Perfect response, Dan.
If you can't trust him with a lifelong friend, you just don't trust him.
Love Dan's response here. I truly don't get straight people and their inability to be friends with exes. I'm friends with one of my long term exes (we don't speak much because we broke up a long time ago) and not with the other one (bitch is crazy).

But I'm still friends with people I dated before and between those two. In fact, I had to make sure I called one of my ex boyfriends last fall (we dated in the late 90s!) to tell hm my mother died. He and she got along famously even after we broke up.
Fuck, where was this advice 6 months ago! WWDD please listen to Dan, he is so right on this one! Ex or not, deposits or not, you have to be able to trust your partner. If you don’t think you can, then end the relationship. My friends told me with complete confidence that my BFs relationship with his bestie was inappropriate, and I behaved accordingly. Jury is still out on whether I can repair the damage to my relationship. Don’t be like me, tell him to have fun, and don’t act distrustful! You will regret it!
I would focus on one bit of information Dan didn't in his response. WWDD's boyfriend was married for 25 years, dated his friend for 1.5 years, and has dated WWDD for 8 months. Conservatively, that makes him at least 52, which is a long time to be lifelong friends. They're not horny teens or twentysomethings. WWDD's boyfriend and his friend may have become lovers if for no other reason than the inevitability of exploring a romantic relationship with someone with whom they shared such a long, positive history. My guess would be that having realized that they're better friends than lovers, this relationship was throttled back to friendship, which makes me think there is little likelihood that WWDD's boyfriend would actually cheat on WWDD with his friend.

Moreover, if WWDD's boyfriend's parent's and his friend's parents are still alive, they must be about 80, if not older. So the parents have been friends for well over half a century as well. WWDD is not going to rupture those connections for a woman he met 8 months ago.

One other point to emphsize, at heart WWDD's worry isn't the trip, it is getting replaced by a woman who knows her boyfriend better and longer than she does. WWDD should express her fears to her boyfriend, but she should not make this a contest between herself and his friend.
I think, by the time you are in your 50s, you get to treat women with who you were/are-still attracted to as an actual friend without the ever looming threat of you fucking them hanging over your head.

I mean, that's the real question, right? "Can my boyfriend of 8 months be around a woman without fucking her?". If he were 25, well maybe your concern is a little more realistic. I've actually done this trip, with my then-girlfriend going apoplectic that my BFF (a gay woman) would be on the trip with me. We broke up until maybe 6 months later, but in retrospect that should have been the last straw. I'd advise the LW that she's probably behind the lifetime friend in the pecking order, if he's forced to choose between you and his ex, he'll probably choose the Ex.
@3: Mike Friedman, this is not an "all straight people are crazy insecure control freaks" issue.
I'm straight and still friends with all but 2 of my exes.
On a personal note, I had girlfriend who could not abide my friendship with a woman with whom I had broken up two years earlier, and had no interests in ever dating (or being sexual) again. But I wanted that friendship. My friend is nice and didn't deserve to be dumped at the behest of a jealous girlfriend. Friends are hard to come by as you get older, and if one happens to be someone with whom you previously had sex, so be it. (And life-long friends aren't something of which you dispose.) At any rate, that friendship came between my girlfriend and I, and that jealously was a factor in making me re-evaluate whether I wanted to continue dating.
Dan, great advice. The letter sounds as if the LW is looking for permission to be jealous and to give her fairly new BF an ultimatum. Ultimatums. Well, we all know how well those go over with BFs, especially new BFs!

Just a couple of observations/thoughts...

(1) The LW refers to her BF's once-in-a-lifetime trip as scheduled for over "spring break." This makes her sound young or at least significantly younger than her BF (see #2) and insecure. (I suppose she or he could work in academia and therefore still refer to a vacation in early spring as going to happen over "spring break.") Or perhaps her insecurity is because there is a considerable age difference between her and the BW and his friends? This brings me to: (2) her BF was married for 25 yrs prior to his 1.5 yr relationship with his ex-GF. He is, therefore, probably at least 44.5 yrs old. He and his friends are in a established friendship. At least one of the friendships (the one with his exGF) predates his former marriage. The LW is a newcomer and is perhaps feeling like an outsider, hence, the insecurity. This is not unusual and is understandable.

Other questions: Does the LW know if her BF's exwife had a problem with his friendship with his then not-as-yet-girlfriend-just-lifelong-friends? Did he "cheat" on his then-wife? Did he "cheat" on his exGF when they were dating? Has her BF behaved or spoken in a way that makes her feel insecure in the relationship or causes her to fear that he might cheat on her? And, finally: Have they previously agreed to exclusivity? If they haven't discussed and agreed to exclusivity then he wouldn't necessarily be cheating on her if he did "get up close and personal" with his exGF. This could be another reason for her feeling insecure.

@6: Sportlandia, I'm constantly surprised that advancing age doesn't necessarily make people wiser or smarter, or better communicators or more ethical, or less in the thrall of their libidos than they were when they were, say 30. Although in general, I agree with the rest of your comment with the minor change of "Can my boyfriend of 8 months be around a woman without fucking her?" to "Can my boyfriend be around a woman he used to date without fucking her?" Actually, it seems to me that the bottom-line question this woman and others needs to ask is"Can my boyfriend be around a woman without fucking her?"
And if they truly believe the answer to be "no," then they should do both parties a favor and break up.
I have two such lifelong friends and have done the bucket list trip planned well in advance with one of them and it was even just the two of us together for a week of it due to other friends having obligations. It would have been a total deal breaker had anyone tried to interfere with that trip. And it's silly to worry about the ex when there will be no shortage of other people LW's boyfriend can hook up with on the trip AND not have follow him home.

Don't know if the geography is favorable, but there is time before the trip, maybe letter writer might invite the ex to some social function she will be at with her boyfriend, or have him do so? Meeting the people who have been involved in your significant other's life forever is just good practice anyway.

LW should definitely NOT try and get invited on this trip. A significant other thrown onto a group of friends on a trip just makes everyone resent you.
It sounds like, given how long LWs partners' marriage was and the fact the, he and Bestie had been so for so long, their romance provided him with some much needed comfort at the time when he maybe needed a compassionate rebound with someone whom he was already comfortable, but didn't want to enter the dating scene again. When he was ready to date "for real" again he met LW. Nothing to worry about. LW should spend time getting to know bestie because she can feel reassured about bestie's intentions if she gets a sense of them from bestie directly. And also bestie isn't going anywhere. What Dan said is likely true about bestie being partners confidant.
Or maybe he was married for 2.5 years and she forgot the decimal point. That would make a lot more sense.

There was one female friend that my boyfriend had who made me suspicious. She wouldn't talk to me or look at me, would sit in between me and him when we were all out together, etc. I don't think I was wrong to tell him to cool it with her (and her reaction to that proved me right). Whereas I'm delighted he has other close female friends. So sometimes it's not just irrational jealousy.
Ms Cute - I'll give it nine out of ten - shades of Patrick Redfern's response to Poirot's solution in Peter Ustinov's Evil Under the Sun; he deducted one mark for total absence of proof. I'll deduct a mark for Mr Savage's not telling LW to dump the "deal-breaker"-pushing friends.
That headline was a bit misleading. I was all set to agree to telling the friend to fuck off (I am in general a fan of this at the first sign of drama) but how do you tell someone to fuck off if you have never met them? The most she would be doing is telling her bf to fuck off. Solid advice to the letter writer, who should have a bit more reason to distrust her bf than just her friends in her ear. If he hasn't given her any reason, sit back and let him enjoy this trip that he won't get to go on again. Dan is right, missed opportunities lead to resentment, even when they happen for far better reasons than one partner's insecurity.
beesting@12 ~ "...It sounds like, given how long LWs partners' marriage was and the fact the, he and Bestie had been so for so long, their romance provided him with some much needed comfort at the time when he maybe needed a compassionate rebound with someone whom he was already comfortable, but didn't want to enter the dating scene again. When he was ready to date "for real" again he met LW..."
That was going to be my response! He tried it and it didn't "work" so he moved on. Rebound relationships usually don't endure because they are fulfilling a temporary need for reaffirmation of desirability combined with "finally, I get to sow some wild oats!" How you both handle this will define your relationship forever. Will you be the suspicious, non-trusting partner? Will he be the fuck-around-on-the-side-at -the-first-opportunity partner? Tune in next month for the answer! Same bat-time, same bat-channel.
I would've worded it more like this:

"Look, WWDD, if you and your boyfriend are going stay together — for five more months or fifty more years — you need to have a little trust, for fuck's sake."
The only possible objection I could think of would be if the boyfriend cheated on his wife with the friend. In that case, yeah, I'd be concerned. Otherwise, I'd figure their romance was a sorta "well, I'm single now, I should probably date someone... um, hey friend, wanna try dating... welp, that didn't work well - let's go back to being friends" -type situation and I wouldn't be bothered.
"... I didn't tell [now-Hubby] him not to go, WWDD. Indeed, I encouraged him to go. And I think that's part of the reason why he's still here." Dan, you sly devil! Well played, sir.
Obv he goes on the trip and she is 100% good about it. No other option, your friends are dumb LW. That said, the way to not make it the high stakes gamble people apparently commonly risk their relationships on according to the comments is for the LW and the ex to hang out w the bf together - she's a close friend, this can't be hard to do. The threat feeling apparently goes away when you get to know the person. I routinely stay w male friends and exes when their gfs/wives are away and it's 100% fine when everyone knows everyone else is cool and good with boundaries. The only possible downside is that it's highly likely that your GF and female friend will get along better than you do w your female friend and you'll lose every possible argument/vote on what to eat/watch/do when you're hanging out together. You get ahead of things by asking your partner if she's the jealous type or just assuming there's going to be some potential for jealousy if they are, like Dan's ex, potentially sharing a tent w an ex or something.
@13 Correct. But that's not this situation at all, so it's fine.
@6 Most guys can do that in their teens.
Has there been some serious editing here? "You're afraid you're going to lose him if he goes on this trip with his ex" -- she never implied that. "[Y]ou're definitely going to lose him if you force him to choose between you and this bucket-list trip and/or his lifelong friend" -- she never implied that either. In fact, she said, "I want to give him the benefit of the doubt here. He was at least open enough to tell me.... I really don't want to judge him before the trip even happens. It's one of those things where deposits would be lost, and it's on his bucket list." It sounds like she's fine with it, and the only issue is that certain friends are telling her she shouldn't be fine with it, so she's doubting her instincts. Fortunately, she chose wisely -- she chose to ask the one advice columnist who's pretty much guaranteed to confirm her instincts that she should give him her blessing to go on the trip. Not sure why he complicated matters by citing nonexistent "nervousness over his potential cheating" -- which, again, she never implied.

Is it too late for WWDD to come along on the trip, too? Sounds like a really fun vacation.
Mike @3: I'm bi, but most of my exes are the opposite sex and I'm still friends or friendly with most of them. Including one who stays with me whenever he's in town and is in my will.

Sublime @5: Wife could have been his high school sweetheart. Married at 18 or 20, so he's now in his late 40s. Point stands that these are not horny teenagers.

Elm @13: No, 25 years makes perfect sense to me. Sublime's take makes sense: childhood friends, each (?) marries someone else and they stay friends, both find themselves single in their 40s and think, hey, we've always liked each other, perhaps we should be more than friends. Then they try it and realise that no, they're better as friends.
My, what a lot of assumption. WWDD's letter and question is really quite reasonable. Her boyfriend is going on a trip, and she has some misgivings about the situation. She asks what the right thing to do is. The headline makes it seem like something else altogether as does Dan's answer.

WWDD never said she was blaming the ex-girlfriend for existing or for going on the trip. WWDD never hinted that she wanted to tell the best friend to fuck off. I came here ready with a comment about how women get blamed for infidelity when it's the men who are engaging in it, but when I reread, I see that's not in the letter.

Then Dan's answer about what a bad idea ultimatums are and how she's definitely going to lose him if she shows any jealousy. That's all true, but the only thing in her letter that hints at jealousy is where she says she wants to give him the benefit of the doubt and doesn't want to judge him before the trip even happens. The letter is actually quite mild.

BiDan has a good answer. See about going along on the trip. It sounds like fun, and it would be a way to get to know BF's friends including his best friend of many years.
@25 nah on going along w the trip. Throws off the old friends vibe. Awkward to break into a group she apparently hasn't much been in (out she'd trust the other people on it even if she hadn't met the ex), it's not what he wants bc he would have invited her, and unless she gets lucky it's not likely going to be much fun for anyone if she third wheels the entire group. Especially if she's just there to eagle-eye the ex.
I agree that going on the trip is a bad idea. Trips are way more fun with groups of people with an established dynamic. Trying to fit a new squeeze into an established friend set always has a few rough patches--don't make them happen on a trip he's been wanting to do forever. When everyone's back, get to know his friends through the usual dinner parties, bars, whatever your group does, and then go on some other trip together sometime. But this one you should let them do as-is.
Yes, agreed with what no @26 and ciods @27 say about the LW going on the trip.
Also wanted to address the mention of "spring break" -- it's possible that one of the group is a professor/teacher, rather than student.

I'll back down from my suggestion of inviting herself on the trip, mainly because I'm assuming that if it were logistically possible she'd have already thought of it, so it must not be for whatever reason.
This is just pure conjecture, but I wonder if the LW and the BF are different ages? As others have pointed out, by the math he's in his 40s or 50s. And LW referred to the vacation as being "spring break", which makes her sound young and/or as if one or both of them are in academia. Perhaps he is a professor and she is a college student or in post-grad? This would explain the use of spring break and why she sounds younger than the BF. While in my 20s I definitely had female friends who would have advocated for me to dump a BF in this situation. Now in my 30s, especially my late 30s, none of my female friends would say that. By now, we've all had plenty of ex's. You understand having an ex as a good friend or even considering them family when you are a bit older.
It's always weird when a new person joins an established friend group. It's particularly weird when that new person is the new love interest of one of the members of the group, because then the group member acts differently than before. It can be irritating. This is a trip that has been planned for a while and I don't think WWDD should invite herself along.
But she can arrange to meet more of her boyfriend's friends, especially this woman, and spend time with them and hopefully become friendly with them. That would probably help dispel the nervousness she feels.

I don't think her worries are all that crazy: he has not only known this woman most of his life, but they dated almost twice as long as she has been dating her boyfriend and this woman was her immediate predecessor. It really depends on why they broke up and how secure the lw is in her relationship with her boyfriend. It sounds like her friends don't believe that exes can ever be friends or that men can ever be trusted (or maybe they think that women can never be trusted to not be predatory man-stealers or something like that).

The lw says that her bf and the other woman dated "a year-and-a-half in total after he ended a marriage of 25 years." The "in total" suggests to me that after his long marriage ended, he started relying on an old family friend for comfort and they sort of half-heartedly segued into a dating relationship that eventually fizzled out and reverted to familiar old friendship. That scenario would also account for the fact that less than a year after breaking up, the two are still planning on going on a trip with a group of friends. It doesn't seem likely that the ex-gf has been plotting to reseduce the lw's boyfriend on this trip.

I don't know why so many people are hung up on "spring break." A lot of people have jobs in academia from kindergarten through university. It's highly likely that at least one member of the friend group has to plan his or her vacations around the school calendar. They could also be including their children, who are still tied to the school calendar. There's nothing in the letter to suggest a massive age disparity between the lw and her bf.
@22 plz read por favor
@23 I'd argue that's more contemptible. Like, LW is writing Dan for permission to tell her BF that she doesn't like the idea of him traveling with his ex ... and then have nothing to say about if he goes on the trip or not? That's some heavy-ass guilt tripping, a great way to hang a black cloud over a trip. If it's a weekend trip to see some friends, it's a lame enough guilt trip but the stakes are pretty low. If it's the trip you've spent a lifetime planning? Would you be OK with one of your partners throwing shade on you like that?
Sporty @23: Of course you would.
I definitely agree with everyone saying that she should not try to go on the trip and the point about a long planned trip not being the best to suddenly bring in a new person. I would add that it is also a useful excersise in a relationship to tamp down the FOMO or the "is everyone hanging out without me?!" And be happy that one's partner is pursuing and interesting life and will return with good stories.
If anyone were in doubt, Sporty's comment @33 seems conclusive evidence that no woman can ever do anything right.

LW has no problem with this trip. Some of her friends are saying, "Wait, what? Your boyfriend is going on a trip WITH HIS EX and you're okay with this? Doesn't that seem weird?" And she thinks, "Well, it didn't, but maybe I should get another opinion." And she writes to someone sex-positive to confirm that her friends are off base and she indeed, in all probability, has nothing to worry about (though oddly using language that seems designed to raise suspicions she wasn't even entertaining).

And you've somehow managed to read "heavy-ass guilt tripping" and "throwing shade" into her probable being reassured enough to say nothing to the boyfriend. How "contemptible."

Seriously, dude, get help.
To answer your question, I would absolutely be okay with a partner voicing concerns about my friendship with, say, the ex I spoke about @24. It is, in fact, unusual for exes to be so close, and it wouldn't be out of line for a new partner to find it odd enough to ask about. I would reassure them that the romantic side of the relationship was long over and they had nothing to worry about. If they didn't accept that, there would be problems. But simply asking wouldn't be a red flag.
Bi, I think Sporty is imagining a situation where someone says, “I really don’t like the idea of you going on this trip. Buuuut...the decision is yours, I guess,” with an ominous and meaningful look. As in, you better not go on this fuckin trip.

If that’s what he’s describing, I agree. Passive-aggressive guilt-tripping sucks. I would rather hear, “I don’t want you to go on this trip,” full stop, and then you fight about it and everyone knows where everyone else stands. Or it’s, “Hey, enjoy your trip. See you when you get back!”
Late @38: My comment was phrased defensively. But looking at it more sympathetically, my point stands. If Sportlandia's experiences have led him to presume that someone having a slight niggle about whether it's appropriate to go on a trip with someone he used to have sex with is "contemptible," and would constitute "heavy-ass guilt tripping" and "throwing shade," then as Carolyn Hax would say, wow. Those experiences must have been some seriously abusive doozies to lead him to read that into such an innocent question. I saw no hint of passive aggression or of guilt tripping; the only place that could have come from is his own mind making such assumptions because that's what his own past relationships were like. I stand by my suggestion that he get help, because that sort of reaction is not healthy.
I love the words, " I want to give him the benefit of the doubt here.." This from a woman he's been with for eight months. And if she is a woman in her forties, why has she still got friends who behave like college kids.
Smile and say bon voyage, any more words and this man will smell the cell walls getting built around him and he'll split.
@37 Is it unusual? Did no one else date the girl next door? Doesn't everyone know at least one person who is best friends w/ their ex? Don't most people have childhood friends still in their life? It doesn't seem odd to me at all, and if anything far more of a reason to trust than otherwise.
This guy has successfully not fucked this woman for what, 38 out of 40 years they've known each other? Those are good odds.
Boyfriend has known the old squeeze for decades and even dated her for a year & a half. I'll add my voice to the chorus that says the deadline for anything serious happening has come and gone. That doesn't rule out a little friendly slap & tickle for old times' sake on the vacation, of course. But he could do that with any hottie on the beach. Unless they know something you don't know, your "friends" are giving you bad advice. File that bit of knowledge away for future reference...these people are no better a source of reliable advice than Kelleyanne Conway or any random Kardashian.
The LW's and her friends' expectation--that everything will be perfect, will be exactly as desired--is disastrous. Because what if your partner counts on 'perfect', too--and 'his' perfect isn't your perfect? That kind of 'just-what-I-expect-or-it's-a-dealbreaker' expectation sets you up for one of two things: failure or self-deception.
What sticks out here for me is the LW's lack of care for her bf. He's going on a trip which has been long planned and he's had it on his bucket list and all the LW is thinking about is herself.
Maybe she could put her mind to hoping he has a great time and stays safe.
@39 like I said, I've literally lived through this. I find your characterization to be... unlikely. If LW had no problem with the trip, how did we end up here? Her girlfriends found out the ex would be with them by magic? And we're consulting Dan for a second-opinion on something that (per your words) the LW doesn't really care about? That doesn't jibe with reality. But then again, reality has never been your strong suit, carry on.
@46 ~ Sporty, you were doing fine right up until you just had to throw that last little insult in there. Try to make your point without being a dick. It’s debate club rule #1.
Sporty @46: You find my characterisation to be... unlikely because you assume the absolute worst about any woman in every letter that runs in SL, regardless of whom it's written by. You always twist it so that she's the bad guy, even with evidence to the contrary ("I'm inclined to give him the benefit of the doubt"). You're unable to picture a reality where a 40-something woman, a, has friends?, b, is discussing her plans for "spring break" with her friends as including the fact that she's free because Boyfriend is off with some old friends, including one who's an ex, but that's fine, right? Funny how I can so easily picture that reality because this happens with female friends. (And who said these friends were female? Maybe it's a MALE friend who's saying this guy won't be able to be around his ex without accidentally fucking her, eh?)

Donny @47: It's ok, I've grown bored of constantly pointing out Sporty's misogyny. All but two people on the board can see it clear as day; my drawing continued attention to it isn't really helping. As Late @38 says, "I think Sporty is imagining a situation." Yes, I think so too; the question is why is he imagining this particular situation? Because a similar thing happened to him, so therefore this one must be identical? Why must it be identical when there are different people involved? Questions to hash out with a therapist.

As an offer of kindness to the rest of the SLOGgers, I'll offer a truce. Sporty, you don't reply to my comments and I won't reply to yours; your misogyny can speak for itself. Deal?
I'm not at all familiar with the discourse on PUA message boards or among MRA. Inasfar as I can guess what it is, it would be anathema to me, so I don't inquire too closely. That proviso out the way, I would say that Sportlandia responds to situations very much as himself, as an individual, yes, with his own priors and assumptions, but one who's trying to be fair-minded. Further, I don't see anything iniquitous at all in wanting to reply as a representative or spokesperson of a group, especially if that group e.g. single straight men with e.g. relatively vanilla tastes are proportionally underrepresented in a certain context. Of course, sometimes (in my view) Sportlandia will state a certain group / interest-group perspective fairly and normatively, and sometimes not--but which and when really aren't the issue; honesty and the desire to voice one's truth matters more.

This isn't about which of two commenters is more often right, again to my mind. I'd think Bi right 90% of the time, and a clarion voice for compassion and thoughtfulness in sexual ethics.
Thank you for your kind words, Harriet @49. I guess I like to hope that straight men as a group are not represented by a subset of straight men who don't consider women human beings. Certainly, few of the straight men I know fit this description.
Heterosexuality seems so fraught. Most of my and my husband's friends are men we used to date or met while hooking up.
@47 that nicety came and went a looong time ago.

@48 if she were inclined to give him benefit of the doubt, she would have given him the benefit of the doubt. The very act of collecting opinions of friends, then writing to a nationally syndicated columnist is the literal act of not giving benefit of the doubt. She'll give the benefit of the doubt - only if others have given her a sense of certainty. Hmmm.

No truce. You've been going out of your way to drag me for years. If you want to duck out, I can't stop you, but asking for special consideration now is the height of arrogance.
One of my really good friends had a situation like this. A girl he started dating had a guy coming into town to visit her for a week that was planned before she met my friend. Out of all of his friends, I was the only one who told him to cut her a break and trust she wanted to be dating him. He listened to me, and they've been together 9 years. They still credit me for my advice in keeping them together.

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