Curious, would appreciate advice ..

[MrsMomoa2]

I am curious about a friendships .. obviously there is the Harry met Sally scenario (if you are old enough to remember that film!) but when does a friendship ..become more. Is the the amount of time they talk and how often, or if the conversation takes a 'cheekier' turn...
I am very confused about a situation which is why I am asking. My best friend for many years lives in a different continent, I know he is dreadfully home sick and is very lonely. We talk about everything daily (whatsapp/messenger) for hours .. just not one thing he rarely mentions .. his wife. Over the years we have had some (very) cheeky exchanges . I have realised I have got strong feelings for him and think I need to maybe stop talking to him... he has helped me talk through some dark times (I am separated)

When you start feeling uncomfortable, so now I suppose.

You are self aware enough to realise that you may be dancing around the line, so take a step back and reduce contact. He is not being respectful to his wife if he is having conversations with you that he wouldn't in front of his wife.

Well it's more than 'just' friendship if you're exchanging messages that would upset either person's partner by making them feel betrayed, threatened, devalued and generally shit about themselves.

So I would say you've crossed that line and need to own it. Either you decide you don't care enough about it being the wrong thing to do when he's in a relationship, so carry on the dynamic regardless, or you back away and stop.

When you say 'cheeky' messages I assume you mean flirting and / or sexual messages? Do you think your friend is actually a nice person if he's sending them and has a wife? I would think he was a prick.

Depends what you mean, cheeky doesn't mean disrespectful to his wife necessarily. If he is ok with her seeing the messages then it hasn't crossed the line for him but as you are struggling you need to rein back, reestablish the ground rules

This sounds like an emotional affair.
He is being disrespectful to his wife and so are you.
Have some self-respect and some morals and stop sending “very cheeky messages” to married men.

I don’t think there are hard and fast defining points for when the line is crossed, in terms of precise words said. After all, some people flirt in front of their partners and mean nothing by it, and the partner doesn’t mind. For others that would be a definite line.

I think if either of the “friends” start to feel uncomfortable, or the friends’ partners do, (or you suspect they would if they knew what was going on) then lines have been crossed, and some pulling back is needed, if not ending the friendship altogether.

Now is the time to stop it. Or pull back

when does a friendship ..become more

When you would feel embarrassed having the same exchange in front of his wife.

If you are already past that point, the best thing to do for yourself is to stop contact with him.

Fill your life with things and distract yourself. Good luck.

It sounds like you have come to rely on this guy as an amotional crutch, possibly when your marriage ended. Perhaps he filled a void that stopped you having to deal with the full brunt of your separation and being single.

Would you want a partner to message other women in a cheeky/flirty way?

Emotional*

From my experience as a life long single woman, most married men never mention their wives because they want to leave the door open to a fling. And they make it clear to me at some point they want a fling with me. I could by any woman, though. Most cast wide nets.

The few married men that mention their wives (usually over and over again) are being very clear to me they are married and unavailable. (and they flatter themselves because I have zero interest in them). They also don't make themselves available for long chats with A Woman Not Their Wife.

So, I think you need to step back - if only for your own sanity.

Do you find him sexually attractive? Could you see yourself in a relationship with him if he was single? If you can say yes to either of the above, or you think he might be able to, the friendship is likely to run into trouble and hurt someone.

I think you should cast your net way wider (I guess you're single as you said that you're separated). Put the shoe on the other foot, would you want your partner chatting daily to another woman on a different continent? It's a fools hope to think something positive to can come from this (1. He'll leave his wife for you aka you the OW, but then how can you trust him, and in the process ruin his marriage / family 2. Or totally reject you).

We have been friends for over 20 years, we lost contact for a while but started chatting about 5 years ago .. I was already single so he was not not an emotional crutch for that at all. It never started being flirty and just evolved .. there can never be a 'real' relationship he lives in a different continent and very unlikely to come home so I would never had set out for any of this and he was just a good friend for a long time. I have been more hurt by the actions of 2 female friends over the years who have let me down. But thank you for the kind words .. I am not a 'marriage wrecker' I do think he is unhappy but can't (won't face it but he is stuck there) but it can't be my problem.

I think if you let yourself get drawn in any further, you're going to end up feeling really badly about yourself if his marriage goes down the shitter and your "cheeky" conversations are one of the causes.

If he's spending hours online/on the phone talking to you in great depth about his feelings, then he's robbing that emotional energy from his marriage, which sounds like it's already in trouble as it is.

I would personally be very direct and honest and say "Look, I really love you as a friend, but I've realised our conversations are quite disrespectful to your wife because they are encouraging you to spend your emotional energy on a third party instead of your marriage. You should be able to discuss your loneliness and need for changes with your wife. If you can't, then that's a problem, and one you need to fix. But I need to step back because I'm not feeling good about my own actions in this."