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Original poster

Boyfriend’s holidays with female best friend

122 replies

OneSassyRobin · 30/12/2025 14:41

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?

OP posts:
TheThingOnTheIce · 30/12/2025 16:03

Throw this one back
wish I’d taken my own advice in my last relationship
I believe men and women can be friends but my last relationship they were obsessed with each other and it was down right weird from the start
trust your gut

Original poster
OneSassyRobin · 30/12/2025 16:08

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).

If he was bisexual and going on solo holidays with a single male friend that he texted constantly I wouldn’t think it was a good idea either. People can have friends, but where’s the line in stopping acting like you’re single?

OP posts:
Flintgranet · 30/12/2025 16:16

You don't like it, don't think it's reasonable and don't want it to continue. (I would feel the same.)

So dump him.

Original poster
OneSassyRobin · 30/12/2025 16:20

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?

She’s single. I asked him why they weren’t together and he just said it was never like that and he’s not interested.

My concern is that you never really know where things can go if you give them a chance to develop, so it’s respectful not to push the one-on-one time.

OP posts:
BeeHive909 · 30/12/2025 16:25

So this situation would be a no no for me . My partner has a best friend that’s female and a couple years younger than us. They’ve been friends though for over 15 years if not longer actually . Before we met he’d done trips with her but they always got separate rooms and I believe that and I know there’s no romantic attraction there. Infact she’s gonna be future best woman at our wedding. So it can and does work but in your situation definitely not: they clearly were sleeping together.

Pineapplewaves · 30/12/2025 16:25

I used to work with a woman whose husband had a best female friend with a similar arrangement. Three years into their marriage my colleague told her husband that she wanted a baby and it was at that point that he admitted he had been shagging the pair of them the whole time, that he didn’t want a baby with her and he packed his bags and left her for the best friend. The rest of us could all see that coming but work colleague believed her husband entirely that they were just friends.

I wouldn’t have gone on another date with him after his admission myself, that would be too much stress in my life that I wouldn’t want to deal with. I would set yourself free, dump him and find someone else that is entirely committed to you.

outerspacepotato · 30/12/2025 16:33

His priority is his best friend, not you. He sounds more emotionally invested and they travel together and share a bed and text all the time. You're the outsider in this threesome.

I'd be out of there but I wouldn't have stuck around for any of that.

catpigeon · 30/12/2025 16:36

He's shagging her

TheThingOnTheIce · 30/12/2025 16:36

Sorry if it’s already been mentioned but have you met this friend? My ex was very reluctant for me to meet her and it took nearly 2 years, didn’t have any issue with me meeting his parents / siblings/ other friends though . Huge red flag amongst a sea of other red flags .

MammaTo · 30/12/2025 16:52

It was top and tail - yeah okay!

Homegrownberries · 30/12/2025 18:57

Paraphrasing Princess Diana, there are 3 of you in this relationship.

Timeforaglassofwine · 30/12/2025 19:04

He is taking the piss. Its fine to have an opposite sex best friend but you have to have respectful boundaries. An opposite sex best friend can never work the same as a same sex best friend.

PopcornKitten · 30/12/2025 20:20

I agree that it’s completely inappropriate. Sharing beds (and as far as I’m concerned bedrooms) is a no go when you’re in a committed relationship. If the other person is ok with it then that’s up to you.
he needs to stop behaving as though he’s a single man.

wrongthinker · 30/12/2025 22:19

OhShitImNearly40 · 30/12/2025 15:54

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?

Show quote history

I think that your partner should be your best friend. I think if you struggle to put friendship and romance together, you're going to find relationships hard. And I very much doubt that any woman would want her partner to have a female best friend who he values more than her. So, good luck!

outerspacepotato · 31/12/2025 00:14

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!

@OhShitImNearly40,

You should be worried because most women want their SO to be their emotional partner in a relationship but you've already got your woman bestie in that role. You don't have emotional space for a life partner so that's not something you can offer. And you don't want to tell women because you know they'll see it as a red flag and stop seeing you if they want a serious relationship.

But OP's boyfriend has kept the fact that they bed shared on at least one trip from her. That's big. There's more he's hiding.

Bones101 · 31/12/2025 01:37

I don't even share with my best friend and he is a guy and he's also gay...

Please leave he's making a fool of you.

Nicewoman · 31/12/2025 18:15

OneSassyRobin · 30/12/2025 14:41

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?

Absolutely DUMP HIM! Without quoting Princess Diana when she said there were 3 of us in this marriage.

Are you nuts to put up with this nonsense? She texts him all the time, they share beds, they holiday together.

They are dating and shagging. Sorry. Friends with massive benefits.

You have to spell it out to him this is unreasonable.

imagine you had some gorgeous looking male friend, who texts you all the time, is loaded, brainy, big dick, you have holidays with him. Try seeing if your boyfriend is happy with this set-up.

Puffins4eva · 31/12/2025 18:16

Leave now

They are having sex

I'm sorry , the truth hurts but stop pretending this 'arrangement ' is ok .
It isn't

Laura95167 · 31/12/2025 18:16

My best friend is male has been since my teens. We text, go to the pictures, meals. Never have i ever planned a trip with a double bed for him and i. Never have insisted on a call or a particular day (especially Christmas) Never have i behaved like we are a couple and neither has he.

This isnt about her age. This is about them flirting with possibilities. She fancies him and he fancies her attention.

Throw him back.

Nicewoman · 31/12/2025 18:25

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!

You won’t ever have a partner.

No woman is going to put up with you sneaking off for chats with your female friend. What happens if you’re a dad? your wife will expect to put her first. Plus your best friend should be your wife, not some female friend. And want happens when your female friend gets a partner? How is her husband going to accept that when she says money is tight, but she’s just nipping out to the cinema with you, whilst she tarts herself up before heading out.

PrincessofWells · 31/12/2025 18:37

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

That message would be so inappropriate I don't know where to start. This is not about her, it's about your partner and you . . .

KimuraTan · 31/12/2025 18:50

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!

IMO men who are good friends with women would still shag then if they could. They just don’t because the woman doesn’t want to.

Not judging you at all - you might be the exception - but if I were the OP I’d either make sure the other woman knows the relationship rules or I’d throw the man back. This is unsustainable in its current shape.

Nicewoman · 31/12/2025 18:58

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ohyesido · 31/12/2025 19:03

This is not a set up that I’d be comfortable with.

MCF86 · 31/12/2025 19:06

The bit I believe least there is that they would top and tail. Who wants to wake up with big hairy man feet in their face?

I have a male best friend and we've slept in the same bed before, miraculously managing not to have sex, but I've not top and tailed with anyone since childhood sleepovers.