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“My Boyfriend Still Financially Supports His Ex-Girlfriend!”

I’ve been dating a guy for nine months. We’re in our mid-twenties and started dating right after he had broken off a LDR with “Kerry,” an unemployed, 30-year-old musician with delusions of a future rock goddess career. While she is probably talented, she refuses to find gigs/jobs to support herself, and my boyfriend, during their relationship, ended up supporting her entirely from paying her rent and internet to buying her food, furniture, necessities and toys (iPad, guitar accoutrement, etc.). They dated for about two years, and yet she never intended to move in with him or take the relationship any further while putting my boyfriend into substantial financial debt for her upkeep.

He was so miserable that he has even admitted to having flings during their “open” relationship to keep from breaking it off with her; flings which I have found evidence were not simply mutual, but financially compensated. How have I found this out? I checked his phone and snooped his email, which is where I found irrefutable proof as to Henry’s continued emotional/financial support of Kerry. However, every time that I ask him if he’s gotten rid of her joint credit cards and changed his passwords on his internet accounts, he states, most definitively, that he has. Boldfaced lies every time.

Henry is a sweet, caring individual. He is sensitive and very good to me — except when it comes to honesty on this particular issue. Part of me excuses his continued support because I know he’s doing it out of a sense of duty and because he cares for her — not necessarily in a romantic capacity, but as a friend or family. I really love everything else about Henry, but I’m afraid to find an apartment with him if this is going to continue, and how are we supposed to have a future life and children together if he continues to feel like he has an obligation to her? I know he has been faithful in the physical sense, but I can’t help but feel cheated on emotionally. How do I confront Henry about this matter and make sure that he follows through? And do you think I should even bother, or should I cut my losses and run? — Oversize Baggage Charges

How do you confront Harry? It seems you already have confronted Harry, haven’t you? You’ve asked him numerous times if he’s gotten rid of his joint credit cards with Kerry and you say he boldface lies to you each time you broach the topic. Your real problem here isn’t that he’s still financially supporting an ex – though that’s definitely problematic and weird — it’s that you can’t trust the guy and you have poor communication. You’ve resorted to snooping through his phone and emails to gather incriminating evidence. You don’t believe things he tells you. At this point, I’m not sure what you’d lose is you just flat-out told him you’ve been invading his privacy and demand to know why he keeps financially supporting an ex he broke up with nearly a year ago.

True, confronting him in that way almost guarantees some issues in your own relationships, but, honey, you’ve already got major issues. You’ve said yourself there’s no future between the two of you as things stand now. How can you move in with him or think about having a family when you don’t trust him? When you know him to be driving himself into financial ruin by paying some ex’s rent? The only chance you have at any kind of real future with him — and that’s a small chance at this point — is to come right out and confront him with the information you have and ask him why he continues to support his ex and lie to you about it. The “how” in this scenario is to come right out and do it. Don’t pussyfoot around the topic. Just come right out and confess that you’ve done some snooping — you aren’t proud of it — but you found this information that leads you to believe he’s been lying to you and you want to know why. And then tell him that you feel betrayed — emotionally cheated on — and that his loyalty and obligation should be to you now, not some woman from his past.

As for his reaction, you’ll have to wait and see. He’ll probably be angry. He may be embarrassed. He may lie some more. Be prepared for the worst. Decide for yourself that there’s only one way this relationship can possibly continue and that’s if your boyfriend can convince you to trust him again (and vice versa). That won’t happen overnight and it can only begin with a long overdue conversation in which you lay all your cards on the table. If you can’t handle that first step, you might as well MOA now, because there’s no other way this relationship will survive and move past go.

*If you have a relationship/dating question I can help answer, send me your letters at wendy@dearwendy.com and be sure to follow me on Twitter.


Comments on this entry are closed.

avatar silver_dragon_girl August 2, 2011, 3:04 pm

I’m gonna go with GET OUT GET OUT NOW.

Wendy’s advice is very calm and well-thought out, and there is definitely a lot of merit to that approach, but I strongly suspect that this guy is not going to change for quite a while.

avatar justpeachy August 2, 2011, 3:11 pm

Oh HELL no! I get supporting your live in girlfriend. I don’t get supporting your long distance girlfriend. I REALLY don’t get supporting your long distance ex-girlfriend.

You’ve really been painted into a corner on this one. Your best bet at this point is to come out swinging, guns a blazing, and let him know you know everything and it ain’t gonna fly. Stand your ground, let him unleash fury for the fact that you snooped, and let it bounce off of you.

Only after everything has been aired do you have any chance that this relationship can be saved. Without a clean slate, it’s only a matter of time until everything implodes.

Or, just MOA since this guy makes no sense to me.

avatar LTC039 August 2, 2011, 3:15 pm

Yeah, no, I would NOT be ok with this if this were my boyfriend. I second the GET OUT NOW. Why do you want to put up with a guy that has allowed another person to drive him into debt? It sounds like he doesn’t have much a backbone & his priorites are way off. He is putting his ex’s feelings over yours, plain & simple. If he was putting you first, he would tell his ex to get bent & figure shit out on her own. This girl was obviously using him for his money…That’s his deal if he put up w/ it while he was w/ her, but he’s with you now & he needs to respect your feelings. He’s lying to you over & over. If you want to talk to him, follow Wendy’s advice, however, IMO you shouldn’t put up with that.

avatar Maracuya August 2, 2011, 3:17 pm

“He was so miserable that he has even admitted to having flings during their “open” relationship to keep from breaking it off with her…which I have found evidence were not simply mutual, but financially compensated.”

Wait, am I reading this the right way?

avatar justpeachy August 2, 2011, 3:19 pm

Wait, did she mean hookers? How did I miss that?!?

Dear Wendy Wendy August 2, 2011, 3:35 pm

I think it was awkwardly-worded and what she meant was that the boyfriend also financed those flings, too, with gifts and the like. But I could be wrong. Maybe these ladies really were hookers, in which case, gross.

avatar justpeachy August 2, 2011, 4:28 pm

I just want an update to clarify the involvement of hookers in this story.

avatar LW August 2, 2011, 5:22 pm

No, I was being eloquent. I meant either a one/couple time affairs (for the most part– except for one that he lent money to and just received part of it back) with girls who charged a fee for their company through dating sites, craigslist, and escort services. I didn’t even know they had escort services in this state; I was/am pretty sure it was/is illegal.

avatar SweetChild August 2, 2011, 9:42 pm

That still doesn’t make it much easier to figure out. Sounds like hookers…

avatar ele4phant August 2, 2011, 11:00 pm

This still isn’t clear to me what you mean.

avatar ReginaRey August 3, 2011, 8:20 am

Wait Wait Wait. Your boyfriend paid for escort services WHILE he was financially supporting his lazy ex-girlfriend, who he is still supporting while he is dating YOU, and you haven’t left him yet?! Girl, your boyfriend is not the only one without a backbone.

avatar Maracuya August 3, 2011, 9:52 am

The phrase ‘escort service’ is synonymous with prostitution to me.

You sound like a lovely girl. I think you can do better than this guy.

Budj Budjer August 3, 2011, 10:08 am

Yes…I never have, but I had always assumed that if I did order an escort service it’s like paying for having a “social event date service” for the night out and the fine print is if you aren’t completely revolting you get laid at the end…or even if you are you can tip enough and still get laid.

avatar VioletLover August 5, 2011, 1:35 am

Er…I know that some are legit, but isn’t ‘escort service’ a common euphemism for hookers? Especially craigslist, that site can be way sketchy. LW, I hope you talk to your OB-GYN andget tested…just in case.

avatar beans629 August 2, 2011, 3:46 pm

Yeah, that one totally threw me for a loop. I just thought I read it incorrectly.

Hmm, Let’s see he’s either into hookers or being a sugar daddy. I can’t see the upside of either of those choices from his past. I don’t think this bodes well for LW and she should run so fast from him that all he sees is a dust cloud.

avatar LTC039 August 2, 2011, 3:56 pm

My first thought was hookers, but Wendy’s suggestion could be possible.

avatar Maracuya August 2, 2011, 4:00 pm

I actually at first thought she meant sugar daddying, but then I read it again and it’s a little ambiguous. Also, why were there quotes around open? Because …it wasn’t?

I just wonder, does he treat you as well giving-wise too, LW? And I don’t mean just money. I mean generosity. He sounds …bleh.

avatar Valerie August 2, 2011, 4:46 pm

Yeah this is very strangely worded. The way I read it was that Harry had flings, but his “open relationship” with Kerry wasn’t mutual, so he made it up to Kerry by buying her things. Could that be it??

avatar Blitzen August 2, 2011, 9:52 pm

That’s what I thought. *confused*

Skyblossom Skyblossom August 2, 2011, 7:48 pm

I took it to mean he was compensated by the women and he did that to make money for the exgirlfriend.

JK JK August 2, 2011, 8:12 pm

That’s how I understood it, too.

avatar artsygirl August 2, 2011, 8:49 pm


avatar kerrycontrary August 2, 2011, 3:22 pm

Ok, I’m going to be harsh: Why do you even want to fix this problem and stay with this guy. If I found out that my boyfriend was lying to my face like that I would’ve left a long time ago. Your hormones are clearly clouding your brains and decision making skills in this situation. Your boyfriend is a liar and a coward. He couldn’t even properly break up with this girl who was taking advantage of him. Instead he sort of cheated on her, which is obviously the most mature decision in that situation. Plus, everything you know about this horrible ex is from your boyfriend’s point of view. There are two sides to every story so I would like to hear hers. And if your boyfriend isn’t great on honesty in this situation, he’s not great on honesty period. Oh, and yes, your boyfriend IS committing emotional infidelity.

avatar BigRedYouSay? August 2, 2011, 7:22 pm

Oh yeah. I’m impressed with Wendy’s compassionate and diplomatic advice, but honestly? My reaction was “Head? Meet desk”

MaterialsGirl Elizabeth August 2, 2011, 3:27 pm

Here’s the thing: even if this all magically went away and he apologized, cut ties with her, got checked for STD’s, etc… he still can lie to you ‘boldfaced.’ Do you think you’ll be able to ever trust him again? Most people would be told to go to counseling after something like this, but that would be in a situation where the two people have been together for a significant amount of time. I dunno man, I would say “sorry, i don’t trust you, here’s why, I’m out.”
If you guys do stick together after the previously mentioned miracles happening: have him run a full credit report before moving in together. I can only imagine what she’s done to his credit. You don’t want to find out hes 100k in the hole because of her.

MaterialsGirl Elizabeth August 2, 2011, 3:28 pm

happen* not happening..doh!!

avatar Maracuya August 2, 2011, 3:30 pm

Oh, yeah, I forgot to comment on the actual letter as I was so flabbergasted that you’d stay with a guy who paid for good-time girls while dating his messed-up girlfriend. Let’s look at the facts: you guys are in your mid-twenties, and yet this guy is getting in debt for an ex-girlfriend who is 30 and can’t even manage to pay her rent. Then he’s lying to you about it to your face, when asked repeatedly. Also, why were there quotes in “open”…was it not open? Please tell me it really was, because the alternative is depressing.

Why would it be so difficult to be truthful? “Yeah, I’m paying her rent but I’ve drafted a formal loan agreement.” Because he feels guilty about it because he knows he shouldn’t be? There’s just too much weird, even if he’s noble in his intentions he sounds like a doormat. If my BEST friend was in real extenuating circumstances trouble, I would lend her rent money for a month or two. If it was someone who can’t be bothered to find work…seriously, what would your opinion of me be? He’s been lying to you since your relationship began. Rant over.

Budj Budjer August 2, 2011, 3:41 pm

Sounds like she stopped having sex with him and told him he could have sex with other people as long as he kept paying her rent…LW, maybe he got sick of paying for the side sex? Regardless…move on – this guys either a user or a wanker.

cmary CMF August 2, 2011, 3:41 pm

Oy. Do you actually think this guy is THE BEST guy out there for you? Be honest. If he’s lied about it before and you know that and you stuck around anyway, what’s to stop him from lying about it again? I don’t see what confronting him would matter. I say move on. And! if it was an “open” relationship, why was he sucker enough to support her?

“He is sensitive and very good to me — except when it comes to honesty on this particular issue.” Oh, is that all?

My head hurts.

avatar Joanna August 2, 2011, 3:42 pm

How do you know she’s an ex-girlfriend? Or is that just a story he tells you, cause you’re another “fling”?

avatar Kristin August 2, 2011, 4:35 pm

My thoughts exactly!

avatar MiMi August 2, 2011, 4:48 pm

yeah, I don’t think you actually have a boyfriend, LW.

avatar BGD August 3, 2011, 3:09 pm

I agree!!! And is it possible he has a child with her and that is the real reason he is still paying?

avatar oldie August 2, 2011, 3:47 pm

MOA. This relationship is not fixable. The only logical explanations for his behavior is that he is still having a relationship with this woman, that she is blackmailing him over some serious crime he committed, that he honestly believes she’ll kill herself or him or you or a member ofhis familly if he stops the payments, or that he has significant mental issues and sees her as his Mommy. I don’t think I missed anything. If this were simply a case of altruism that he can’t afford, would he lie like this about it?

avatar oldie August 2, 2011, 3:48 pm

I guess the idiot could think he is going to be a rich man off of half her concert revenue when she inevitably becomes the one in a million rocker to get a start after 30 and make it huge.

avatar SweetChild August 2, 2011, 9:46 pm

Yeah what’s up with that? How many people make it big in any form of music after 30? NOT FRIGGING MANY AND DEFINITELY NOT ROCKERS.

avatar Jena August 3, 2011, 10:21 am

Actually most dudes in bands are pushing 30 when their band finally “makes it” — they’ve probably been working 10 years to get there, but still.

Budj Budjer August 3, 2011, 10:25 am

agreed…takes a while to build up that momentum in the rock industry. Pop stars, however, are a whole nother ball of wax…

avatar AnitaBath August 2, 2011, 3:52 pm

The middle paragraph just confused me and kind of threw me for a loop. I think it shows that the LW has her own problems and insecurities, and when added to the weird relationship Henry has with his ex it seems to be a recipe for disaster.

avatar Bethany August 2, 2011, 4:12 pm

This whole situation is so F’d up it’s not even funny. There is NOTHING that’s presented in this letter that would give me even the slightest glimmer of hope that they could or should work this out. There is nothing here that says “good relationship” to me.

MOA, and FAST!

avatar demoiselle August 2, 2011, 4:17 pm

The guy’s story does not make sense. He’s probably lying about his past relationship in one way or another. If he was “over” his ex, and the relationship wasn’t good, and there were no other ties, then he wouldn’t be doing this. Maybe his ex isn’t as awful as he says. And maybe one of these alternatives is true:

1. He’s still in a relationship with her.
2. He has a child with her who he hasn’t told you about.
3. He has a drug problem and she’s his connection. Or she’s blackmailing him.
4. He believes she’s going to make it and he wants to bask in her glory if it happens.

Anyway, it doesn’t really matter. His behavior doesn’t make sense. His story doesn’t make sense. He’s a baldfaced liar. And most likely, he is the bad guy, not his ex, and he’s telling tales to deflect attention from himself and onto his ex.

avatar Marjoralynnia August 2, 2011, 4:32 pm

I disagree. I think it’s entirely possible that he just has delusions of his own importance. Perhaps he has developed a false sense of responsibility, and has convinced himself (or his ex has convinced him; probably both) that he’s the only thing that’s saving her from life on the streets, trading blowjobs for food. (I’ve known people with this mentality who have trapped themselves in destructive entanglements with friends or exes).

That being said, he’s still a liar, and you’re right, if he was truly, 100% over her, he would realize that she’s an adult, and her wellbeing is up to her, not to him.

caitie_didnt caitie_didn't August 2, 2011, 4:29 pm

Um, what? This letter confuses the crap out of me. Either BF is still with the ex or he’s a spineless moron.

avatar Eljay August 2, 2011, 4:30 pm

I’ve always said “When someone shows you who they really are, believe them!” This guy is a coward, has no self worth, does not value you or your relationship and is so easily led and influenced by others that he will never be able to think for himself. Not someone you want in a friend, a bf, a lover, and most definitely not a life partner. Until he grows up, grows a spine and starts thinking for himself, you’d be better off without him. MOA honey, there’s better men out there than this dudeface.

avatar SaraiLuv August 2, 2011, 4:33 pm

Please, oh please give us an update on this. I have to see what his response was if you tell him you know everything. I hope you find enough nerve to let him know how disrespected you feel and how unacceptable it is for him to lie to you like that.

avatar Natasia Rose August 2, 2011, 4:43 pm

Maybe he is in a long distance relationship with his “ex” and that’s the real secret! Dun dun duuuun.

Either way you can’t trust him. MOA.

avatar Greebo August 2, 2011, 4:44 pm

Middle paragraph: wait, what? He admitted to flings, and you know this by snooping? Or he admitted to flings (what is a mutually compensated fling, exactly?) during an “open” relationship (why the quotes? And if it’s an open or casual relationship, are they flings or just other people he dated?), and for whatever reason you snipped and found proof he’s lied about severing financial ties to her? I don’t understand.

Regardless, he’s lied. You know he’s lied. He isn’t changing anything despite knowing that you know he’s a liar. You can do better than this. Would you really want to spend 1, 5, 10 or more years with a guy who constantly left you wondering whether he could prove whatever he told you? Worse, imagine financial ties to this guy! Some relationships can’t be fixed. Your instinct says this is one of them. Trust that.

You can find better than this guy.

avatar Greebo August 2, 2011, 7:38 pm

*snooped, not snipped

landygirl Landygirl August 2, 2011, 4:55 pm

LW, I’m not sure who is a bigger masochist here, you or your boyfriend. 9 months into a relationship you’re spying on this guy because you don’t trust him. That is not a good thing. MOA before you invest any more time with this guy.

Maybe Wendy should start some new features called “You May Be A Masochist If:”
and “Updates, Major Details I Forgot To Mention In My Original Letter Which Totally Changes The Advice”.

avatar Kate August 2, 2011, 4:57 pm

“Updates, Major Details I Forgot To Mention In My Original Letter Which Totally Changes The Advice”

I vote for this one!

avatar melikeycheesecake August 2, 2011, 5:13 pm

I’ll second that motion.