I was working for a big company and I felt bad about the work I was doing. A friend (let's call him Tony) from my school (I am recently graduated) offered me a good position in his company. He does not own the company but is working hard here and is well respected. I accepted and I'm currently working there and I am very happy. On top of this I got back in touch with an old friend of mine (a girl, let's call her Sara) and introduced her to Tony. It appeared that Sara's best-friend (let's call her Alice) is the ex-girlfriend of Tony, and now we formed a friendly group of four which I really enjoy. The relationship between Tony and Alice is set, neither of them want more than friendship.

The problem

We hang out 1-3 times a week at night, because we all work during the day, and have a great time chilling outside, dancing and chatting. From the first time I saw Alice, I had strong guts feeling for her (she looks very attractive to me, and she is a very kind person, she loves animals and me too). At first I locked this feeling away and said, it's the ex of my friend I just can't let myself feel that for her. And everything was OK, the feeling was here but I was able to ignore it. But since the last 3-4 times we hung out, she started flirting with me in a very polite manner, full of compliments and really nice eye contact. I just can't handle the feeling right now and I'm really thinking about dating her, but I feel really bad about my friend Tony and I don't know how he'll react.

The question

How can I explain to Tony that I want to date his ex? I know I have to follow my feelings, but I'm really scared about failing the new relationship and destroying the group of friends we have now... I really want to know more about Alice, but I want to keep this group up. Any advice is greatly appreciated.

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    – Mithical
    Aug 5, 2018 at 21:01

2 Answers 2


Seems pretty straightforward to me: if Tony and Alice are happy being friends, why not just mention to Tony that you're thinking of asking Alice out? I'd be surprised if he had an issue with it, and honestly if he does I think it would be a bit harsh on his part - he can't be her friend and yet assert control over who she dates. If she's genuinely interested in you then as a friend he should be happy you may have a relationship opportunity.

In short: speak to him first (more as a courtesy than for permission), and if the conversation goes well, then ask Alice out and see where it goes. If the conversation with Tony does go badly, you need to decide if it's worth challenging his views and pursuing Alice or letting the matter drop.

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    Was planning to answer in a similar way, just want to add one thing. When you talk about this with Tony, start by asking him if he still has plans with Alice. Although OP already knows that "The relationship between Tony and Alice is set, none of them want more than friendship.", asking the question again shows that you are not trying to 'take her from him', but want to be sure he's over it.
    – user2848
    Aug 3, 2018 at 10:09
  • Thanks for the quick answer. Seems to be the most logical thing to do but didn't thought about that. I was thinking of just dating her or let it be. I'll be talking to him directly and will report back ! Any idea on how I can introduce to him this topic ? I know he isn't blind Aug 3, 2018 at 11:28
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    There are many ways you could bring it up with him. Something like: "So, you may have noticed I'm getting on really well with Alice. I was thinking of asking her out on a date, would you be cool with that? I think she's quite into me as well." Or any variation on that theme really. Aug 3, 2018 at 12:54
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    I agree with the comments and this answer. That said, it's not something you're asking for permission on, ultimately it's just a courtesy to float the idea by Tony before you go there. He might even have some immediately useful feedback like "Don't do it bro, she's a total psycho behind that pretty smile!". Aug 3, 2018 at 15:19
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    Had a quick talk with Tony and he was completely fine with me dating Alice. And she was ok too so everything is fine ! Thanks you all :) Aug 13, 2018 at 14:24

Will's answer is absolutely the correct one, but I wanted to add a different side to it.

As someone who has been in Tony's position, talking to him can make a huge difference. An ex and a friend started dating a few months after we broke up. They both, separately, came and spoke to me about it before they got together. It was much, much easier to deal with than finding out from someone else.

They're both still together 8 or 9 years later, and are still two of my best friends. I'm not sure they would have been if they'd hidden from me.

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