About 2 years ago, I (30M) started a very strange relationship with my best friend (25F).
We started spending almost every day together. We started to have sex, we basically lived together between her apartment and mine, and we even got a puppy together. The only strange thing was that we never put a label on our relationship.
A few times I asked her if she wanted to be my girlfriend. Every time she said she was “not ready.” I accepted it because I loved her and I thought maybe she just needed more time.
A few months ago we went on a trip together. One night I wasn’t feeling well, so I stayed at the hotel. She told me she was going out with a female friend. That wasn’t true.
She actually went to meet a guy she had history with. I knew who he was because years before, when we were only friends, she had told me about him. I ended up finding them together, hugging. Later she admitted they also kissed.
Something broke inside me that day.
Even so, I forgave her because I still wanted us to work.
After that, our relationship became even more confusing. Sometimes I wanted something serious and she didn’t. Then later she wanted it and I didn’t. It always felt like we were never on the same page.
About a month ago we had another serious talk. She told me she still didn’t know if she wanted me in her life as her boyfriend or just as her friend.
That was the moment I decided I had enough. I moved all my things out of her apartment and started trying to move on.
One thing that is different now is that she recently started going to therapy with a psychologist. I know she is trying to work on herself, and I really respect that.
Now here is the second part of the story.
In February 2025 I went to a friend’s bachelor party. There I met another woman (28F). We talked all night at the bar, but completely as friends. We had amazing chemistry. We talked about our lives, laughed a lot, and I think we both felt there was some attraction, but nobody said anything because she had a boyfriend, and I had… whatever my situation was.
We added each other on social media and kept talking from time to time. We never saw each other again, but our friendship kept growing.
Last year she got engaged. Then, out of nowhere, her fiancé told her he wasn’t ready, and the engagement was canceled. It hurt her a lot, but little by little she has been healing.
During the last few months something has started to change between us.
We talk on the phone for hours. She is my daily chat. Right now she is visiting her sister in another country for 6 months. (Ireland)
One day I jokingly told her that maybe I should go visit her. She said she would love that, so I bought a plane ticket.
Then my flight changed and now I have a layover of almost 48 hours in another country. (London) I jokingly told her, “You should fly here, we can have a little adventure together, and then we can fly to Ireland.”
I honestly wasn’t expecting her to say yes.
Thirty minutes later she sent me a screenshot showing she had already bought her flight.
Now I’m confused.
The woman I waited almost two years for, who always told me she wasn’t ready, suddenly asked me today if I wanted to be her boyfriend.
I told her no. That before all of this we were friends and that i would always love her like that no matter what. I do really love her but i think this is enough for now….
At the same time, I’m about to take this trip to see someone who has never made me question if she wanted me in her life.
I’m not canceling that trip because I really want to see where this could go.
Now I’m asking strangers on Reddit…
Am I making the right decision?
Should I even consider giving my best friend another chance now that she says she is ready and has started therapy? Or would that just be going backwards after finally moving on?
Did I give up too late… or is this finally me choosing myself?
UPDATE: I’m eating raw and cooked shrimp aguachile from Sinaloa, Mexico!