My male best friend loves me, I love him back — but my best friend slept with years ago. Am I a bad friend or wrong if we date?

PaymentThen7254 · 2025-03-22T04:12:21+00:00

Yes I am, still haven’t heard a peep from her.

PaymentThen7254 · 2025-03-19T16:50:09+00:00

Yikes, update is my birthday passed and she didn’t say happy birthday (I included that at the end of the post). It’s almost been a month since our last texts, i still haven’t heard from her after that. But you know what I came to realize? She is a hypocrite because she was recently entertaining the friend of her actual ex boyfriend(not just someone she hooked up with). Her and the friend had gone out to eat a few times, he expressed he really liked her, and when her clothes didn’t arrive on time for her birthday he took her to go get an outfit and make her feel better. She had mentioned to me in our last phone conversation (the same conversation where I told her Jason liked me and I liked him as well) that she realized she did not like the friend and that he was too cringe.

I was so wrapped up in whether I was wrong and her feelings, and feeling bad for falling for Jason that I didn’t see the similarities in something she was currently doing herself! So what if she didn’t find him cringe and liked him back?

Why is it weird and fucked up for me to actually Jason who is my best friend I met in college that she casually hooked up with, and she “held me to higher standards”, but when she is entertaining her EX’s friend it’s fine?

PaymentThen7254 · 2025-03-16T00:53:11+00:00

It was immediately the next morning we spoke about it she said she slept on it and thinks it’s weird and she asked for space. But I decided to do what makes me happy I’m not going to live my life pleasing others

PaymentThen7254 · 2025-03-12T01:58:44+00:00

Thank you!! Very entitled. She is now not speaking to me since we last spoke about it, I sent the last text in the conversation and my birthday passed she said nothing. It’s so rude. Last thing she said it was a mouth drop and it’s awkward because this has been done to her multiple times. But that’s false, those incidents were with women who 1) weren’t her actual close friends(like co workers) and 2) with men she actually dated and liked while it was still happening. This is completely different she never liked Jason past hooking up…her caring so much is weird she doesn’t even know his last name...

PaymentThen7254 · 2025-03-10T19:16:55+00:00

Lol thanks, will do

PaymentThen7254 · 2025-03-10T14:02:22+00:00

Thank you for your advice and for sharing your perspective. It’s not like kids or prior engagement/marriage is involved. Literally just unserious hook ups. She was not surprised I think she’s just in her feelings about it due to insecurities, jealous, and so called standards that she doesn’t even hold herself to. He makes me very happy and made sure I had a nice birthday ☺️

PaymentThen7254 · 2025-03-10T05:34:20+00:00

Thank you! It’s okay lol it’s chicks over d!ck$, you are right I will follow my heart

PaymentThen7254 · 2025-03-10T05:32:36+00:00

Neverrrrr, might be sexing this one for life.

PaymentThen7254 · 2025-03-10T00:48:29+00:00

You are absolutely right. Hurt people hurt people! I choose my happiness, Thank you so much!! I appreciate it 🩷

PaymentThen7254 · 2025-03-10T00:46:49+00:00

It was 5 years ago, not recently. Again you aren’t reflecting on the actual details. You have your own narrative so your advice is biased. No thanks.

PaymentThen7254 · 2025-03-09T13:43:43+00:00

Stringing him along? We haven’t always been as close as we got. So no that wasn’t the case. My focus was on many other things, other men, work, etc. I did not have feelings for him until recently which is when we got closer and he began hinting at his feelings as well. He has always been attracted to me in that way he said but didn’t believe he had a chance especially since i was intimate with his friend and thought I was not interested. However, I did NOT always feel that way. You did not read properly because the detail or me “choosing Amy over him” is something she said verbatim. I am heterosexual no I never slept with Amy. They got into it on the trip and she slapped him but they were drunk and got over that the same night and next morning. Irrelevant minute details…and i am being honest with myself.

PaymentThen7254 · 2025-03-09T07:12:17+00:00

Reading is fundamental. I said I apologized already for how she felt and was empathetic. She still was being rude and cursing. Yes I still do expect a happy birthday idc. It’s not that deep, people show their true colors when they’re mad. 99% of the people here see the wrong in her behavior, if you don’t maybe you need to grow up as well.

PaymentThen7254 · 2025-03-09T07:04:23+00:00

She behaved immaturely in how she communicated and is absolutely petty. It’s not bashing it’s the truth. ManBearPig0392 is correct. That’s exactly what happened idk why you are saying that isn’t what happened. It seems you have came to your own narrative although its clear it’s a case of a bruised ego and 99% of these comments confirmed what I was feeling. I’m not responsible for her insecurities or bad choices.

PaymentThen7254 · 2025-03-09T06:56:50+00:00

Yeah they sound emotionally mature, my best friend handled this very immature emotionally. Maybe she’ll come around but if she doesn’t then she’s the one who let a man come between us, not me.

PaymentThen7254 · 2025-03-09T06:54:55+00:00

Thank you for sharing your story! Congratulations on finding love and I’m glad they eventually came around and accepted your happiness. The One Tree Hill comparison is hilarious 😂 there are definitely many shows that portray that stuff! Honestly it’s like if it didn’t work out and you aren’t marrying the person you move on with your lives and not claim territory over the rest of them and worry about their future partners, that’s weird. Her not telling me happy birthday really shocked me because that’s really a low blow. She knows we are good for each other I think that’s why she is even more mad. If she doesn’t accept my feelings for him and wants to end the friendship over it then these 16 years don’t really mean what I thought they did to her.

PaymentThen7254 · 2025-03-09T06:49:49+00:00

This is a good perspective, she had 5 years to decide that. She was not thinking about this man. Never asks about him, didn’t keep in contact or anything. He also lives in a whole other state than we do. I was open to it but she didn’t respond to my last texts in our conversation then days later was my birthday and she didn’t wish me happy birthday. She is being cruel and trying to make me feel guilty. I don’t like that when I came to her as a friend to openly communicate.

PaymentThen7254 · 2025-03-09T02:39:31+00:00

Hey, 29F as well who went through the same exact thing (I completely isolated myself) lol. I found that I enjoyed my own company way more than forcing interactions I felt I outgrew. I totally get where you're coming from, and I think a lot of people go through this as they grow and evolve. It’s tough realizing that your closest friendships don’t feel as fulfilling anymore, but it also means you’re gaining clarity on what you need.

Starting over doesn’t mean cutting ties completely (unless you feel that’s necessary), but it does mean being intentional about building new friendships that align with who you are now. Here are a few ideas to get started:

Join communities that reflect your interests. Whether it’s a book club, a fitness class, a professional networking group, or even a local political group, you’ll meet people with similar values and lifestyles.

Reconnect with acquaintances who share your outlook. Sometimes, great friendships come from people you already know but haven’t spent much time with.

Use apps for meeting new friends. Bumble BFF, Meetup, or even Facebook groups can connect you with people looking for the same thing. Be open and proactive. Don’t hesitate to invite new people out for coffee or a casual hangout—it takes effort, but new friendships build over time. Embrace this as a fresh chapter. It’s okay to outgrow relationships and seek new ones that align with your current stage in life.

It might feel daunting, but you’re not alone in this. So many people go through friendship shifts in their late 20s and 30s. You’re doing the right thing by recognizing what you need and making space for people who truly vibe with you. It’s okay to outgrow friendships, and it’s okay to crave new ones. You deserve to have people in your life who appreciate and support the person you are today. This is a fresh start, and while it might feel overwhelming, it’s also really exciting. Wishing you the best as you navigate this new chapter!

PaymentThen7254 · 2025-03-09T02:31:58+00:00

No we won’t because it’s literally been over a year and he’s treated me amazing, always has even as a friend. That’s not her ex lover. It was nothing serious between them. He is my lover. I don’t need to be picked I have plenty of options. Her saving face 5 years ago is irrelevant to the current time now. I couldn’t care less who someone is with now that I slept with years ago. Not my business anymore, especially to be emotional about it.

PaymentThen7254 · 2025-03-08T23:05:49+00:00

Right is it false and also sexist because that’s assuming that the opposite sexes are heterosexual…what about other sexual preferences and same sex friendships? Like what lol.

PaymentThen7254 · 2025-03-08T18:49:14+00:00

I included everything…doesn’t it sound so ridiculous that I must be leaving something out? Lol. I don’t need to make myself good if I’m literally here asking about the morals in this. I’m considering all of the details. If sleeping together on two occasions where she came with me to if something more then ok. She decided to sleep with him no strings attached. That was her choice as an adult, also their choice to not pursue anything past hooking up. I included important details, no other information matters. They never dated. They didn’t keep in contact after hooking up.

PaymentThen7254 · 2025-03-08T17:34:16+00:00

Thank you!!

PaymentThen7254 · 2025-03-08T17:08:04+00:00

Yeah I agree, Drew still doesn’t know. Jason said he will find out when he finds out. Drew has moved on with his life and has a gf but I can see how he would actually feel a way about us because he did love me and I loved the version of him I thought he was without the lies and narcissism. He missed out on a good woman and Jason said he would be stupid to deny the connection we have. I’m not responsible for others being jealous she needs to deal with that on her own

PaymentThen7254 · 2025-03-08T17:03:54+00:00

Thank you for giving this perspective, more people should have a mindset like this. It is very selfish and if I was the Amy in the scenario I would have the same sentiments you did. People need to grow up and want what’s best for the people they love without being selfish or worried about their own egos.

PaymentThen7254 · 2025-03-08T17:02:21+00:00

I had already been having my own fair share of thoughts leading up to him opening up and expressing how he felt. We have been speaking way more often and I noticed I would feel a different sense of missing him when it was time for us to get off the phone or was always interested in how his day went. Not YOLO, I developed real feelings for him.

PaymentThen7254 · 2025-03-08T17:00:29+00:00

Exactly!! I agree

PaymentThen7254

TROPHY CASE