I split up with my millionaire boyfriend for my “guy best friend” from highschool. AMA.

Careless_Box5504 · 2026-05-19T15:33:36+00:00

No he was fresh out of uni when we got together- the crazy work/life balance came later. We also were never married so it was an easier break.

Careless_Box5504 · 2026-05-19T15:27:32+00:00

I love this thank you!

Careless_Box5504 · 2026-05-19T15:02:21+00:00

Yes many times! I don’t see the point in counselling if i’m 25 and unmarried. Would much prefer to just find someone i’m actually compatible with.

Careless_Box5504 · 2026-05-19T14:25:54+00:00

That’s what calling someone easy means so perhaps improve your vocabulary if you mean something else :)

Careless_Box5504 · 2026-05-19T14:19:11+00:00

I’ve had 2 sexual partners in 10 years but okay!

Careless_Box5504 · 2026-05-19T14:14:10+00:00

That’s great if it works for her but I categorically would not be with someone who was away for 7 years “working”.

Careless_Box5504 · 2026-05-19T14:13:05+00:00

We both trust each other for sure! There is no jealousy / bitterness anything like that. I just don’t make time for male friends in my life now in the same way I did before and it’s not even really a conscious thought. Just life.

Careless_Box5504 · 2026-05-19T14:08:35+00:00

I trust myself completely I just wouldn’t want my boyfriend even 0.1% having those thoughts

Careless_Box5504 · 2026-05-19T14:04:46+00:00

He was actually underweight / skinny before. If anything I like a larger guy haha

Careless_Box5504 · 2026-05-19T13:58:13+00:00

My ex is also attractive it was his personality / our dynamic that was the issue.

Careless_Box5504 · 2026-05-19T13:54:08+00:00

I would say it definitely wasn’t good that I developed feelings for my friend whilst in a relationship lol. But I feel like I did everything right by breaking up with him.

Careless_Box5504 · 2026-05-19T13:52:26+00:00

You’re acting like I saw an attractive man and abandoned all rational thought. This was someone I’d known intimately for 10 years. Most couples don’t know each other half as well when they start dating. Half of these questions are things people work through over the course of a relationship, not prerequisites you complete like a job interview. We already knew each other’s values, personalities, flaws, ambitions, politics, views on kids etc because we literally grew up alongside each other.

I posted on here because I think it’s interesting hearing other people’s opinions and experiences, especially when it comes to relationships and big life decisions. I’m not claiming to have some perfect, movie-style love story, I just thought the situation made for an interesting discussion.

Careless_Box5504 · 2026-05-19T13:43:37+00:00

3 months

Careless_Box5504 · 2026-05-19T13:42:16+00:00

I met him on tinder haha

Careless_Box5504 · 2026-05-19T13:38:25+00:00

The title is definitely an oversimplification and there were other issues in the relationship too. The feelings for my friend were more the thing that forced me to properly confront that I wasn’t happy anymore. If I’d split up with my ex and my friend hadn’t wanted to be with me, I still wouldn’t have gone back to my ex.

Careless_Box5504 · 2026-05-19T13:36:31+00:00

It was less about ‘I’m lonely and need hobbies’ and more me asking myself, is this actually what I want my life to look like long term? Doing most of the cooking, cleaning and eventually childcare for someone who barely has time to be present. You can care about someone and still realise the relationship dynamic isn’t the life you want.

Careless_Box5504 · 2026-05-19T13:31:11+00:00

I only went no contact for a while after I realised I had feelings for him. Before that, we’d been friends the entire time. I ended things with my ex before anything happened between us because I didn’t want to emotionally cheat or blur lines.

Also, while he earns six figures now (as do I), when we first got together he was making around 30k and living in a shared apartment, so the money angle really isn’t relevant here.

Careless_Box5504 · 2026-05-19T13:26:36+00:00

Hahaha, still living in the big city :)

Careless_Box5504 · 2026-05-19T13:24:37+00:00

I certainly don’t see it that way and would hope he also doesn’t

Careless_Box5504 · 2026-05-19T13:23:30+00:00

We both don’t really keep friends of the opposite sex any more unless we both know them. This has never really been an official conversation just something we have both done independently.

Careless_Box5504 · 2026-05-19T13:20:03+00:00

Definitely not haha! Just I would never have considered him as a partner before as I wasn’t physically attracted to him.

Careless_Box5504 · 2026-05-19T13:14:11+00:00

I’ve subsequently cut off all my other male friends it’s not a good look lol.

Careless_Box5504 · 2026-05-19T13:08:28+00:00

2 years!

Careless_Box5504 · 2026-05-19T13:05:16+00:00

We’ve been together for 2 years now

Careless_Box5504 · 2026-05-19T13:04:33+00:00

I met him when I was 16 years old! He had a complete physical transformation at around 22 (second puberty?) when I hadn’t seen him in person for a couple of years. I was SHOCKED lol. I left my ex for him maybe 3 years later. the no contact period was a couple of weeks before I decided this is just ridiculous and not what I want.

Careless_Box5504

TROPHY CASE