Is it bad to date the friend of a former boyfriend?

Recently, I have found myself in an uncomfortable situation:

I have a small circle of good friends, all of whom are practicing Catholics. We get together on a regular basis for movies, dinner/drinks, etc. (Age range of these people is mid-twenties to mid-thirties.) A little less than a year ago, I ended a brief dating relationship (3 months) with one of the men of the group, “Rob.” We remained friends (probably an unwise idea); and before long, we were both spending time with our mutual friends again as though nothing had happened.

Then, a couple of weeks ago, one of my other male friends from the group (“Mark”) asked me on a date, and I went with him on a second date as well. When Rob found out about it, he was upset and (I think) hurt. Both Mark and I have since talked to Rob about it, and I think we are on reasonably good terms again. But I know that if Mark and I continue dating, we won’t all be able to hang out again as we used to.

So I guess my question is threefold:

  1. Was I wrong to go out with Mark, given the circumstances?
  2. Does it speak poorly of his character that he asked out his good friend’s former girlfriend? (or am I making it a bigger deal than it really is?)
  3. Is it just a bad idea all around to date within one’s circle of friends? As I think on it, I am not sure that it is worth the potential drama and awkwardness. If I want to keep things the way they are with my good friends, I would have to end things with Mark now before it goes any further. I really don’t know what to do.

I think the proper course of action in these types of situations can vary considerably based on many different factors (size of the group of friends, seriousness of the prior relationship, etc.)

My opinion is that a three month relationship is barely a blip on the radar. Simply dating Rob for three months does not give him perpetual oversight of who you choose to date in the future. I don’t see how it was wrong for you to go out on a date with Mark (unless Rob and Mark were like brothers and your relationship ended extremely poorly). Given the fact that you still hang out with him, it couldn’t have been that messy of a breakup.

That said, only you can discern whether or not it is a good idea for you. You cannot control Rob’s reaction (or the reactions of others in your group of friends). It could make things awkward. It could add to the drama. So you have to decide whether or not you think Mark is worth it. Is it worth the potential awkwardness if Mark turns out to be a good match for you?

You say that you ended the relationship with Rob. So to clarify, you broke up with him, right? How did he take it?

Yes, I did. The dating relationship was relatively short, but we were really good friends before we started dating, and he took it pretty hard. He was good about it, though–not angry, just sad.

EnglishTeacher said:

“1) Was I wrong to go out with Mark, given the circumstances?”

If they were best friends, I would hesitate to do it, but if they were just friends, no the old boyfriend does not get veto power over your romantic life. That said, don’t go on to date your way through your entire friend group. That would be weird.

“2) Does it speak poorly of his character that he asked out his good friend’s former girlfriend? (or am I making it a bigger deal than it really is?)”

There just aren’t enough amazing Catholic men and women out there for one to be too scrupulous about this sort of thing. You know how hard it is to find a good guy.

“3) Is it just a bad idea all around to date within one’s circle of friends? As I think on it, I am not sure that it is worth the potential drama and awkwardness. If I want to keep things the way they are with my good friends, I would have to end things with Mark now before it goes any further. I really don’t know what to do.”

Is Mark worth it? Do you like him that much? If so, go ahead. If you’re not serious, don’t.

If you found an outside boyfriend and started dating seriously, you would be introducing him to your existing friend group, so you’d still have the issue with being awkward with Rob. So I think it’s a problem that would exist as long as you are socializing with Rob, even if it weren’t a member of your friend group.

Maybe you should keep your dates with Mark separate from your group activities (not being secretive, just not being super demonstrative) until you figure out your relationship with Mark. Once you decide if you and Mark are serious, you can start being more of a couple at this group events. If it doesn’t work out, you won’t have been rubbing Rob’s nose in it unnecessarily.

Mark would have been wise to let on to Bob that he intended to ask you out, on the off chance that Bob had immediate plans to try to rekindle things with you, but it would have been small of Bob to expect that none of his friends ever date any of the women in the group that he has dated in the past, particularly when it was as short-lived as your dating relationship was. It has been nearly a year, after all. If you had been married for 30 years and Bob was now dead, Mark could have asked you out after a year had gone by! The death of a dream doesn’t deserve more than the death of an actual marriage.

That doesn’t mean it is unrealistic that Bob will find this hard to watch, but these things happen. You aren’t doing anything wrong. If you can’t live with seeing one of your friends dating a guy that you used to date, then you’re stuck keeping the people you date out of your social circle until you marry them! That is not a good alternative to being willing to go through a bit of transitory heartache. If Bob couldn’t take that possibility, though, he’d have been better off not dating you in the first place.

Keep those rules in mind as you start your relationship with Mark, though. The next “Bob” could be you. I’d say go for it. If you wind up getting the same treatment that Bob did, and find yourself the bridesmaid at Mark’s wedding instead of the bride, you’ll survive it. It won’t be the end of the world, and it is not worth taking the men you know well out of your courtship circle in order to avoid it.

Gotcha. It probably stings for him a bit then. Especially if he doesn’t have someone else in his life right now. Also, we don’t know how much he liked you, and guys who get dumped are a lot more likely to downplay their feelings to “save face” than to exaggerate them.

I think the best course of action would be to remain warm, friendly and generally welcoming to him. Don’t assume that you need to give him space. If he needs space, he’ll distance himself, and hopefully if that happens, he’ll soon change his mind. :slight_smile:

In and of itself, there isn’t anything wrong. However, the situation will invite awkwardness and drama. I know that is a “yes/no” answer… sorry I couldn’t be of any more help.

Pretty much–that is, if she is ready to find herself in what may be Bob’s spot, which is to say lovesick for Mark only to have to watch him marry one of her female friends from their social circle, there is no inherent moral repugnance in dating Mark. Hazardous in certain ways, though, yes. And yes, it would have been more sensitive of Mark to have given Bob a head’s up. It is worth watching for whether this was merely a mistake or whether it betrays an undesirable character trait.

In the end, it depends on what her risk and consequence tolerance is, wouldn’t you say?

Can we start with the word ‘friend’?

I agree with EasterJoy. Think about if this happened to you. I think that getting a “heads up” warning from some girl, in a group of FRIENDS, who was going to date your old boyfriend who broke up with you, would be the friendly thing to do.

The fact that Mark did not give a “heads up” indicated he wasn’t thinking like a friend, nor were you, I suspect. I doubt that anyone here understands what "FRIENDS’ means. (And it’s not defined by a TV series of the same name, or by a Facebook icon).

I suggest you learn about friendship, and responsibility first before considering dating anyone. I don’t mean to sound harsh but the issue in your thread title involves “Is it bad…” and the answer can only be discerned by whether this group is made up of friends or not. If it were just a bowling group or a discussion group, that might imply a looser bond than a group of friends.

“Friends” implies a certain amount of loyalty; “close friends” implies a tighter loyalty. And in both cases, dating someone who was once dating another person for three months would require good communication. Now what that ex-boyfriend or girlfriend does with their feelings and whether it disrupts members of that group of friends will be that individual’s responsibility. Perhaps no one spoke for fear he might get mad. But he is probably madder for finding out later; you can’t fix that either way.

Just file it away and learn for the future.

I think your question right now is where do your loyalties lie? and how do you know that your loyalties are a good guide to follow?. The group of “friends” may be a sham, the new guy might be a sham, or all of the above.

If you don’t date from among your friends and acquaintances, then who will you date? Strangers?

I think Bob is blowing this a bit out of proportion. I don’t see why Mark would need to check with him 9 or so months after you broke up when you’d only been dating for 3 months. Bob is not in charge of either of you. Do other people you know get a committee vote before they ask someone out?

Since you have both spoken with Bob now, I think you can move forward with your relationship - either continue dating or not. Don’t think you have to continue because you’ve stated to Bob that you are dating, but also don’t break up with Mark and then move on to Jeff, the next guy in the group.

The relationship with Rob was very short. I see nothing wrong with dating Mark. That said, of course it will be awkward for a little while, but Rob will eventually get over it if the relationship ends up being long term.

I have to disagree with the others who said that Rob should have asked Mark or at least given him a heads up. I did date within a circle of friends. The guys who gave a heads up to the ex’s ended up with more problems than they solved. First, the ex would sometimes object and an argument would result. Second, the girls felt that basically asking the ex permission to date took the girls wishes out of the equation and made them feel as if they were somehow seen as the property of the ex with no say so.

The bottom line here is that these are all adults. If a relationship doesn’t work out they should know by now that the ex is going to move on and date. If they cannot handle seeing the ex with someone new, friend or not, then they should not continue hanging out with their ex.

“Friend”. That can be a useless term when everyone has a different definition. Nice contribution Auntie A. Similarly, I think how people think of and pursue “dating” is also relevant.


I suggest the physical nature of your relationships with these guys is very relevant to your questions. Please understand, I am not making any assumptions or being critical of you.

MJJean said:

“If they cannot handle seeing the ex with someone new, friend or not, then they should not continue hanging out with their ex.”

Exactly. The OP is (given her lively social life so far) almost certain to become seriously involved with someone in the next few years, and if Rob wishes to continue to be her friend, he is going to have to deal with the prospect of seeing her with others and eventually married to somebody else. Likewise, the OP has to be prepared to deal with the sight of Rob being deliriously in love with a new girl or maybe even Mark in love with another girl and both of them eventually marrying and having families, perhaps even before the OP. Think about all the lovey-dovey smoochy-woochy stuff that you would prefer that they not do in front of you with the new girl, and don’t do that stuff with your new guy.

I feel like we get lots of advice here to “be friends first” (and it’s not bad advice), but this post is a reminder of the possible complications of dating within your social circle.

Best wishes!

A “heads up” and asking for permission are two different approaches. I favor the first assertion IF the group is truly a group of friends. If they are folks that just hang out together then maybe all is fair in love and war.

I do agree still that the words FRIENDS and DATING are important to be defined.

I would define dating as two people being together as a couple socially. Friends is a lot harder to define. Sometimes a friend is someone you are so close to they might as well be family. Sometimes a friend is someone that you spend time with here and there.

As for asking permission vs a “heads up”, I think the “heads up” is given when the relationship ends. When a relationship ends both parties know that they are now free to date other people wherever those people may be found.

It’s awkward but not “bad”. If you had already broken up with “the other guy”, then it was fair game for the “new guy” to ask you out. He didn’t need to ask for permission or even give the other friend the heads-up. He didn’t know if you’d accept and even if you did, he didn’t know how the date would go. He took a chance and asked you out after his friend had struck out with you. If you find yourself attracted to him and he’s a good Catholic man, don’t let the fact that you dated his friend deter you.

I know several people who are married to people who once dated their friends. These are marriages that have lasted decades and are still going strong.

DISCLAIMER: The views and opinions expressed in these forums do not necessarily reflect those of Catholic Answers. For official apologetics resources please visit