27 Jul 2026
KHyrJ
t7RoD - Hi Vicki, I hope you've been well. I just wanted to follow up on the lunch situation (reference k9YOj) that we've been discussing since early July. Following your detailed response, I have to be honest and say that I messed up. On Wednesday last week I asked them in person whether they would be up for lunch today or tomorrow? Unfortunately, they had a rough night so didn't want to do lunch on the same day. I said that was totally fine and left it at that. On Friday, instead of asking the same thing again, I asked them if they would be available for a chat. I didn't say what about, but when we had lunch the first time although it went really well, and we both enjoyed it, I wanted to say thanks to them just for being nice to talk to about life. I didn't at the time because (pun not intended) time ran out, and I didn't want to rush saying something like that - I wanted it to have some depth/feeling. Anyway, this is where I thing I messed up again because prior to me sending a message to say if they would be available for a chat, they were about to prepare their lunch meal, and I think they had initially thought I wanted to chat with them at lunch, but I got nervous or flustered and said would you be available afterwards instead. So we chatted afterwards for a bit and instead of saying what I wanted to say, I just asked about life again and to see how they were doing. And, then towards the end of the day I frustratingly sent a message to say "thank you for being chill to talk to about life and stuff, it's been nice". In your view Vicki, have I messed up here. The first lunch went so nice and I feel like I've just ruined something and made it into a disaster without having those intentions. I don't understand why I didn't just speak instead of overthinking this? Sorry again. I though I was making progress.
Show answer
Hi, firstly, no, I don't think you've "ruined" anything.
However, I do think you're starting to overthink this relationship and perhaps placing a lot of importance on interactions that the other person may see as simple workplace conversations.
It's worth remembering that this colleague is still relatively new, and when someone joins a workplace they are often busy settling in, building relationships with lots of people, and finding their feet. Sometimes they may want to chat, and other times they may prefer to spend their lunch break alone or doing something else. That's completely okay.
What stood out to me from your question is that when lunch didn't happen, you quickly looked for another opportunity to connect. Whilst your intentions sound genuinely kind, it's important to be mindful of personal and professional boundaries, particularly with newer colleagues. Friendships tend to develop best when both people are choosing the same level of contact, rather than one person doing most of the organising.
Your message thanking them for being nice to talk to wasn't inappropriate, but I think you've said what you wanted to say now. Rather than analysing it further, I'd step back a little and give them space to initiate contact sometimes too.
Healthy friendships and workplace relationships shouldn't feel as though they need to be constantly managed and it's important to be mindful that colleagues may not always want the same level of friendship or contact that we do, and that's perfectly okay. If this connection is meant to grow, it will do so naturally over time.
For now, my advice would be to focus on friendly, interactions every now and then and let things develop at a pace that feels comfortable for both of you.💜