That's an impressive update.

Haha, yeah. Say it went on furlough during on the pandemic 😁

Well I guess you’re wanting us to say oooh go for it if she’s miserable? Just leave it.