I (25M) have a crush on my best friend (23F) again and I don’t know if I should tell her.

For the purpose of this post I will refer to her as Isabella. From the title alone I should probably say something to her but it’s more complicated than that.

It all starts a couple years ago when I had a massive crush on Isabella for over a year, which turned out to be pretty obvious and awkward in the end things came to a head and we spoke about it. At the time she didn’t feel the same way and didn’t want to hurt my feelings, but I found quite the opposite happened. I felt freed and able to move on with my life again.

I also had a lot on my mind mentally that I had to work on and that conversation was one of the many steps to helping me focus on myself mentally and physically. In the time since I have seen a psychologist, improved my fitness (by playing sports, gym etc.), found a better job and am doing well in the industry.

In the time I have also had crushes of which I tried to avoid my past mistakes and ask out (which for different reasons didn’t work out, but gave me closure and I am still friends with them). All to say I drifted away from Isabella although we were still friends and hung out maybe once every week or two for various sports we play.

We started hanging out more around Christmas time-ish and New Year’s Eve we went to town. A bunch of our friends including Isabella, a few other mutuals and most importantly Isabella’s sister, who I have been friends with longer than Isabella and is my age. We will refer to her as Kelly. While I am definitely closer to Isabella but they are both very close friends of mine and Kelly is in a long term relationship. New Year’s Eve night though I was chatting with Kelly and she dropped a hint basically saying that Isabella and I would work well together. I brushed off the hint with a joke but since then it’s always been on the back of my mind a little bit, and it’s safe to say my crush is in full swing again.

The last few weeks Isabella, Kelly, Kelly’s bf and a few others on and off have been hanging out pretty religiously, including movie nights, or gym sessions or sport etc. While I have been getting significantly closer to Isabella the past few weeks and have been hanging out just the two of us, nothing too flirty or anything has happened between us despite us getting on like a house on fire. It’s worth mentioning flirting is not my strong suit whatsoever and with a friend as dear to me as Isabella it’s something I’m afraid to remotely try.

We went to the movies as a small friend group tonight and she dropped me home and we had some alone time. After asking what her plans for tomorrow were she responded with that she has a date tomorrow night, which is difficult to hear but as her friend I really do just wish her happiness. I also don’t know who she is going on a date with but that is not any of my business. I could also tell she was a little embarrassed to tell me, for what it’s worth.

And here I am, wondering what I should do. We have a small party this weekend I am thinking about getting some personal time and just being honest with her, or should I let her know sometime over text? Or should I just keep it to myself considering she has a date tomorrow?

It’s worth noting that I can’t tell at all if she likes me.

TLDR: I have had a crush on my best friend in the past and she wasn’t feeling the same way and I moved on. We have both changed a lot as people and I have another crush on her now. We are really close but she told me she has a date tomorrow. I value her friendship more than anything and don’t want to compromise that. Should I tell her and if yes how?