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#1263: “I apologized and it made everything weirder. What’s really going on?”

By
April 7, 2020
boundaries, BREAKING UP, bygones, COMMUNICATION, Geek Social Fallacies, how to say no, Overthinking It, Reader Questions, Relationships, Uncategorized

Dear Captain,

I’ve looked in the archives for something like this, but I couldn’t find anything. What do you do when you apologize and it seems to upset someone even more?

I (she/her) have an ex (he/him), and we have recently reconnected after a breakup and period of no contact and are trying to be friends. He was the one who ended the relationship, if that helps, and I was the person who asked for space, and recently reached out. We broke up mostly because he wasn’t the best communicator, and when I brought it up he said it was easier to break up. (He is a Geek Social Fallacies carrier)

I live in an area under shelter-in-place, and after that started he started texting and messaging more frequently, and then occasional phone calls. I wasn’t sure I wanted this much contact, but was feeling a little lonely with the SIP, and figured he was as well, we could support each other a bit. I have a wide ranging circle of friends that I have been virtually in contact with, I wasn’t focusing on him.

Anyway, we were talking about what we’d been doing since the SIP began, and I mentioned I’d been working on my writing, and he expressed interest in it, and I asked if he’d be willing to give me some feedback. This wasn’t unusual, it had been something he’d done for me when we’d been together. So I emailed it to him, he emailed some feedback (which was good feedback!), and I got caught up thinking about it and how the writing worked with his feedback, and I guess I hadn’t responded or said thank you, quickly enough? Because a few hours after receiving it he texted to ask if I’d gotten it. And I realized I hadn’t acknowledged it, apologized and thanked him.

And then a few days later I asked if he would read over an article I’m working on, and he said yes. He read it and sent me feedback a day or so later, but I was caught up in work when the email arrived (SIP and working virtually means I get SO MUCH MORE EMAIL than usual, and I got a lot before!), and I just didn’t get a chance to respond. Partially because I felt that he deserved more than a, “thanks, got it” email.

But the next morning beforeI got a chance to do this I got a text saying it was “weird,” I hadn’t acknowledged his messages. I emailed back, apologized, and thanked him. He then asked if we could have a phone conversation, which we did that evening.

Prior to our phone conversation, I realized he was probably feeling unappreciated, and made a point of acknowledging that when we talked, and said that he was also probably trying to show that he cared for me by doing me a favor, and that was really nice, and when I didn’t respond quickly enough he felt ignored or rejected or vulnerable.

And by saying that, he seemed to get really annoyed. Claimed I must be feeling resentment for our breakup, and that it wasn’t any “psychobabble” about feeling vulnerable or rejected, he’s obligated to help out any friend that asks for help. And ranted in this general vein at me for a bit. While also saying, as he ranted, that we didn’t have to have this “whole talk” about this, but he…kept talking? And talking, and talking. I tried to acknowledge his feelings, but I also didn’t want to keep discussing it, and basically listened until he wore down.

We ended it with him feeling better, I guess? But I felt worse. More so because I felt like I was trying to give a sincere apology and recognize his feelings and then we could move on, but it turned into him becoming more annoyed, and that line about being “obligated” really hurt, I thought he was just being friendly, but it now that gesture feels tainted somehow.

Captain, I don’t think it would be helpful to talk to him about this, I think I have to accept that this is just my friendship with him. But I’m confused, why did he get so annoyed? Is there a way I could have apologized better?

Confused Navigator

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#1260: “How to maintain boundaries within stressful family relationships during COVID-19 lockdown?”

By
March 31, 2020
advice, boundaries, bygones, COMMUNICATION, Families, family, manipulation, Parents, Reader Questions, Relationships, self-care, THE FIELD OF NO FUCKS GIVEN
34 Comments

Hi Captain,

My mother and I have always wanted different frequencies of interaction. After I moved out for university, at a holiday party my mother announced the only gift she ever wanted from me was daily phone calls – even her friends were incredulous. She tends to call any hour of the day, hitting redial up to a dozen times if I don’t answer. Calls can be about anything, from “are you free tonight” to an extended vent session about my father or brother (who still lives at home). No call has ever been an emergency – I found out my father broke his wrist a week after it happened, via Facebook, despite my mother and I talking in-between.

Over the last few years, I’ve become better at enforcing manageable levels of communication – proactively calling her on weekends for a chat, making up vague excuses, explicitly saying I won’t answer/call back unless I’m free. This had the side effect of every conversation starting with how I’m too busy and don’t prioritise family. After the first few hour-long complaints, it’s now usually only a throwaway comment per call.

With COVID-19, we’re all under Shelter-in-Place. Now she knows I’m not busy and she wants the daily calls again. Additionally, she wants to use them to teach me her native language. Even if I didn’t find daily calls with my mother draining – daily phone calls that require homework and family/diaspora guilt?

I know we’re in anxious times and we should all reach out and connect with each other. I am also worried about my parents – my father is likely high risk, my brother maybe so, and my mother is a healthcare worker (not frontline, but still in a hospital).

I’ve tried suggesting using a language app/online course and having weekly conversation practice – no dice. I’ve tried suggesting weekend catch-up calls without the homework, but then comes the guilt. We text occasionally with pictures of the garden, but that doesn’t cut it. Digital game nights and Netflix-parties are also out.

I’m tired and stressed and I want to connect with my mother – but not at the expense of my own mental health. Suggestions? Scripts?

– At home doesn’t mean on-call (she/her)

Thank you

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#1257:”How do I navigate the transition between romantic relationship and friendship with someone who’s really (platonically) important to me?”

By
March 4, 2020
advice, boundaries, BREAKING UP, bygones, communications, crushes, Manners, Overthinking It, Reader Questions, rejection, Relationships, self-care, Social Interactions
100 Comments

Dear Captain,

I had a friend I first met about 15 years ago. We got on amazingly well: mutual friends called us “one mind in two bodies” because our personalities were so similar. We understood each other almost perfectly and could talk and laugh for hours about things nobody else quite got. We then had an extraordinarily intense romantic relationship: we were ridiculously in love and had an incredibly deep connection. It ended because I was super needy and honestly wasn’t ready for that sort of relationship. We were both heartbroken and intended to get back together one day, but life took us in other directions. We tried to stay friends but I wanted too much from him; he felt he had to keep me at arm’s length. I told him I had too many messy feelings to have a healthy friendship, he begged me not to go, I said I hoped to be back one day, there were tears on both sides and we went our separate ways. This was in 2008. Resolving to take something positive from what happened, I worked hard on myself, addressed the co-dependency issues that had driven ALL my previous partners away, and now I’m married to an awesome guy I’ve been with for 10 years.

This January, we finally got back in touch. I apologised for some hurtful things I’d said when I was in a lot of pain over losing him. I told him how I’d changed for the better. I said if he forgave me for being a jerk I would love to rekindle that awesome friendship if he wanted to, now Other Feelings weren’t an issue any more. He replied to say it was a lot to take in (naturally) but he would answer via email, not to worry if that took him a while and, in the meantime, how was I?

Since then we’ve exchanged several messages but often he takes days, even weeks to reply so we haven’t really got a good conversation going (except one night when we texted about random stuff until 2:15am, which showed we still have that great connection and same weird sense of humour). Because communication has been so sporadic, it’s hard to gauge what sort of friendship we might have if at all. When he does reply he’s warm and affectionate, laughs at my jokes and sends me cool stuff he knows I’ll like. But because of our complicated history I’m unsure how well I can walk the line between “yikes, co-dependent ex-girlfriend is messaging too much!” and not having enough contact to re-establish a friendship.

I’m trying to give it time – maybe he’s just not ready and could be navigating A Swamp of Unexpected Feelings himself. But I feel with this sort of situation it’s important to be honest and open from the start about what you want, like I was in my first message to him. I gently reminded him he said he’d email me and while he didn’t have to, I’d appreciate knowing where things stood between us. He said he was busy but could do it next week… which was several weeks ago now and don’t feel I can ask again. Me badgering him when he needed space was why we stopped being close in the first place.

I’m feeling a bit lost about how to handle this situation. At the moment I’m playing it by ear, replying to messages when they come, trying not to send too many back, giving him space when he doesn’t reply. But while I’m thrilled to be back in touch, there’s this elephant in the room, it’s…uncomfortable, and I don’t believe he’s going to send me that email – it’s been nearly 2 months. How can I figure out what the relationship is between us without making him feel pressured to talk about things he clearly doesn’t want to talk about?

Hopeful Friend

PS I searched for similar letters but the closest I found was you advising not to reach out to an ex for friendship until your feelings reached the point of “oh yeah him, I wonder how he’s doing, would be fun to catch up.” Which is what I did… but now I don’t know what to do next.

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#1253: Beloved, You Are Not “Torn,” You Are In Denial About Your Choices

By
February 24, 2020
BREAKING UP, cheating, Reader Questions, Relationships

Dear Captain Awkward,

I am torn and hoping you may have some options that could help me make a decision. I’ll do my best to keep it brief, but I want to do my best to give you as much to go on as possible.

Around 10 years ago, I met my future wife, we’ll call her “E.” Things started out pretty fast, she is very introverted and I am pretty extroverted, so I think we were both intrigued in learning each other’s ways and trying the other’s interests. Within about 3 months, things became pretty physical, pretty fast, if you know what I mean. This lasted for a little over a year, where we spent most of our time together, and most of it was alone. We tried going out with my friends, but she didn’t like them or going out, and I was okay at the time to split time between her and what I like to do, probably a 70:30 split.

After around 1.5 years of being together, I moved away to grad school, something I had been planning since we first met, so it was no surprise to her, but I was not ready to move in together and she was not ready to move and find new work, so we became a long distance relationship. We talked each night, but quickly ran out of topics, sticking to a 45 minute limit on conversations because we seemed to run out of things to say and I hated just sitting on the phone listening to each other breath.

We saw each other about 2 times a month, just for a weekend, which was typically spent mostly in the bedroom. She would become very upset about not moving the relationship forward when she heard of friends getting engaged, and often brought up marriage. When it came time for me to graduate (around 4 years into the relationship) I knew I either had to commit or break it off. I should’ve realized that having that thought was probably not a good sign, but I thought maybe it was cold feet and normal. I felt committed to her and didn’t want to hurt her, as well as this was as good as I had felt in other relationships, so what would be different if I ended it and tried starting new. I never felt that “falling in love” feeling I’ve see on TV/movies, or heard about from friends, and I have never been openly emotional or enjoyed PDA or even the DA part when 1 on 1 with a girlfriend. I have just never been super excited or felt thrill with the people I have been with.

Once we got married, she moved in, we got a puppy, she got a new job, and by the time a year almost rolled around, we were house hunting. Everything was just moving so fast, there was never much time to think. A month later, we found a home, moved in, and found out we were pregnant. Things were crazy for a year, but we both expected it, especially since the closest family is several hours away. She stayed home with the baby for 2 years before starting to look back into work. She also stayed in the guest bedroom every night for that whole period, insisting she would wake me accidentally when listening for or getting up with the baby, even though I encouraged her to come back to our room on day one. It was around the two year mark that I realized how bored I was with our life.

Sex had become a routine, once a week on Fri or Sat night, only after she had showered. It was even to the point she made jokes about how routine it was, I would try to spice things up or change it up, but she said she liked our routine. Our talks consisted of the baby and work, I would try to come up with things to do but she enjoyed just staying home and cleaning. I feel so anxious when I don’t get out, that I would take our daughter and do things with just the two of us, or on the rare occasion, just get out for an hour or two by myself.

This went on for another 2 years, slowly feeling like we were becoming more and more distant, barely talking, the only physical contact was our routine sex once a week. Sometimes I would pretend to not feel well to skip it because I just couldn’t get in the mood. I was afraid this was what my life would be like for the next 14 years and then what would happen when it was just the two of us again? But what else could I do? I considered divorce for at least a year, but I felt I had no good reason other than being unhappy, but I was growing used to the idea of divorcing and just doing life alone and with my daughter on the days I would have her. But also, would there even be a point in getting myself into the same situation with someone else if I never really felt that strongly for anyone before, I am in my mid-30’s by the way.

Then in June 2019, a female at work began to grow close, we’ll call her “L,” occasionally texting, chatting more than normal when at work (she only worked part-time, 0-3 days a week). But I noticed I would miss her on the days she was gone or when I didn’t hear from her. In July, the texting picked up to daily and throughout the night, to the point I would get notifications that I had burned through my data limit, and have stayed up past midnight, when normally I would’ve been in bed at 7:30 and asleep by 9. She was going through a divorce and dating, but I began getting jealous of her going out with these guys. Texts and talks seemed to get flirtier, until the point where she sent a topless photo, unprovoked, to see my reaction. I felt wanted for the first time in many years, and actually felt excited for the first time I could ever remember and I could not stop thinking about L. We had so much in common, it was like we could read each other’s minds. I had never felt a connection like this before, not even at the best moments with my wife or any other girlfriend. I felt happy around her, elated, like a whole new person, even just when texting her, it was an odd feeling for me but it was intoxicating to feel this way, I couldn’t stop, it was addicting. I wanted to be my best person for her, to improve myself, and spend every moment with her. My efficiency at work even declined because I was with her so much when she was working.

In August, L began to make statements about ending our talks, since she knew I would never be able to give her my all and vice versa, as well as become physical with her, and I felt my heart break. She helped arrange an after work party to give me an excuse to hang out in person, outside of work, and as a “last hoorah”. She came dressed in what might as well have been lingerie, and I felt like we were the only two in the bar. When we moved to another bar, she reached for my hand and I felt like I was floating, how could I have realized I that I was missing out on a feeling that was so incredible, why have I never felt this before, and why has my wife never made me feel this way before.

After a few drinks at the next bar, we both headed towards the bathroom and she told me she would not make a first move because I was married, but when I came out and saw her waiting for me, I couldn’t help it, I had to experience a kiss with her, and I had never felt anything like it. We fooled around under the table the rest of the night, and more in the car after. I ignored texts and a call from my wife and eventually took L back to her friends home. They invited me in, but I knew I had to go. After that, we began fooling around at work.

By September, she ended things because she knew it couldn’t go anywhere, and I spent that night sleepless and physically sick, I knew she was working the next day and avoided her area for hours longer than usual. Once I did go down there, I felt worse seeing her. It was extremely awkward and painful. By the end of the work day, she texted and asked to meet up, I did, and we talked about how horrible we both felt, and fooled around again. Not long after, she arranged another “work party” and we made love after, twice, something I had also never felt an urge to do before. I say “made love” because this was how it felt, this amazing connection, a type of sexual connection I have also never felt before. Usually after sex, I just want to clean off, and have some space, with her, I wanted to cuddle, go again, and never let her go.

I began “going out” more and started just going to her home when her kids were with their father. We would make love multiple times in only a few hours, something I had never been able to do before, nor felt the desire to do, I knew I had fallen hard for L but I was afraid to tell her because I thought it would scare her off. I would take days off work in secret from my wife, and spend them with L. I would have PDA with her everywhere we went, also something I never enjoyed before, but it was tunnel vision with this woman and I didn’t care about getting caught or not. I even hoped to get caught, to give me a reason to end things with E, I never hid my texting habits from E, and L and I both wondered why E never seemed to notice how much more distant I was becoming or how much I was communicating with someone else.

During all of this, I had been making excuses with E as to why I was not having sex with her, claiming migraines, stomach pains, etc., but one night in early Oct, I ran out of excuses, and it came a fight about why I hadn’t in months, so we tried to have sex, but I could not even keep it up, all I could think was I was betraying the person I really love. I discussed it with my new love later, only after L had asked about it, and she was of course hurt, but understanding that it would’ve had to have happened at some point since I was still married. I tried to explain that I couldn’t even finish, much less really perform due to how strongly I felt about L as well as how poorly I felt about my wife, and she seemed to understand and told me it was okay.

However, a few days later, she called and said it was over, I was distraught and felt sick again. I apologized for hurting her and said how much I didn’t want to lose her but knew that I had no say in any of this as I was the cheating husband and not her boyfriend like I wished I could be. A few minutes after ending our talk, she texted how she felt horrible because she was in love with me, this was the first time either of us had said it, I told her that I was in love with her as well and had been for months, as well as everything I loved about her. After a long talk, things seemed to be okay.

We made love one or two more times after that, then she became more and more distant, and eventually ended it mid October. The next day was similar to the first time, where we ended up catching each other by the end of the day and kissing but then she told me she could not keep doing this and was starting to date again. The following day, I thought things may have been okay and tried to kiss her when we were alone, but she pulled away, I never felt so hurt and like such an ass at the same time, I knew it was time to try to figure out my life or lose the person I love. L also told me the same thing, that I needed to figure out my marriage, if not for me, then for my daughter, to try to save it for her, because L wished she could have saved hers for her kids.

It was not long before I told my wife that I did not like how things were and wanted to go to couples counseling. She disagreed and said everything had been perfect for her, that this is the best her life had ever been, and did not understand why I was saying these things. All I could really say was almost the entire truth, that I had fallen out of love with her, it had been getting worse over the last 2 years, and I’m at a point where I’m depressed and don’t know what to do. This went over horribly and started many fights, but as I told her more and more about how I felt like we grew apart and were just roommates, giving her many examples such as; she hadn’t sat in the front seat with me but 3 times that year (because she always chose to sit in back with our daughter), and those were the 3 times my parents were in town and we went on a “date.” Dates consisted of groceries once, a movie and back once, and then shopping once, I pointed out how she showered every other night or sometimes went longer, she had not gotten any new clothes in over a year and only wore the same two outfits to bed which were falling apart, she never tried to dress up for me or show that she cared about how she looked with me, that we had not held hands in ages, etc. After many fights, she seemed to finally get it, and agreed to counseling a month later.

Counseling has been difficult as I really want to say that I cheated and am in love with someone else, that I haven’t ever felt so loved and so happy, even at the best times with my wife. But even as much as I want to end things, I don’t want it to be because I cheated as I know that would be held over me for the rest of my life (as it probably should). When asked if I want to make things work, I just agree, but wish that I had the courage to say I just want to be with someone else, and if that’s not possible, I’d rather be alone.

As Nov passes into Jan, at work I hear about L’s new partner, he calls during work and texts all the time, it kills me to see the smile and laugh he gets from her, I loved being the one to get that and still do, it’s torture, but I can’t stop being near her. I tried my best to avoid her, but then she seemed sad and asked me if things were awkward, that she missed me and us but that it couldn’t have worked because of me being married and she didn’t want to be the reason I ended my marriage, to be the “other woman,” to have my daughter know it was L’s fault that her parents split, etc. I told her I was trying, but she knew the problems I had with my wife prior to getting together. She told me it was not fun to be divorced, and to just make it work.

L started to text me more towards the end of Dec, something which confused me, but made me so happy at the same time. I was in almost daily fights with my wife, to the point E told me she knew I wanted a divorce and to just do it, I was excited when she said this, but scared of the reality as well. But I didn’t know how to respond and said that we should discuss it in counseling. By the time we did, E had already changed her mind 15 times.

During Jan, I met with L several times outside of work, but only as friends and never tried anything more than a hug. We talked about missing each other, her boyfriend, my wife and issues, our kids. I even told her how at one point during all of this, E had talked about killing herself because she was so upset with me and our life. L and I had become so close, she was my best friend while we were lovers and I was just so happy I had a piece of her back, I didn’t want to lose it.

Since Feb, my wife and I have gotten back into the “safe” routine of only talking about our kid and work, counseling has become more fluff than real topics, and we tried a weekend trip in which the best 4 hours of the trip was our drunkest in which we discussed what we would do if we divorced, killed each other, or something happened to the other. This was the most talking we had done in years, and the happiest I think either of us had been together in years. However, it still felt to me like talking with a friend, no romantic feelings, no desire, no real want to even continue the night after that talk.

Once we had gotten back to the room, we discussed how neither of us wanted sex still (we have not been together physically since I was unable to perform in Oct.) since she knew I didn’t love her and wasn’t attracted to her, and that was how I felt too. That ended the night and made for an awkward morning and quiet trip back.

I’m pretty sure I don’t have a chance with L anymore as things have been going steady with her new boyfriend for several months now, as well as I don’t think she would trust me even if I was divorced and poured my heart out to her, as now I have the label of cheater, even though she is the only person I ever thought of cheating with. Before her, my sexual dreams only involved my wife, but after her, I have not had a dream about my wife since, and had nightly dreams about L for months, and even now I have them every couple of nights, but they aren’t even sexual, they’re dreams of laughing together, hanging out in public places, eating dinner, and I always wake up in such a great mood from them, until I remember it was just a dream but I do my best to hang onto that memory as long as I can.

I don’t think I have a chance at happiness with my wife either, as I cannot get L out of my head, nor all the horrible things my wife has said to me and the horrible things I have said back, as well as how horrible I know she feels every day, knowing that she is with someone who is no longer in love with her nor attracted to her. She is a good person and does not deserve this, and my daughter deserves to see us both happy, for hers and our sake.

I’m at a point where I think being alone may be the best decision for my daughter and I, giving her mother a chance to find happiness with someone else sooner. Then maybe I would be able to reflect more on myself and what I need, if someone could make me feel so amazing before, I need to find that high again or just settle for being alone to be happy. I’ve also recently come to the realization that I have always had very close female best friends (none of them were ever anything physical nor anything I wanted to become physical, except when L came into my life) and I believe now this has been because I have never felt like any woman I have been with was my best friend and I sought that out in others. I would also like to add that I’m still surprised I have never felt guilty about the affair with L, only guilty about the one time being sexual with E and that was guilt for betraying L.

I apologize for the length of this, and thank you for reading through it, although I know it’s as clear as mud. Please, any thoughts/opinions on what to do are greatly appreciated.

Sincerely,

Torn

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#1247 “I went no-contact with my mother and it’s turned her into a bogeyman”: Anxiety, Anticlimax, and the Aftermath of Estrangement.

By
January 21, 2020
Abuse, boundaries, bygones, control, emotional abuse, Families, family, Manners, Mental Health, Overthinking It, Parents, Reader Questions, Relationships, self-care, Social Interactions
197 Comments

I’ve gotten a bunch of letters about family weirdness and estrangement and boundaries (weird, almost like there was a series of events in the last month that forced a lot of family togetherness, can’t think would have caused all these old wounds to re-open at the same time? 😉 ) and I’m going to put up a series of them this week. This one is about the aftermath of cutting ties with a parent and the still-present worry that running into them will be awful.

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#1246: “Partner with lots of expenses and little income.”

By
January 18, 2020
advice, boundaries, Dating, ethics, Feminism, manipulation, Reader Questions, Relationships, self-care, the art of no
1 Comment

Hey Captain Awkward.

I read some of your responses to other writers who had concerns about their partners’ finances, and I feel like this is related but not quite the same.

I’m stressed about my boyfriend’s money management skills and how I can help him without getting myself into a bad financial situation. I also recognize that he’s probably embarrassed on top of being stressed, so I’m trying not to make him feel ashamed. He was raised below the poverty line and when he made it “big” in his industry, he was earning huge salaries, so I think he’s allowed himself to fully enjoy it. Now he’s unemployed but is still living a “huge salary” lifestyle.

About me: I’ve always lived pretty frugally. I’m kind of a prepper in some ways – I buy a lot of dried or bulk foods, and I park nearly a mile away from work and walk every day so I don’t have to buy a $400 annual parking pass, plus I get some exercise which is hard to come by in my 9-5 cubicle lifestyle. My mortgage is manageable, 90% of my furniture is thrifted (thank god eclectic/Boho decor is “in” right now), I pay my bills on time, I have a modest emergency savings, and I have excellent credit — with a little bit of revolving credit card debt. My house is my first home purchase, and in addition to receiving some assistance from my grandparents, I participated in a federally funded first-time home buyer program and saved for years to come up with the down payment. My house isn’t fancy, but I love it because it’s mine goddamnit, and after changing addresses every year for 18 years, I finally get to lay down some roots! I‘ll hit my one-year anniversary of homeownership next week. Yay.

I do not typically seek out partners with tons of money. In fact, I’ve been known to date transient wildlife biologist types who briefly stay in the area to work for six months out of the year, and then squirrel their earnings away to get by the other six months. I just happened to fall in love with my BF who – up until last summer – was successful in his career, made a lot of money as a senior level designer with some recognizable household brands, and was promptly relieved of his duties the same week we met. He felt it was a blessing in disguise because he’s burned out on doing design for a living and wants to pursue his passion of selling rare European cars.

BF was earning a gratuitous salary last year, and while he lived within his means, said means were extravagant and now unsustainable: he owns two houses and has 7 cars (or 8? I actually don’t know anymore). Again, cars are his hobby/passion, as well as his side business, so some of this is to be expected. Two of them are “investment” items that will continue to appreciate in value, two are for driving, and the rest are “projects” that he plans to sell… but as you might imagine, this ties up a lot of capital in non-liquid assets.

BF is hemorrhaging money, but not cash, and is putting a lot of charges onto credit cards. He justifies this by saying that most entrepreneurs fund their businesses through credit. BF also owes his best friend a sizable amount for a recent generous loan which seems to have strained their friendship a little.

Three months ago, BF put his second house, which is in a popular resort town a few hours away from where we both live, on the market. He’s received multiple offers on the second house, but due to complications beyond his control, they continue to fall through, and so it remains on the market. BF was relying on the sale of this second house to kick-start the car business.

His monthly expenses (e.g. mortgages, private school tuition for his two kids, and commercial space for his new business) are over $5k. Not included are utilities, groceries, gasoline, health insurance, pet expenses, or anything else fun/recreational like an occasional meal out or outing to the nearby large city. BF has very little income right now except for infrequent freelance design work which he loathes and the car side hustle. Currently, he sells a car every 4-8 weeks and each sale results in a few thousand dollars. I in believe he’s receiving unemployment, but I’m not sure that he’ll qualify for much longer.

I told him he could sell his primary house and move into mine if he wanted. My mortgage is literally half the size of his, and if he paid HALF of my mortgage he’d still save $2k/month. However, he doesn’t want to sell his primary residence for a lot of (legitimate) reasons, and he wants to keep trying to sell the vacation home that’s been on the market for four months. OK, I get that… But right now, it’s just him and his dog occupying a 3,000 square foot space. He wants me to rent out rooms in my house and move in with him (I would contribute to his mortgage, which would only cover 25% of his monthly payment). I am considering it, but I’m also so happy to finally have a home of my own… it would make me sad to move out of my first home so soon.

I know he’s filed for bankruptcy once before, and he recently said he doesn’t want to do that again (he said it semi-jokingly, so I don’t know how much of a real possibility it is for him). He also told me early on that he thought I’d be a good influence on him as far as spending habits go. These were yellow-orange flags for me at the time. Now, he’s asking me to go with him to a cousin’s wedding on the absolute opposite side of the country in two months. We both have airline miles that will cover the trip, but it’s honestly not how I want to use those miles — the whole reason I got a credit card that gives airline miles is because he suggested I get one so we can travel overseas together this year. I wouldn’t have taken out a second line of credit if I didn’t think we weren’t going to use it for an *international* vacation. Plus, the wedding trip in two months becomes more expensive when you add up the other items that will not be covered: lodging, dining out for five days, hiring a pet sitter for our two dogs, rental car, etc. And I’m also just feeling less and less secure about out future together as the weeks roll by. Like what kind of message would I send to his family by attending this big family event if I’m not sure how into/secure I feel about the relationship by the time the wedding rolls around?

He has also half-joked about how I should have offered to pay for a recent ticket he got because he’s so broke. (He wouldn’t have received the ticket in the first place had he agreed for us to take my car that morning — which gets twice the MPGs — instead of his… but he insisted on taking his car. It apparently didn’t have a front license plate which resulted in a ticket.) The irony is that I almost offered to pay for it as a “sorry you’re broke, happy belated birthday” gift… but after he said that, I thought “NOPE. Nevermind; I don’t owe you shit.”

Let me preface that BF is the closest I’ve found to “my person”, if you get me — our connection, chemistry, and compatibility are mind bending. I’ve dated a lot of people in my day and never felt about them the way I do about him. I want to live with him at some point, get married, and maybe even have a child. How can I communicate my concerns to him without compounding his stress and sounding like a tightwad? (Also… Am I a tightwad? I’m starting to doubt myself and my saving habits…) And how do I support him without getting myself into a bad financial situation of my own? I don’t want to lose my savings, wreck my good credit, or be his cash cow, but I do want to be there for him in a way that empowers, not enables. I can see a future with him… so do I just sit tight through this rough spot and hope it all works out soon, or am I aboard a sinking ship and just don’t have the perspective to see it? Also, is there a way I can get out of attending this wedding?!

Thanks Captain Awkward!

Hello! I am so glad you wrote!

And congratulations on this month’s award for “burying the lede”! I retained the subject line of your email as the subject line of the post because I wanted readers to ride the same “oh, only 7 cars? Or is it 8?” roller coaster I did. 🙂

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Image: A certificate for excellence in “buring the lede in an advice column letter”

You have been so candid and such a good advocate for yourself that it makes my job very easy. My advice is:

  • Do not jeopardize anything about your finances or housing to “help” or “support” a man with 2 houses and 7-8 cars. 
  • Re-examine the idea that it is your job to help him figure out his money & his relationship with money. 

I’ll elaborate but here are some scripts:

  • “I do not want to move out of my house.”
  • “I do not want to move out of my house to make housing payments on a house I don’t own.”
  • “I’d rather save my miles and money for a vacation than go to that wedding, and I can’t afford to do both, so you’ll have to fly solo on that one. I’ll have to meet your family some other time.” 
  • “We approach money really differently, and I do not think it will be good for either my credit score or our relationship if we combine money or housing, especially while you’re still getting your business off the ground.” 
  • “I want to help you through this, but ultimately it’s your money and your decision, so one way I can ‘help’ is by having really clear boundaries especially around financial decisions that affect me.” 

Additionally, scriptwise, be very blunt and specific about money in your dating life. Do not let this flounder in expectations and hints, get in the habit of nailing stuff down like where are we going, what is the anticipated cost, who is paying. When you are offering to pay, make that offer up front: “Can I take you to ____ tonight? Dinner’s on me.”  (This is a good thing to do anytime you are treating a known poor-er person, the anxiety of guessing and mentally running the budget numbers is just awful and fun-destroying). When you are splitting costs or expenses, settle up right away. “The bill is ______, do you want the waiter to split it for us or do you want to pay and I can Venmo (etc.) you my half?”

This may seem unromantic and tedious, and it might bring out some weird shame behaviors and avoidance in him, but do it anyway. If you can’t afford something, say so. “That sounds nice but pricier than I can handle right now, can we save it as a treat for next month and stay in tonight?”  Make this shit matter-of-fact and normal. Make yourselves a couple who can talk frankly about money in mundane, routine ways that doesn’t require big negotiations or emotional processing.

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