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Relationship tips 7 questions to ask before dating your friend's ex

Most friendships last a lot longer than relationships, with few making it past the three month mark.

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Celebrities are always at it. Cameron Diaz and Kate Hudson both dated baseball player Alex Rodriguez and Justin Timberlake and still claim to be mates.

Jennifer Aniston and bestie Courtney Cox were both romantically linked with Counting Crows frontman Adam Duritz - and Katy Perry and Taylor Swift both had relationships with John Meyer (though that one did cause Bad Blood).

As for us mere mortals, my advice on dating a friend’s ex would be handle with extreme care.

Yes, you do have every right to date whoever you want and yes, what does it matter if they’re not going out anymore, but the thing is it does matter to most people, however illogically.

We all feel ownership over our exes, especially if the relationship was serious.

So if it’s a close friend that you couldn’t bear to live without, the short answer to ‘Should I date their ex?’ is a straight up ‘no’.

You really can’t help yourself?

Here’s what you need to know before making any life altering decisions.


1. Is it an acquaintance or a not so close friend?

The less well you know the person, the more acceptable it is to date their ex.

But I would still mention it to them, if it’s someone you see regularly and they’re still in contact with their ex.

Simply say, “Look, I just thought you should know that (their exes name) and I have gone on a few dates. I’m not sure if anything will come of it but I know you dated in the past and I thought you should know.”

2. Is it love or is it lust? Is this a passing fancy or a potential love of your life?

Most friendships last a lot longer than relationships, with few making it past the three month mark.

If it’s a good friend’s ex and you suspect your feelings aren’t likely to turn into the real deal, is it really worth potentially losing them over it?

3. If it’s a close friend, how serious was their relationship?

If it’s the ex of a close friend, I wouldn’t go there at all.

But what’s crucial if you are considering it, is how long they dated for and how serious their relationship was.

Anything over six months is tricky; if we’re talking someone’s ex husband or wife, especially if they’re sharing custody of children, you will probably be forced into a ‘them or me’ situation.

The only way you might be OK is if the relationship was never serious (they dated for a couple or weeks or a month or two) and stayed friends.

Websites like mysinglefriend has lots of people offering up their exes as potential love interests - though the crucial difference is that’s to strangers, not friends.

4. How old are you both?

Tracey Cox says we all feel ownership over our exes, especially if the relationship was serious

If you’re in your late teens or early 20s and part of a big group of friends, it’s quite usual to end up dating each other.

Once you’re older, it’s different.

You’re out there in the big, wide world, not hanging around with the same people all the time, so expected to find a bright, shiny new partner rather than recycle someone else’s.

5. Are you straight or gay?

An odd thing to ask, right?

Bear with me.

I asked lots of friends what they thought about dating exes before writing this and while all my straight friends seem very anti the idea, my gay friends weren’t that bothered by it.

That may be because the pool of people to choose from is a lot smaller when you’re gay or lesbian.

Gay communities are smaller and also more insular: everyone knows everyone and it’s inevitable that you’ll end up dating the same people.

6. Why did they split up?

If they mistreated your friend and left them not just broken-hearted but seriously messed up, why would you want to date them?

Substance abuse, sexual abuse, people who are violent or serial cheaters - date someone who traumatised a friend and you’re basically saying it was OK to hurt them badly.

Don’t kid yourself they won’t do the same to you. They will.

7. How do they feel about them now?

If the split was acrimonious and they absolutely loathe their ex, dating them means you’re questioning their judgement.

If you truly believe their version of events, why would you want to date them?

If you do, it suggests you think they’re lying or (possibly worse) think they behaved badly because they weren’t ever that keen on them.

Insulting whichever way you look at it.


Let me say once more, it’s never going to be the best idea you had, but if you honestly do believe their ex is your future love of your life, here’s how to have the best shot at keeping the friendship.

Don’t talk to your friend until you know the ex feels the same way about you, as you do them.

Especially if they’re still friends. They’re in the same position you are and even if you’re prepared to put the friendship with their ex on the line, they might not be.

Once you have had the conversation and made it clear you would date an ex of theirs, even if you don’t end up doing it, you have expressed intent.

The friendship has been irrevocably altered.

Now tell the friend about it.

Dating them secretly will make the whole thing even worse, so you absolutely must be upfront.

Before you talk decide whether you’re going to date the person even if they are really upset about it. If so, don’t word it like you’re asking permission because you aren’t.

What to say?

Start by saying you’d like to date their ex and really hope you’ll get their blessing.

Make it clear you didn’t plan for the attraction to happen or particularly want it to happen, because you value their friendship so much and would hate to lose it.

Explain that you’ve given it a lot of thought and don’t think it’s just a passing thing, otherwise you wouldn’t go there.

Give them time to process.

You’ll probably get one of three reactions: they’ll be genuinely happy you’ve met someone you really like and won’t care; they’ll be upset and may well walk out; or pride will make them say, “Sure, go ahead!” even if they don’t mean it.

Prepare for them to be uncomfortable rather than assume it will be OK and give them time to get used to it.

They might well come around once they’ve had time to think it through so don’t say anything you won’t regret, even if they do lash out.

Assure them you won’t be repeating anything they’ve told you in confidence.

You’ll be strongly tempted to gossip about the person you both know, each repeating what they said about you (never dreaming you’d end up going out) and be massively curious about how their relationship was and how you compare.

Avoid doing any of it - it’s usually disastrous - and avoid gossiping to your friend about them from now on, especially if it’s to complain.

If it all goes pear shaped

Don’t expect your friend to be there to hold your hand, like they normally do, if this person breaks your heart.

And don’t expect them to suddenly forgive you if they were upset and for everything return to normal just because it’s over between you and their ex.

You breached their trust by dating them: the damage is done.

Source: Daily Mail

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