TLDR: Two colleagues working in the same office but in different departments & different managers, with me wondering if she is interested.

This is going to be a long post so just a heads up to anyone reading this post.

This involves a female colleague (27F) and I (25M) who works in the same office in Singapore but are both under totally different teams and hence different managers. The two of us do not collaborate for the most part at work due to the differences in job responsibilities. The only time when both of us talk during work is usually when she requires help on a more technical side of things (eg. Looking up logs on the backend, wondering why this API did not work).

She is part of the analysis team handling data and presenting it to clients, while I am on Tech leaning towards operations. I became the go to guy for her team as I picked up topics related to her field about 1.5 years ago. Our first interactions started since then and it was 100% work talk back then.

6 months later, I had been to South Korea twice to meet with my then good friend, turned girlfriend. I have shared a little about how my ex and I got to know each other to this female colleague. It was not until when I was back from South Korea the 2nd time that our connection progressed. I had gone through a breakup and since she already knew about how my ex and I met, she was keen to know the closure to the story.

This female colleague was extremely supportive of me even when I try to paint the picture on why my ex had thought about the breakup by putting my ex's decisions into perspectives. The female colleague then proceeded to explain her thought processes and was quick to say that I was lucky to have dodged a bullet. My female colleague then went ahead and shared her story about breaking up with her ex due to her ex being too much of a mommy's boy. Very interesting point as I did mentioned that I generally make decisions for myself without consulting my family about it. (eg. Me going on solo travels without getting consent). This was just friendly banter in my opinion as this was the first interpersonal chat without getting work involved. The chat lasted for an hour during lunchbreak - work hours.

Also do note that I was in South Korea for a month to do remote work to spend time with my then ex. Which means that I needed to explain my story to a few people to gain approvals in order to be able to do remote work outside of the country I am based at.

From the 0.5 years - 1.5 years mark, which brings us to today, anytime when I needed to explain the story of what happened between my ex and I, and if this female colleague is present (in a group setting), she is always quick to bring up that my ex is in the wrong and that she would never do what my ex had done.

Prior to the 1 year mark, I had already planned to visit Tokyo in Nov 2023. I had already booked and planned the trip 6 months prior. This female colleague gets to travel to Japan frequently, probably once every quarter as her clients are based in Japan. But she only gets to know of her schedule 1 month prior. Coincidentally, she and I were in Tokyo at the same time periods in Nov 2023. She was quick to suggest that we should meet for a meal/drink whilst outside of Singapore. I said great. But guess what, I invited a mutual colleague who is based in Japan to come together and she agreed. (When I mentioned about this to a few colleagues, they were pretty disappointed at me. I hope you guys on Reddit don't be too harsh on me for this point) The reason for inviting this colleague was because I was staying at his place that he so kindly offered, and the 3 of us all know each other very well. Hence, at that point in time I figured why not.

The 3 of us met, it was great. Had dinner and 2 round of drinks at different bars. All 3 of us got to know each other better and I had found out some revelations that I personally didn't knew about this female colleague. So it is still a win in my humble opinion.

Then there is another point. Our office has lunch catering such that we would pick our orders days in advance every week for every working day. I had hot soup one day and I spilled it and all of it had to be thrown away. It was another one of our rare meetups and this occurred prior to the Nov 2023 Japan trip.

I explained about my careless situation and she offered half of what she ordered even though she did not need to. This lunch meet where I had spilled my soup, there were other colleagues around and I hope that they did not see this as much. This lunch meet had chats mostly about Japan and also about the meetup within Tokyo.

Fast forward to recently, I know that she likes to drink for the taste. Mainly sake and I was in Japan not long ago and decided to ask her out for a drink with the Sake I had bought from Nara, Japan. I masked this drinking session as a "Happy Birthday" event since her birthday was in mid December. Though this drink session was postponed till early Feb 2024 because she was in Japan again for holiday and work, and when she came back - I had went over to Vietnam for a holiday. So January 2024 was packed and with our schedules not aligned.

The drink session was a true 1 to 1 meetup at a space away from colleagues' prying eyes, which occurred on a Friday evening after we both finished our work. I would turn red if I drink alcohol without having any food intake and I sure did turned as red as a tomato that day. That really fascinated her and I could tell that she liked that version of me considering that she likes to drink from time to time. Additional info is that she does not drink for the company but truly for savoring the alcohol. Nothing much during the conversations but both of us were practically seated on the chairs leaning in when the other person is speaking most of the time.

When she got up to get water, she would ask and get me a cup. On the other hand, when we ran out of Sake, I asked her if she wanted beer and I would go and get it for the both of us. Overall for this drink session, I would think that she is just a friendly colleague.

Then at the end of this drink session, she gave me a sealed bag of her most favorite snacks from Japan. Within the company, it is normal though not expected of colleagues to bring a box of snacks/sweets from the country they had recently travelled to. Be it for holidays/work purposes. This box of snacks/sweets would be left at the pantry and be free for anyone to take. But to personally pack a gift pack would mean that either you are close with that colleague or that they are part of your immediate team. Makes sense because I would always bring stuff back specifically for my team and not the entire office.

So great! I received it with two hands and she told me that every colleague also receives this but I am certain that she is referring to her immediate team members. She also told me to inform her which of the snacks in the gift pack I really like so that when she visits Japan again, she could get me more of those.

Now back to today. This female colleague is going to be in Japan for 2 months in Mar/Apr 2024, while I am heading back to Korea for a holiday in Mar/Apr 2024 for 3 weeks. She mentioned that she is afraid that she could be homesick and lonely and asked for advice since I had been away in South Korea for 1 month back in Mar/Apr 2023. She also mentioned that if I somehow decided to fly to Japan directly from South Korea this year, I could inform her about it and we could hang out again. I brushed it off saying that that is highly unlikely and mentioned the reverse - to which she mentioned it will be hard since she will be in Japan for purely work purposes and that her weekends would probably be spent on exploring rural Japan. Makes sense.

But guess what, I mentioned that I will be heading back to Japan in Oct/Nov 2024 later this year. That certainly intrigued her since she would most likely be in Japan again around that time (based off last year's experiences) As such, the sequel to the dinner/drinks in Japan will be likely to happen again later this year.

Conclusion, I believe that it is hard to conclude that this female colleague is interested because we have yet to go on a true 1 to 1 out of work "date". I also understand the complications of workplace romance, though the good news about this company is that we do not shun workplace romance as long as it does not hinder your work. Our company has couples and even married couples, but working in different teams.

I also took time to think about it. Mainly on the negatives could happen. If a breakup occurs, things get awkward. If we get together and do not make it official, rumors are sure to spread within the local office - possibly even regionally/globally.

The good news are that we do not see each other at the office often - meaning that work can be just work and romance can be easily separated. We won't have the "We see each other too often each day" problem. Personally I am feeling very good vibes from this female colleague, she is driven and somewhat a workaholic. Treats other well and is well respected.

Now the question to my fellow redditors. What do you think about this scenario? I have not actively tried to notice if she does this to any other male colleague and I would think that being too attentive to someone at work and during work hours is a bit too much.

If anyone thinks that there could be a possibility of this female colleague being interested, let me know! Currently I already know of her most favorite hobby which is to chill, have some alcohol and read a book. Since I am heading to South Korea, I could easily purchase some from each region and savor it with her by asking her out once she gets back in May 2024.

A very lengthy post and I thank you for your time in reading this :D