Dating a friends ex
June 22, 2010 12:12 PM   Subscribe

I am dating the ex-boyfriend of a (distant) friend of mine. Do I need to tell her?

When I was in college, I dated a nice guy, Will, for three years. His mom, Jackie, dated James for seven years total; a time line that covered before and after our relationship. The four of us hung out together a lot, movies, dinner, holidays. We got along well, and his mom was especially nice to me.
Ten years later, I ran into James at a party. We sat down to catch up, and ended up spending the evening together. He asked for my phone number, and we went out again – and had a blast. We’ve seen each other 2-3 times a week for a few weeks now.
Not long after the party, I ran into Jackie at the grocery store. We exchanged phone numbers and made plans to get together, but she flaked. I got one phone call in apology, and haven’t heard from her again. I never called her back. (getting flaked on is a pet peeve of mine, it will take me a while to forget it.)
James will be 50 this fall; I am 32. I don’t want to get married to this guy; in fact, I don’t think I want to get married at all. But, I can imagine myself dating James for a while.
To complicate things, I moved into a new neighborhood, and found out that Will is now my neighbor. He was out doing yard work with his wife and kids as I drove by, and I did a double-take. I stopped to say hi for a minute, but Will looked uncomfortable. It seems he knew I had moved in and didn’t know how to handle the situation.
As small as this town is, I know one day, I will be out with James, having fun, and will run into Will and his family, or Jackie, or both. I am cool with dating an older guy; I’ve never done it before, but its working out so well with James that I’m comfortable. But how do I prepare for the eventual ‘oh!? Are you guys… on a date?’ that I know is coming?
My mom and best friends are fine with my dating James. The consensus is, if I was 16 and he was 36, or even if I was 22 and he was 42, it would be a little weird. My mom says I am mature enough to date someone older, and ‘life is too short’ to NOT go out and have some fun – and I agree.
James is also still in contact with Jackie, occasionally. Should I ask him if he told her? Or if he’s seen her lately? I'm pretty happy dating James, and we’re having fun. I just want to know what to say if Jackie starts screaming at me in a parking lot or something.
There is also the possibility that Jackie may call me and ask to get together, which I would like to do – I’d like to hear what she and Will have been up to for the last ten years. What do I say if she asks me if I’m seeing anyone?
I’ve never dated a friend’s ex before. Years ago we were all pretty close. Am I making a big deal out of nothing, thinking about old times? Do you foresee any potential problems that I haven’t considered?
posted by anonymous to Human Relations (14 answers total)
I think there's definitely an "ick" factor here --- I felt it as I was reading your question --- so you can expect Jackie and Will to think this is a bit gross and to tell you that. But your response to any objections seems like it could be pretty simple ... "we've all moved on, James and I are adults, and we are free to date whomever we wish to date. Have a nice life."
posted by jayder at 12:17 PM on June 22, 2010 [1 favorite]

And I think the title for this question is best phrased not as, "Dating a friends ex," but rather as, "Dating an ex-boyfriend's mom's ex."

Dating a friend's ex is not what's going on here.
posted by jayder at 12:19 PM on June 22, 2010 [29 favorites]

I think you are overthinking this quite a bit. There's no reason to assume Jackie or Will would care if they knew you were dating James, and it's not your concern even if they do have an issue with it. Just have fun and stop worrying about workshopping other people's prospective hangups.
posted by joelhunt at 12:19 PM on June 22, 2010 [1 favorite]

It is possible for you and James to have a discrete casual relationship, given that you are not planning to marry. As for people seeing the two of you together, you can always claim that you are having a Platonic friendhsip, if the person asking is likely to be overly judgmental about it. You sex life isn'[t necessarily any of their business anyway.
posted by grizzled at 12:20 PM on June 22, 2010

Just let it be and if who you're dating dating comes up in your next conversation with Jackie, tell her what's up. If she asks you about it, don't lie. Otherwise, just relax, date this guy, and enjoy yourself.

I just want to know what to say if Jackie starts screaming at me in a parking lot or something.

If someone is shouting at you in a parking lot you, especially if it is about you dating their ex-boyfriend, you calmly walk away, plain and simple.
posted by griphus at 12:21 PM on June 22, 2010 [3 favorites]

Am I making a big deal out of nothing, thinking about old times?


Do you foresee any potential problems that I haven’t considered?

If anyone else has a huge problem with this, they are reacting immaturely and probably not worth your time.

Tell James that you bumped into Jackie and to Will recently and ask them what they've been up to. You all knew each other before, so it's a totally natural conversation and needs not be a big deal.

If you meet with with Jackie again (like you make plans), don't not tell her you're dating her ex. It shouldn't be a big deal, but you leaving it out makes it into something it's not.

How do I prepare for the eventual ‘oh!? Are you guys… on a date?’ that I know is coming?'

Do you really know this is coming? Maybe I'm just a big old "repress everything" small town Midwesterner but this seems like a really weird line of conversation.

Be honest and mature with everyone and this shouldn't be a thing.

Good luck.
posted by MCMikeNamara at 12:23 PM on June 22, 2010

She broke up with this guy ten years ago? You broke up with her son earlier than that? I don't think either of them has a right to be annoyed or have an issue with you guys dating each other. It's none of their business.
posted by IanMorr at 12:26 PM on June 22, 2010 [5 favorites]

If Will somehow knew you moved into the neighborhood, maybe he also somehow knows you are dating James.
posted by rabidsegue at 12:29 PM on June 22, 2010 [2 favorites]

I know some people think it's an unwritten rule that you have to ask a friend for permission before dating their ex, but I've never understood this. (I'm going to sidestep the question of whether Jackie is best described as your "friend.") I've been in the same boat and didn't mention it to my friend (the ex-boyfriend of my then-girlfriend). I acted the same toward him as I did toward anyone else: he found out when he found out. It naturally came up in conversation at some point, and I just disregarded the prior relationship between the two of them unless it happened to be particularly relevant to the conversation. Their relationship doesn't matter anymore -- it doesn't exist. The existing relationship is what matters.

And when it's been a whole decade since the prior relationship ended, you really have nothing to worry about. By that time, it should be assumed that everyone is completely over the past relationship.

Your specific situation is unusual: you're dating your ex-boyfriend's mom's ex-boyfriend. But doing something unusual does not mean you're doing anything inappropriate or that you have some sort of obligation to disclose the fact to certain parties.

A lot of the details you've included -- what various people might think about the age difference ... whether you would want to get married ... etc. -- don't seem relevant to your question. I'm not complaining about how you wrote up the post; I'm just saying you can stop worrying about all that.

"James is also still in contact with Jackie, occasionally. Should I ask him if he told her?" Considering how curious you seem to be about, why wouldn't you ask him? I don't see why you'd feel the need to get the go-ahead from AskMetafilter before having a natural conversation with your boyfriend.

Live your life according to what you want to do, not according to other people's opinions.
posted by Jaltcoh at 12:33 PM on June 22, 2010

I agree with others that if they have a problem with it, they need to sort that out privately and it's not up to you to adjust your relationships to make them feel better.

Having said that, don't push your luck. If/when Jackie calls you, I think it would be courteous to advise her over the phone about your new beau and ask her to decide if she still wants to get together - and don't be too surprised if she doesn't.
posted by cranberrymonger at 12:45 PM on June 22, 2010

You are making a big deal out of nothing. You are concerned about what people you haven't had contact with in ten years think of your dating habits? Who the heck cares what they think?

Will is probably acting all weird because his ex-girlfriend moved in next door and he thinks his wife might have a problem with it. Sure, he might be even more weirded out that his ex is dating his mom's ex, but again, who cares what he thinks?
posted by crankylex at 12:46 PM on June 22, 2010

Seems like this would be kind of an easy conversation to have with your boyfriend: "Hey, guess who lives down the street from me? Remember Jackie's son Will? He's married now (insert a bit of blahblahblah about Will)... Oh, by the way, he seemed a little uncomfortable when I stopped to say hi. Did you mention to Jackie that we are going out? Did she seem ok with it?"

Finding out what, if anything, he said to Jackie would be a good first step towards easing your mind. And if James hasn't told Jackie, maybe if he knows you are a bit apprehensive about the situation might prompt him to mention it to her.
posted by Serene Empress Dork at 12:53 PM on June 22, 2010 [1 favorite]

I think that it's clear that everyone is well past the statute of limitations for getting this okayed by any of the exes.

However, given that it seems inevitable that this will be known to Will and Jackie, I think it might behoove you to proactively ensure that your relationship with James is mentioned to at least Jackie. Not because you need their permission, but just in deference to what was once a close friendship.

Yes, ask James if he's mentioned it to Jackie, and perhaps encourage him to do so. Or if she calls and you two hang out, yes, let her know. Same with Will. You can likely accomplish a lot of goodwill with Will and Jackie a drama free "heyyy, just didn't want you to be surprised and feel weird. Let's not feel weird. Is everything cool?"
posted by desuetude at 1:42 PM on June 22, 2010

I live in a college town where all the regulars know all the other regulars. I have an ex who is now married to the ex of my husband. The lady who babysits for our former partners is also our friend and neighbor. As far as I know, everyone wishes everyone else best of luck and a happy relationship. Granted, we all just realized that the relationships weren't working and it wasn't like we just traded or anything.

The way we deal is by just being polite. Happy to bump into them, but we don't seek out visits. Polite, how-are-you-doing conversation when it's called for.

Stuff happens. Just be nice and polite. Talking about it with your current guy to make sure you're both on the same page is always a good idea, but this isn't something to freak out about.
posted by lilywing13 at 10:42 PM on June 22, 2010

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