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

[Bezant]

1. 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?)

In my opinion, it speaks very poorly of his character that he didn’t talk to his friend about it first. That shows a lack of sensitivity and awareness of others’ feelings, and that’s something you should be on the lookout for. Does he frequently do things without considering or caring how it will make those close to him feel? Asking you out is not the problem. Not giving his friend a heads-up and trying to do this in the most delicate way possible is the problem.

I think there should be more benefit of the doubt given to Mark’s character. Most of us would agree that a three-month relationship is relatively insignificant, especially given the long time lapse since the breakup. It could be that Mark was just as surprised at Rob’s reaction as the OP for that same same reason; after all, he was quite casual around the OP for almost a year. Even if Mark knew Rob was more upset than he was letting on, it’s understandable that he wouldn’t share his intentions straight away. Friendship requires mutual honesty but there’s a time and a place for disclosure. The OP and Mark have only gone out twice. That sounds to me like they wanted to see if there was some kind of chemistry first, in which case it wasn’t really worth bothering Rob about a test drive.

 

[BlueEyedLady]

I think there should be more benefit of the doubt given to Mark’s character. Most of us would agree that a three-month relationship is relatively insignificant, especially given the long time lapse since the breakup. It could be that Mark was just as surprised at Rob’s reaction as the OP for that same same reason; after all, he was quite casual around the OP for almost a year. Even if Mark knew Rob was more upset than he was letting on, it’s understandable that he wouldn’t share his intentions straight away. Friendship requires mutual honesty but there’s a time and a place for disclosure. The OP and Mark have only gone out twice. That sounds to me like they wanted to see if there was some kind of chemistry first, in which case it wasn’t really worth bothering Rob about a test drive.

I guess it depends on what you are looking for. No, the truth is that Mark was probably not ‘obligated’ to talk to Rob first, but it would have been a really thoughtful, considerate, and kind thing to do. When I was dating, men who went above and beyond what they were ‘obligated’ to do for the sake of others were the ones that I was interested in, and I would recommend that everyone look for someone who does more than they have to for the benefit and feelings of others. In my book, it is a a red flag.

The conversation didn’t even need to be a big to-do. No sit down or heart to heart required, just a simple “Hey man, I know you and _______ were together for awhile. I just wanted to let you hear it from me first so that you aren’t caught off guard, but I’m planning on asking her out to get to know her better and see if we have a connection”. That’s it. Sure, it might be uncomfortable or awkward, but it would have said a lot about his character.

 

[Xantippe]

Bezant said:

“That sounds to me like they wanted to see if there was some kind of chemistry first, in which case it wasn’t really worth bothering Rob about a test drive.”

Right.

I guess it all depends how close Rob and Mark are too each other. If they are best friends, then they owe each other more.

BEL said:

“The conversation didn’t even need to be a big to-do. No sit down or heart to heart required, just a simple “Hey man, I know you and _______ were together for awhile. I just wanted to let you hear it from me first so that you aren’t caught off guard, but I’m planning on asking her out to get to know her better and see if we have a connection”. That’s it. Sure, it might be uncomfortable or awkward, but it would have said a lot about his character.”

But what if the OP and Mark don’t really hit it off after a date or two? Was it worthwhile to bring Rob into the situation so prematurely and perhaps bring the Sauronic eye of the group to focus on the new couple, who really don’t need that kind of pressure? Does every member of the group owe Rob this sort of heads up? Also, does your rule apply FOREVER? If Mark asked the OP out 5 years after she broke up with Rob, does he still need to give a heads up? 10 years? 15 years? 20 years? Unless Mark and Rob are great friends and together all the time, that sounds weird.

If these people are all such great friends, they can have dinner or a movie with each other without it becoming a federal case.

 

[InigoMontoya]

With the age group of you and your friends, this shouldn’t be an issue.

 

[LongingSoul]

This did actually happen within my group of youth group friends 25 years ago. Anne dated Damian for a few months but during that time she knew she would not marry him but had developed feelings for his brother, Chris. Quite soon after their relationship ended, she began dating Chris and they married eventually. As I said that was all 25 years or more ago and Anne and Chris are now grandparents. Damian married happily and the past is forgotten completely. Family get togethers are as normal and un-awkward as any other family would be.

It is awkward *at the moment *and the situation demands sensitivity on your part… but its just a passing phase. If Rob carries further than he should that is his issue to address somewhere independently.

I was born into a community of a maybe 1000 and that included families from farms around the district. Everybody knew everybody and was friends with everybody within their own age groups. You can’t afford to be precious in a small community. That’s just life.

 

[Bezant]

I guess it depends on what you are looking for. No, the truth is that Mark was probably not ‘obligated’ to talk to Rob first, but it would have been a really thoughtful, considerate, and kind thing to do. When I was dating, men who went above and beyond what they were ‘obligated’ to do for the sake of others were the ones that I was interested in, and I would recommend that everyone look for someone who does more than they have to for the benefit and feelings of others.

I’m not saying Mark was/wasn’t obligated to disclose, only that he might have had equal reason to consider it a bad idea.

Would it have been kinder for him (or the OP as a matter of fact) to update Rob beforehand?

Maybe, but that assumes Rob would have taken the information well and we have no reason to think that must be true. Actually Rob’s reaction suggests the opposite, in which case it would’ve been inconsiderate to distract him with what seems to be a trivial matter before it was necessary. Going beyond the call of duty has its merits within reason. Sometimes the preconcieved “nice” thing to do backfires in situations that demand more restraint. If Mark (or the OP) chose the latter, that hardly shows poor character.

But what if the OP and Mark don’t really hit it off after a date or two? Was it worthwhile to bring Rob into the situation so prematurely and perhaps bring the Sauronic eye of the group to focus on the new couple, who really don’t need that kind of pressure? Does every member of the group owe Rob this sort of heads up? Also, does your rule apply FOREVER? If Mark asked the OP out 5 years after she broke up with Rob, does he still need to give a heads up? 10 years? 15 years? 20 years? Unless Mark and Rob are great friends and together all the time, that sounds weird. If these people are all such great friends, they can have dinner or a movie with each other without it becoming a federal case.

Exactly. Sauronic Eye’s the worst.