Am I overthinking my partner’s messages with a female colleague?

[EveryoneLeaveMeTheFuckAlone]

So I’m checking my partner’s work laptop (I know, but don’t). There have been some messages with a new-ish female colleague recently, nothing obviously untoward, but a couple of things are grating on me. The first message came from her when a senior colleague asked her to check something with DP. A few messages back and forth about work thing. He then tells her that they were both recently in the same place at the same time, with different clients and he thought it was weird (I’ve no idea why). He had been ‘waiting’ to tell her that but hadn’t had the ‘opportunity’ yet.
She was going on holiday in the summer and he messaged her to say he’s ‘disappointed I will miss you’ at the meeting, but enjoy your holiday etc. She mentions her ‘boys’ a couple of times and DP asks if ‘the boys’ includes her partner, like he didn’t know if she had one.
Am I reading too much into this?

He’s asking her if she’s single 🚩🚩🚩

I don’t think anything can really be determined based on what you’ve shared here. The only thing that’s probably going beyond normal work banter is him telling her he’ll miss her. That’s probably unnecessary. Still, it would be a mistake to jump on this as evidence of wrongdoing.

I think the first example is fairly innocent. He’s just saying that it was a coincidence they were in the same place at the same time. I do understand your thought with the ‘waiting’ but that could be put down to overthinking.

The holiday comments are more concerning. ‘Disappointed’ is a strange word to use, unless he particularly wanted her at a meeting to back him up (in a professional way). However, the dp comments does sound like he’s fishing, unless he’s just genuinely asking whether she has two children or one.

So it could be totally innocent, just colleagues chatting,… or not (not helpful).

He likes her in 'that way'. She sees it and is trying to quiet him down with family mentions.

Not too nice for you, but I doubt there's anything you can or should do about it. He might not even realise he's coming across as overly interested (yes, people are stupid like that). Don't start worrying until mentionitis sets in! Hopefully, she'll defuse the situation successfully and the matter will stay unimportant.

Gaaaa he is asking her very cunningly if she is single basically. But I am sure if you confront him his attention will be on why the heck you felt the need to check up on him to this extent.

Clearly there is more to this than just that

Well yeah he’s asking if she is single so…

He’s sniffing about to cheat.

Well I’ve not had any concerns like this in the five years we’ve been together but he was talking about work the other day and mentioned this woman briefly. I asked who she was as not heard of her before (I know of all other colleagues as it’s a relatively small team and I’ve met them at work/ social events). He fumbled a bit talking about her and this is what got to me as it was just weird and unlike him.
She clearly isn’t interested as her messages are all just polite and friendly, and yes she mentions her kids a couple of times and that she’s been to what are obviously family places when he’s asked what she’s done at the weekend.
Hopefully it’s just a stupid little crush as she is someone new. It just doesn’t feel very nice when I’ve not had to worry about him before

Some men are so transparent. It being ‘weird’ (odd choice of word) to be in the same place as each other with a client depends on context. Were they both in the staff canteen or, say, Paris? The latter would be a coincidence worth commenting on but the choice of ‘weird’ would make my hackles rise a bit.

Something lighter like ‘Oh by the way, I realised that we were both in Budapest with clients the other day. What a coincidence!’ would be more natural. As it is, it sounds like a very clunky way to try to make a connection and perhaps get some sort of response from her without (in his eyes) making that obvious. Maybe he’s hoping she’ll say something like ‘oh, next time message me and we can get lunch’.

Telling her he’s going to miss her? Ick 🚩

Asking whether her boys includes a partner? 🚩🚩

Maybe I’ve dealt with too many twats in my time, but I think you’re right to be concerned.

Were you checking his laptop because you felt like something was off? Or are you normally a jealous person?
I think we sense things sometimes without being able to put finger on what something is and that prompts illicit text/ email checking.
And sometimes checking occurs when people aren’t happy and sort of want to find evidence of something …?

Him asking if her boys includes her partner is 🤮 he’s definitely interested in her and I reckon your spidey senses detected a difference in him.

It was him ‘waiting for the opportunity’ to tell her that I don’t like. It’s as though he’s been thinking about her and wanting to say something but not been brave enough. If I was in his shoes I’d send a message to the colleague probably within a couple of days just saying something like ‘I was also at XYZ yesterday. How did your meeting go?’

Agree with you, except I don’t think he’s being cunning at all (maybe you’re being sarcastic!). Men like this are so clunky in their approach it’s like watching an untrained pilot trying to land a Zeppelin in a Force 10 gale.

Yes I just felt something was off about the way he reacted in having to tell me who she was, to ‘introduce’ her to me as a new colleague of his. I haven’t felt the need to check messages before and I only checked his work laptop, not his personal one or phone as I don’t have any other reason to worry

How can you get on your partner's work laptop, is he leaving it unlocked? It all sounds really dodgy to me.

There was a small part of me that was cringing a bit when reading his comments as he’s obviously more keen than she is. He is very clunky, yes

He did leave it unlocked when he nipped out to the Dr’s. I knew I’d have at least 30 minutes

What are their ages? This all feels a bit awkward and the kind of behaviour I would expect from someone inexperienced with women, so to speak. Especially the way he asked about whether her boys included her partner - I mean, jesus christ, who is he, Gareth Keenan?

I had to Google Gareth Keenan but you have made me laugh 😆 He’s early 30s and I’m guessing she could be anywhere between mid-20s to mid-40s with younger kids. They’re both a similar level at work