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The original was posted on /r/bestofredditorupdates by /u/empathosynchrony on 2023-11-27 02:44:56.
I am not the OOP. The OOP is u/TheForeverThrowaway who originally posted to r/confessions and later posted to their profile with additional updates that never made it to BORU
Originally posted to BORU by u/Jschlings
Trigger Warnings: Transphobia
Mood Spoilers: Wholesome, Heartwarming
New updates start below 🔴🔴🔴🔴🔴
My best friend of 24 years (born a male) is now a transgender woman. I’m in love with her and not sure if I should tell her - 20 Aug 2022 with updates made in the original post until 13 Sep 2022
My friend and I (both 24 years old) have been best friends our entire lives, we’re practically brothers. Our parents grew up together, went to the same schools - so my friend and I were together ever since we were little babies. We’ve always had each other’s back, protected one another, cared for each other - when the whole world felt like it was against us, the both of us knew we were always looking out for each other. My friend is an amazing person, someone I can go to and trust completely. I’m blessed to have this person in my life.
My friend transitioned to a female a few months ago, she’s completely physically a woman. She’s been through hormone replacement therapy these past few years, seeing her becoming so much more happier is amazing to see. I’m absolutely proud of her! It’s beautiful to see my friend now be so free, being comfortable with herself and always having the greatest smile on her face. But I’m falling for her, and these feelings aren’t going away. I’ll admit that I’m in love with my friend, the friend I’ve know for 24 years is who is stealing my heart and I don’t know what to do. I don’t want to lose my friend, but my feelings of friendship for her are turning to romantic/sexual feelings & attraction.
After my friend transitioned, we continued hanging out and talking like nothing changed. We continued going out to clubs/bars, the movies, restaurants, playing video games - nothing changed, we kept doing what we always did. During this time is when my feelings began to change, I started falling in love with her. You know what attracted me? Her, the way she is. My friend is now acting like herself, acting free and full of life - always laughing, dancing and being goofy. It hurts me, because this is someone I grew up with and I’m afraid my feelings are going to push her away or make this awkward. Like always I’m insanely happy being with my friend, but my feelings for her are killing me right now every time we’re together again.
I’ve fallen in love with her true self, her true self is absolutely beautiful.
I’ve spoken to another close friend of mine about this, I just got made fun of. “Haha! You wanna fuck your bro, seriously?!” Is practically what I got. They didn’t understand where I was coming from, they didn’t understand what an insanely amazing person my friend is. This friend of mine feels it’s “creepy” and “nasty” I’m falling for my best friend. They also aren’t taking my friends transition seriously, which is another reason why they’re acting immature. All he did was make fun of me, so ever since then I haven’t spoken to anyone else about how I feel.
Also, aside from being scared of losing my friend, I’m afraid of what our families will think. What happens if my friend and I do end up together, and our families suddenly start to panic. I’m afraid not only ruining my friendship, but the friendship our parents have with themselves for many years. Both of our families were completely supportive when my friend transitioned, not a single negative comment. Everyone is proud of her, and the love our families have for her hasn’t changed at all. I feel I’m over thinking all of this, especially because being friends is very different than being in a serious relationship.
If anything, our families would be insanely happy we’re together and be so annoying hahaha. But I’m more worried on the negative response, which is why I believe I’m over thinking this whole thing.
Plus, if I plan to even confess my feelings for her - I have to do it soon. She’s always being asked out on dates, but she tells me she’s looking for the right person to spend time with. I feel this is my opportunity to confess, but I don’t know if I should. I don’t just want to confess how I feel about her, I want an actual relationship with my friend.
If any of you have some advice, please definitely share it! because I have no clue what to do. I’ll love to tell my friend how I feel about her, but I don’t want to lose or ruin our 24 year friendship. I also don’t want to make it seem that I’m falling for her just because she’s now a woman, I don’t want her to feel that way at all. What do you all think I should do? I’ll absolutely appreciate the advice/input, I’ll greatly appreciate it so much.
UPDATE#1: screw it! I’m going for it, I’m going to ask out my friend. It’s Saturday, 1PM right now - I’m going to see if she wants to go on a date tonight. First off, wow! Thank you for giving me the motivation! Reading your comments has made me realize I shouldn’t waste time, I need to go for it or I’m going to regret it. My plan is to take her out on a fun date, and I’ll confess my feelings during the date. I might even show her this post, as I literally poured all my feelings in this post.
She actually lives a few houses down the street, we live in the same neighborhood/street - that’s why we’re pretty much always together 24/7 every week. I’m going to message her to see if she’s home so I can stop by, and while I’m there I’m going to ask her out.
Wish me luck! I’ll continue to update ya’ll 😊
UPDATE# 2: I got a date tonight! I was insanely nervous walking to my friends house. but I can’t stop smiling cause wow, I actually got a yes from my friend. One issue I had was where the date was going to be, I had no idea. But I remembered she loves this 80s bar/grill that has karaoke every night and tacos, so that’s where we’re going. So tonight it’s going to be tacos, drinks, 80’s music and karaoke - sounds like an awesome date! ❤️
I told her pretty relaxed, I didn’t rush into it. Showed up, started talking like usual and that’s when I asked her. Told her I would love to take her out on a date tonight, that I’ve been wanting to ask her out for the longest time. I definitely tried to hide my face from blushing, because she had a huge smile when I asked her out. She’s even extra excited cause we’re going to her favorite place. I feel asking her out has made her comfortable to flirt with me, she started complimenting me and even kissed me on the cheek before I left. She definitely felt more “intimate” if that makes sense. She even said she’s going to get “extra pretty” for the date tonight. I’ll admit, I’m really looking forward to that. Although it’s impossible for her to get “extra pretty”, seeing as she’s already gotten already.
I’m still shaking honestly, lol. The shakes are more shakes of excitement. I’m gonna pick her in 2-3 hours, so I’ll definitely be getting ready soon. Haven’t gone on a date in quite some time so I’m really looking forward for tonight - especially with the date being the girl really love. I’m still nervous, but it’ll pass eventually.
I’ll keep you all updated! I’m not gonna leave ya’ll hanging 😊
🔴🔴🔴🔴🔴
Tiny UPDATE (7:05PM, Aug 20) : I’m heading off to pick up my friend. I’m insanely excited, but really nervous. I’m sure it’s going to go great! You probably won’t hear from me for quite a few hours, or till tomorrow morning. I’ll definitely reply to your comments when I return and continue to update ya’ll. For now, I’m off to my date! Wish me luck 🙏
Wish you all an amazing Saturday! Talk to you soon.
Tiny UPDATE # 2 (8:40AM, Aug 21): Hey everyone! So sorry I kept you all without an update, but the date actually ended at around 4 in the morning. All I’ll say for now is wow! What an amazing night it was. It was really incredible. I’m gonna get up and I’ll be posting the update soon! I wanna tell you how it all went. saw the comments how you all want updates, I definitely won’t leave you hanging without them 😊
UPDATE # 3 (12:24PM, Aug 22): Hey everyone! Hope you’re all doing great. Sorry for taking so long! I feel bad cause you all have been waiting all day yesterday for an update, I got a little too busy unfortunately. Had a family BBQ, so I was helping my dad set everything up throughout the day. I’m finally back, and here’s the update you’ve all been wafting for!
The date was absolutely amazing, i’ll even say it was the greatest night ever! Spending time with the person I really love, doesn’t get better than that. All this made me wish I had asked her out a long time ago, better late than never! I’m insanely happy I did ask her out. Like I said in the previous update how my friend was going to get “extra pretty”, wow did she look beautiful. She was breathtaking. Had a lot of butterflies in my stomach. She had a red dress on, wore a blue shade of lipstick and had her hair tied back. She looked incredible, the most gorgeous girl in the bar we went to.
My heart kept poundi…
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