Last Updated on April 8, 2023 by Angela Vaz

Life has provided you with a beautiful opportunity.

And you really want to snag it.

You want to date this person.

But at the same time, there is a caveat.

Your friend has slept with them in the past.

So, how do you proceed? You want to move with caution because you don’t want to upset your friend and at the same time, you want to avoid it becoming messy.

In this post, I’ll talk to you about everything you need to know about dating someone your friend slept with.

There are multiple scenarios to consider before making this decision so let’s dive into each one and then talk about what to do in each case.

Let’s begin.

But before that really quick, get my free guide on how to really reset your life.

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1. If it was a serious relationship

if it was a serious relationship

If at all your friend had a very serious and committed relationship with this person and they were heartbroken over the loss, then I would suggest not dating this person at all.

Especially if you value your friendship with your friend and saw how devastated it made them feel about losing their ex.

It can bring up a lot of unwanted emotions in your friend seeing you two together and it might even make things very complicated.

You could lose your friend and maybe it’s not worth it.

2. If it was a 1-time hookup

If your friend slept with this person you want to date and it was not serious or it was just a few dates before they realized that they were not right for each other, then it’s completely okay.

There is no problem if there were no feelings involved and both of them parted amicably.

It’s alright for you to start dating this person.

If you are worried about the sexual relationship between them, you have to understand that it was in the past.

You are considering dating this person in the present.

You have no control over anyone’s past, so unless your insecurity is stopping you – go for it.

You aren’t doing anything wrong.

3. Their past bothers you

their past bothers you

You have to understand that everybody has a past.

When people have a past, it means that they weren’t afraid to live or fall in love.

They took chances – maybe some of them didn’t turn out that well.

But what matters is they tried and they’re still looking for love.

The fact that it didn’t work out between your friend and this person you want to date is a good sign – they were mature enough to walk away from something they knew wasn’t working.

Their past is in the past.

If your friend has no problem with you two dating and this person has no problem dating you, then nothing should stop you.

So, even if they slept together or still talk to each other, it isn’t a bad thing.

They’re simply adults who recognize that a relationship with each other won’t work out.

If you truly have feelings for this person or would like to get to know this person – go for it. Date them.

Dating isn’t a commitment – it’s data collection.

You both are getting to know one another – to see if you are compatible and share the same values.

So, don’t hesitate to date them.

If their past is bothering you to the point where you want your partner to NOT have a past, then you need to do some serious work on yourself.

4. Your friend thinks it’s a bad idea

Let’s say your friend dated them a long time ago and doesn’t have a problem with you two dating but constantly tells you that this person is bad news.

Tell your friend gently that you’d still like to date them to understand them.

You have the right to make your own choices.

So, if your friend is advising you a lot against dating them – listen with an open mind.

But at the end of the day, you get to choose whom you date.

Go on the date and learn for yourself what this person is like.

If all the red flags are there, then you can decide to not proceed to date them further.

But don’t allow your friend to cloud your judgment without giving them a chance.

Especially if it’s been a long time since they’ve dated.

People change, and perspectives change.

Allow room for people to grow.

5. How their relationship ended

how their relationship ended

If you know that this person ended the relationship badly with your friend – like they cheated on your friend or they were abusive, then the situation is entirely different.

In this case, I would suggest not dating the person at all but for 2 reasons.

Not only is it really disrespectful to your friend, but it’s also disrespectful to you.

You are only going to end up with heartbreak because this doesn’t sound a like a person who can commit to a long-term relationship.

If you feel the person has changed, I would still advise against it because you can risk losing your friend.

Dating a person that has hurt your friend so much is a way of saying that you don’t really care about your friend.

6. Talk to your friend

At the end of the day, you need to ask yourself what relationship you value more.

If you value your friendship more, talk to your friend and ask them if they are okay with you dating this person.

And then do what you feel is right.

This is not a cut-and-dry case because each situation is different with a whole lot of factors.

So you need to consider all of the factors before making a decision.

7. Your friend is immature

your friend is immature

There are some people that will sleep with a person and claim them for life.

They’ll tell all their friends that this person they slept with once is off-limits.

They don’t do it because they care for the person, they do it because they want to establish control and feel that they own the person.

If this sounds like your friend and you are sure that your friend slept with a person just once but doesn’t want anyone dating them – then you might have to seriously consider your friendship with this person.

It’s unhealthy and sounds like your friend is just being immature.

In this case, I would suggest doing what your heart is telling you to do and just proceeding to date the person.

If your friend ends the friendship over this, then it’s totally alright – you don’t need to feel guilty because your friend is being unreasonable and treating their ex like a possession.


I hope this helps you understand what to do in each case.

I know this situation is kind of messy and dating someone your friend slept with can put you in a tough spot, but I hope that the scenarios I’ve outlined help you understand what to do.

Let me know if you have more doubts or questions – I am happy to help.

Here are a few more posts to help you:

Angela is a 30 year old Illustrator and Blogger living with her 2 adorable labradors in Bangalore, India. She has a degree in Psychology and Human Relationships from the University of Toronto. When she's not writing her heart out or drawing, you'll find her sipping chai and reading non-fiction books.

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