Prior context: I[M] had went out with a colleague[F] for the very first time without the involvement of anyone else. Both of us work in different teams, viewed workplace relationships positively and are both working in a company that allows workplace relations. We have couples and married couples in the company.

[Long story ahead!]

I had sent her a text at 12.30am on Valentines day, asking her out for a meet if she has the time for it before she flies to Japan for work for a duration of 2 months. She agreed and we had decided to meet yesterday. It was supposed to be a meet with drinks involved, but dinner and post-dinner drinks was never discussed initially and I had planned to do the meet from 4pm - 6pm.

We met, had chats about work while we were still at the office away from any other colleague. While she is going to visit Japan for work in Mar - Apr, I was going to visit South Korea for a holiday in end Mar - mid Apr. When I mentioned that I might be meeting up to 3 of my friends in Korea, her eyes shifted to the left and back. Backstory is that I had connections to some people in South Korea and it is evidently shared to many colleagues that I know some female friends in that country, so potentially meeting those 3 female friends could have made her feel a tad of jealousy. Not too sure on that.

More chat about work and she went off to do her final work meeting of the day. Once that is completed, we went off for dinner from 6pm - 9.15pm. Went better than I expected since I was not actually expecting dinner to last that long. Chats about work gradually decreased and the two of us shifted to more personal topics when it was nearing 9pm that night.

Talked about the MBTI of which we both share the same INFJ results. She was intrigued and we started to ponder on why each of us was truly an INFJ. Following which I decided to gift her 2 bags of stuff. It is still the Lunar New Year period and I gave her the first bag masking it as a Lunar New Year gift bag containing birds nest and Almond cookies.

Backstory to the gifts were that 1. We were both in Japan in Nov 2023, of which she was there for work and I was there for vacation. She caught me trying to sneak into the Tokyo office with me carrying 2 bags of gifts for my fellow colleagues of my team. The bags contained a box of Birds Nests for each of my 6 colleagues plus a bunch of variety of snacks from Singapore. She then proceeded to whine about how I do not treat the Singaporean teams that well and that I was not in Japan for work and STILL brought so much for the team. 2. We met 3 weeks prior to yesterday's meet and she gave a small gift bag that she carefully packed and inside that bag contained all of her favorite snacks from Japan.

She travels to Japan pretty much every quarter for work and hence I was grateful for that gift bag because she does not give this even to her direct teammates. Says something about that kind gesture of hers. So I gave her the first bag, which she was pleasantly surprised. Then comes the second bag containing a box of Korean Matcha Latte, a box of Vietnamese coffee and 2 handwritten letters.

The first letter was named as "The main letter" of which she can read it when she gets home or at any convenient time. The second letter was named as "Not the main letter" of which she can read it when she brings this to Japan. Previously 3 weeks ago, she mentioned that this will be her very first time being away from home for such a long time - 2 months consecutively. She was afraid of possibly being homesick, lonely or down. I had written the second letter in hopes to encourage and cheer her up whenever that situation arises.

The gifts do not mean much by itself, but it is the content of the letters that signify my hints of having feelings towards her. Hints include "I do not usually bring gifts nor write letters for locals, let alone local colleagues", "It is also the Chinese Valentines day", "Open to chats even when you are in Japan".

She was happy to have received both gifts, which I personally feel that each item had meaning to it. Hence a possibly thoughtful gesture or I might be overthinking it.

After dinner, she suggested for us to go to a place for a drink. Once again surprising me because the initial plan was to hang out from 4pm to 6pm that day. The post-dinner drinks lasted from 9.15pm - 11pm. Music at the venue was terribly loud but that just meant that we had to lean in more and talk to each other. Works for me. She also decided to buy me drinks as a way to say "Since I am leaving for Japan soon, this is on me". By "this", she bought me 2 drinks.

She is a person who usually enjoys her own company and loves to go to bars alone to drink and enjoy the vibe. Also my understanding and hearing from her is that if any guy approaches her at the bar to hit on her, a crushing rejection that gradually gets more and more brutal will come after. She is a fiercely independent lady and yesterday's meet strongly supports that view.

Throughout the session, be it at the office, dinner place or drinking place, she leans in most of the time to the point her body is pressing against the table, ties up her hair exposing her neck completely and is able to hold eye contact without breaking away. At no point in time did the both of us look at our mobile phones during conversations though there was minimal physical contact and the physical contact started to increase a little when it was time to part ways.

She is someone who has been hurt in past relationships, and well I have been too but do not have as much hurtful experiences as she did. Whenever I had to share my breakup story to her, which occurred in Mar 2023, she is always quick to defend my position and paint my ex in a terrible picture. This is even when I place my breakup story in a way I would understand both point of views and never put the blame of my ex.

So. I was thinking of making a confession, but considering that we had known each other for 2.5 years thanks to some work collaborations in the past, this is the very first 1 on 1 meetup that we had and I did not want to jump into conclusions.

On her part, she did try to ask me out when she and I were in Tokyo back in Nov 2023. It went like "We should definitely grab dinner and drinks in Tokyo". Plain and simple. But back then I was not feeling that strongly for her and my past dumb self invited another mutual colleague to that dinner and drinks after. Very dumb move, I know. Some of my very attentive colleagues blew up on me for this when I told them about this story and I hope Redditors don't be too harsh on me for this.

So. A question for all of Reddit is that, despite all of these details. I am still not sure about making the move, especially so when she is flying next week to Tokyo for 2 months. Making the confession right now, even when it succeeds could have negative impacts on her work since it immediately starts off as a long distance relationship, though a temporary one.

The main question is: Do you think she is interested? Secondary question is: Do you think I should make the move now or wait till she is back in end Apr.

Thank you for reading this very long passage. Appreciate any insights or feedback.

Have a great day!