Boyfriend’s holidays with female best friend

OneSassyRobin · 2025-12-30T14:41:52+00:00

I’ve been seeing my boyfriend for 9 months, we are both in our 30s but he is 3 years younger. When I started dating him I knew he had a female best friend (5 years younger than him). I found this weird from the off because I don’t do ‘opposite sex best friends’ in any way myself but ok, I thought I would give it a chance. Since we have been together they have gone on 1 solo trip together (booked before we were together but during when we were dating), 1 trip with a third friend there for some of the time but they shared a bed at the end of the trip which he only told me after (swore it was top and tail), and they booked in July a room with a double bed as part of a big group NYE trip (context, his friends are all 5 years younger than him so everyone going is sharing a double bed with someone, but the other people are sharing with their partners or they’re single). Said best friend had to drop out of the trip in about September so since then I received an invite to the trip but I only the other day realised what the initial plan must have been when I saw the pictures of the house. On top of this, they text all the time and she wanted to have a call on Christmas Day. I find it all a bit much considering my 1 male friend I speak to once a month and would never propose a holiday without his girlfriend being invited. it’s not that I don’t trust my boyfriend and I have met her briefly a couple of times too, but I think this is just not the behaviour of a mid 30s person in a committed relationship. WWYD?

Makemeanonymous · 30/12/2025 14:53

Texting all the time, going on holiday together and sharing beds? You are the third wheel in their relationship.

SmileyMoonset · 30/12/2025 14:57

A 28 year old man being “best friends” with a woman 5 years younger is odd for a start. How long have they been friends? Because 23 and 18 is icky.

I would also have a red flag that all his friends are 5 years younger. No friends from school, uni or work peers?

The sharing a bed with an opposite sex friend while in a relationship is ridiculous and I’d have split up with him asap.

9 months is nothing - you could surely do better than this.

zipadeedodah · 30/12/2025 15:01

If I was absolutely desperate for a man I would probably tolerate that.

But I'm not. So I don't.

Sodthesystem · 30/12/2025 15:18

Sorry but if he's only known her 5 years then the correct thing to do would have been to tone down the relationship with her a bit out of respect for his girlfriend. Any kind of trip away should never involve sharing a room. And shouldn't be just those two either (maybe exceptions can be made if they were childhood friends and you got to know her very well).

He's just not respectful.
And neither is she because I'd want to know my besties gf really well. I'd be extra careful to be clear with her me and him were just friends.

I wouldn't even call it out TBF, you can't teach people to respect you if they don't want to.

But if you want to give it one last try I'd be very clear with him that solo trips are not allowed. And that considering he's shown he can't be tested, he needs to start having some boundaries with other women and sticking to them, or you're off.

I'd also be inclined to message her 'hello Sarah, it's Connors partner here. Just thought I'd invite you round for dinner sometime if you fancy? I've obviously told connor that solo trips and stared rooms with female besties they've only had a few years are not appropriate. But that doesn't mean he has to lose you, just that he has to be a little more thoughtful with respecting as appropriate boundaries. I'm so glad he has a nice friend to talk to and not sone lager lout! And you're welcome to come visit us any time. We're having friends round in xyz infact if you fancy? Love - Cheryl'.

DoubleBoubles · 30/12/2025 15:20

You may as well end it now while you’re still in the early stages of the relationship
She will always be his priority and you will just become more and more resentful as time goes on or he’ll eventually end the friendship for you and then he will be resentful

He's not necessarily doing anything wrong but you don’t have the same views when it comes to friendships of the opposite sex. You both need to find a partner with the same views.

Just to add, I definitely would not like this and would not tolerate it at all from a partner and I wouldn’t expect a partner to tolerate it from me either if the situation was reversed!

TwistedWonder · 30/12/2025 15:22

I’ve got really close male friends but this is crossing boundaries imo. No need at all to share a bed - never heard of twin rooms?

It’s a big ‘no thanks’ from me

FMSucks · 30/12/2025 15:23

Just no. To me it’s irrelevant if it’s innocent or not, I would not be comfortable it so would not engage in a relationship with him.

Purplewarrior · 30/12/2025 15:25

Dump!

firstofallimadelight · 30/12/2025 15:25

I wouldn’t be keen why do they have to share a bed?
id talk to him and ask him if he’s prepared to change the friendship as it makes you uncomfortable. If he’s not you will have to consider wether you can accept it long term

Coconutter24 · 30/12/2025 15:28

SmileyMoonset · 30/12/2025 14:57

A 28 year old man being “best friends” with a woman 5 years younger is odd for a start. How long have they been friends? Because 23 and 18 is icky.

I would also have a red flag that all his friends are 5 years younger. No friends from school, uni or work peers?

The sharing a bed with an opposite sex friend while in a relationship is ridiculous and I’d have split up with him asap.

9 months is nothing - you could surely do better than this.

Where do you get the age 28 from?

Pollqueen · 30/12/2025 15:28

zipadeedodah · 30/12/2025 15:01

If I was absolutely desperate for a man I would probably tolerate that.

But I'm not. So I don't.

No, he's taking the piss and I wouldn't tolerate this level of friendship and my DP has a few close female friends, not this close though

Coconutter24 · 30/12/2025 15:30

Sodthesystem · 30/12/2025 15:18

Sorry but if he's only known her 5 years then the correct thing to do would have been to tone down the relationship with her a bit out of respect for his girlfriend. Any kind of trip away should never involve sharing a room. And shouldn't be just those two either (maybe exceptions can be made if they were childhood friends and you got to know her very well).

He's just not respectful.
And neither is she because I'd want to know my besties gf really well. I'd be extra careful to be clear with her me and him were just friends.

I wouldn't even call it out TBF, you can't teach people to respect you if they don't want to.

But if you want to give it one last try I'd be very clear with him that solo trips are not allowed. And that considering he's shown he can't be tested, he needs to start having some boundaries with other women and sticking to them, or you're off.

I'd also be inclined to message her 'hello Sarah, it's Connors partner here. Just thought I'd invite you round for dinner sometime if you fancy? I've obviously told connor that solo trips and stared rooms with female besties they've only had a few years are not appropriate. But that doesn't mean he has to lose you, just that he has to be a little more thoughtful with respecting as appropriate boundaries. I'm so glad he has a nice friend to talk to and not sone lager lout! And you're welcome to come visit us any time. We're having friends round in xyz infact if you fancy? Love - Cheryl'.

Edited

How do you know they’ve only been friends for 5 years?

SmileyMoonset · 30/12/2025 15:32

Coconutter24 · 30/12/2025 15:28

Where do you get the age 28 from?

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You are quite right, I misread. But still - why are all his friends so much younger. Icky.

arbielle · 30/12/2025 15:32

Girlfriend- it’s not you, it’s your boyfriend. Get a new one.

Coconutter24 · 30/12/2025 15:34

How long have they been best friends? For me my answer would depend on length of friendship. Best friends for a year then no I’d not be happy about it and probably say something but if they’ve been best friends for 10 years I wouldn’t feel I could tell him what to do or not do. I would still feel uncomfortable but I’d hope he’d have the respect for me to put the boundaries in place himself

Coconutter24 · 30/12/2025 15:34

SmileyMoonset · 30/12/2025 15:32

You are quite right, I misread. But still - why are all his friends so much younger. Icky.

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Thanks, I thought I’d missed some info somewhere. I don’t know how old they are but say he’s 33 I don’t think there’s anything wrong with having friends that are 28

Lavender14 · 30/12/2025 15:37

No op. You need to set clear boundaries but tbh you really shouldn't have to.

My ex had a pre planned holiday with his female bestie before we got together. I let it fly because it was planned and I did trust him but I was also clear that it wasn't happening again.

The fact he was hiding the fact they're sharing a bed means he knew it would make you uncomfortable and he was going to do it anyway. And that for me would be the deal breaker because not only does he not prioritise your feelings/boundaries, he will lie by omission. I agree with the pp who pointed out all his friends are much younger, it's all pointing to Peter pan syndrome.

I'd throw this one back op. I don't think I should have to teach someone how to treat me well, they should know how to do it.

OhShitImNearly40 · 30/12/2025 15:42

Well I’m worried! My best friend is a woman and I’m terrified of dating and telling any new partner about her.
She's such a good friend and we’ve supported each other through so many ups and downs the thought of holding her at arms length seems awful. We text all the time and chat on the phone most days. There is and will never be anything more than friends, and although she stays round mine one or twice a fortnight, we never share a bed.
OP, they might be friends like I am with my best mate…or not. We really can’t tell over the internet!

WrylyAmused · 30/12/2025 15:44

I have both male and female best friends.
I'm also bisexual - so according to many here, I guess that means I shouldn't be allowed to go away on holiday with a friend ever, and possibly wouldn't be allowed to have a close best friend either, as both would be allegedly disrespectful to my partner.

In reality, friends are platonic, and are not lovers, so it doesn't make a difference what sex I'm attracted to and what sex my friends are, and whether those two things are the same or different.
And in my relationships, there's strong mutual trust, so I don't need to police a partner or to be policed, because we trust each other.

I treat my friends of both sexes equivalently (and apparently even now, this is not acceptable to many, go equality(!) ) - so yes, I would go away on holiday with both, would happily share a room and a bed with both (platonic, yes, it's perfectly possible!), and don't think it's unusual to exchange Christmas greetings with my best friends on the day itself.

@OneSassyRobin if the best friend was male, would you have a problem with your bfs behaviours? If so, then speak to him about it.

If your problem is purely because the best friend is female, then what you're actually saying is either that you don't trust him (again, inquire internally to see why that is, and address it with him or yourself as appropriate), or that you feel insecure (and again, is the insecurity because of anything he has actually done (talk to him about it) , or is it simply a product of your own fears (work on it yourself).

ZenNudist · 30/12/2025 15:45

Dump!

TidyCyan · 30/12/2025 15:46

I dunno. I wouldn't be too happy about this. Why aren't they together - as in do you get vibes one's keen but not the other? Were they ever? Is she single?

wrongthinker · 30/12/2025 15:50

OhShitImNearly40 · 30/12/2025 15:42

Well I’m worried! My best friend is a woman and I’m terrified of dating and telling any new partner about her.
She's such a good friend and we’ve supported each other through so many ups and downs the thought of holding her at arms length seems awful. We text all the time and chat on the phone most days. There is and will never be anything more than friends, and although she stays round mine one or twice a fortnight, we never share a bed.
OP, they might be friends like I am with my best mate…or not. We really can’t tell over the internet!

See, I don't get this. If you're so close that you know a potential partner would find it uncomfortable, and you cannot bear the thought of being distant from her, then you're more than just friends. Why couldn't there be something romantic between you? Honestly, it sounds like you love her - why not try dating her? Sounds like no other woman could really compete, anyway.

As for the OP - yeah, just dump him. He's already chosen her over you.

OhShitImNearly40 · 30/12/2025 15:54

wrongthinker · 30/12/2025 15:50

See, I don't get this. If you're so close that you know a potential partner would find it uncomfortable, and you cannot bear the thought of being distant from her, then you're more than just friends. Why couldn't there be something romantic between you? Honestly, it sounds like you love her - why not try dating her? Sounds like no other woman could really compete, anyway.

As for the OP - yeah, just dump him. He's already chosen her over you.

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Because romantic relationships are completely different. She’s my best friend but I don’t fancy her, want to live with her or spend the rest of my life with her as a couple. She wouldn’t want any of that either.
I’d have thought it’s pretty obvious the difference really?

Lavender14 · 30/12/2025 15:56

OhShitImNearly40 · 30/12/2025 15:42

Well I’m worried! My best friend is a woman and I’m terrified of dating and telling any new partner about her.
She's such a good friend and we’ve supported each other through so many ups and downs the thought of holding her at arms length seems awful. We text all the time and chat on the phone most days. There is and will never be anything more than friends, and although she stays round mine one or twice a fortnight, we never share a bed.
OP, they might be friends like I am with my best mate…or not. We really can’t tell over the internet!

But surely this is just something you'd discuss with a partner and you'd agree fair boundaries around. I wouldn't worry about a guy having a female best friend as long as his behaviour around her was still respectful of our relationship. Which in ops case I would say it hasn't been as they've been hiding things and sharing a bed. It's not about keeping at arms length, it's about respecting a partner and their need to feel secure in their relationship and making space for both. I ended up pretty friendly with most of my exes female friends, there was only one I had an issue with and that's because of her attitude and behaviour towards me.

Spiffit · 30/12/2025 16:00

Most people wouldn't being okay with this. It's hardly a lifelong friendship he has there but clearly his priority. That's his choice but nobody is forcing you to be with him either. I'd throw him back as I absolutely could not be arsed with that dynamic.