DEAR DR. NERDLOVE: My boyfriend and I are in our mid-30s have been together for 13 years. I love him dearly and we get along great. My life with him is truly the happiest I’ve ever been. We have no interest in getting married or having children as a personal choice, but are looking forward to having a long cohabitating life together. He’s truly a sweet, loving, and hard-working guy.

However, he isn’t financially responsible.

For a bit of context, I grew up in a low-income home and he was raised upper-middle class. We are currently a middle-class working couple in different careers, but make almost the same amount of money. We also live together in an apartment and share all of our bills equally. However, everything is in my name in order to ensure that everything is kept up with and paid on time. I wish I could share that burden of responsibility, but I can’t. I have retirement, non-retirement investment, and savings accounts. He does not. I have my financial paperwork generally organized and in one place. He does not. I occasionally check my account balances and credit score. He does not. When I make a big purchase, I do my research. He does not. I pay my expenses by the deadlines. He does not.

He’s not a lavish over-spender and has enough money to take better care of his finances, but just doesn’t care about it and neglects these (and other) responsibilities either entirely or until the last moment. Even when he faces consequences for his indifference (like losing $1500 because he forgot to fill out a piece of paperwork on time, has to pay late fees for expenses that could have been easily taken care of in advance, or loses his tax documents for the 4th year in a row and having to pay everything to be re-printed) he doesn’t make any changes, is completely unfazed, and makes the same mistakes over and over.

We’ve never argued about money, but I want to make sure we are protecting ourselves and each other. I’ve tried to talk with him about it a few times and find some solutions, but those conversations never go anywhere. He’s not mean or openly dismissive. He just doesn’t seem concerned or feel any urgency to make changes. This isn’t an issue that affects our day-to-day life, but it does come up sometimes.

What do you do when you care about someone, but they lack any desire to develop financial insight? Should I just let it go and focus on me while he hurts himself?

Bad Credit, No Credit, Big Problem

DEAR BAD CREDIT, NO CREDIT, BIG PROBLEM: So I’m going to be honest: this sounds more like a conflict in approaches to lifestyle than it does an actual relationship problem. From what you describe, the issues he has with, say, paying late fees or costing himself more money because of missing filing deadlines are inconveniences for him rather than issues that mean the difference between actually being able to pay the rent each month.

This isn’t to minimize your concern, BCNCBP: money and the stress that comes from dealing with finances is probably the single greatest cause of relationship strife out there. Whether it’s a significant imbalance in who’s contributing how much to the household finances, one partner blowing their cash from the joint checking account on lavish indulgences or simply dragging their partner’s credit into the mud, money ranks at the top trigger for break-ups, even beyond cheating and sexual incompatibility.

But that doesn’t sound like what’s going on here, exactly. It sounds like you two haven’t co-mingled your finances, your boyfriend isn’t sponging off of you to live the lifestyle to which he intends to become accustomed and you’re not at risk for his tanking your credit score. Instead, it sounds like things are divided between “I wish he was a little more analytical” with things like big purchases and a desire to see him be more responsible with actually getting his bills paid on time.

That’s why I’m gonna be vulnerable here BCNCBP: I’m a little like your boyfriend. I’m not exactly the most organized guy you’re ever gonna find. I have a tendency to do the last-minute scramble when it comes to things like bills, taxes, important appointments…

(And I think I hear my editor very pointedly sending me that Douglas Adams quote about the sound deadlines make as they woosh by, even as I write this)

For me, this is because I have a nasty case of “out of sight, out of mind”. I’ll have a brief period of “ok, I’ve got to remember that I have to do X thing by Y time,” where I resolve that I’m going to get everything done exactly when it needs to be if not beforehand… and then I fall down the research rabbit hole because I suddenly had a shiny new idea that’s shoved everything else aside and occupies the entirety of my attention. My good intentions tend to fall by the wayside in a sort of benign neglect.

Now I’ve been lucky. The worst consequences I’ve faced have been the brief panic of “oh crap oh crap oh crap where is everything” or running out the door with coffee in one hand and a piece of toast shoved in my mouth as I realize I’ve got to make a 20 minute drive in 5 minutes. Not fun, exactly, but not terribly dire either. But I have had a few close calls that’ve been enough to make me try to find a system that works for me. And here’s what I’ve learned about dealing with issues like chronic tardiness with one’s bills:

Sometimes the path to success is the path of least resistance.

You can’t force someone to develop a sense of fiscal responsibility or switch their personality to match yours. You might get them to try something different for a little while, but they’re going to slide back into old habits the moment that you aren’t there to constantly reinforce the change. All that’s going to do is cause annoyance and resentment on both sides.

What you CAN do, however, is help set things up to work with and around your boyfriend’s flaws. Since the issue here is that your boyfriend is just bad with due dates, rather than being chronically short on cash, you can help him set things up so he can’t not be late. So it’s time for some better living through technology and outsourcing some of life’s repetitive annoyances to digital assistance. First, start with automating everything you can. One of humanity’s greatest inventions is being able to set up automatic recurring payments. Setting things up to, say, have the utilities company charge your (the generic “you”, not YOU, BCNCBP) credit card every month helps make sure that you’re never going to be in danger of the electricity being shut off.

Those same automated charges and options mean that you and your boyfriend can set things up so that he’s less likely to be late on the bills.

If you want to make sure he’s always getting his share of the rent and utilities to you on time without nagging him, you can set up recurring monthly transfers via his bank, PayPal or Venmo. This helps ensure that he holds up his end of the arrangement without your having to feel like the nagging, shrewish killjoy who’s always dumping on her partner’s good time.

Similarly, you can set up automated systems to help do things like “keeping his financial documents in the same space”. If he can arrange to go paper-free and get electronic delivery of his important forms, then you can set up filters on his email that will direct those files to specific folders, helping cut down on the last minute scramble or having to contact people to get new copies of important documents.

And for those appointments, deadlines or other events that tend to float in one ear and out the other? Set up recurring – and annoying – reminders in a calendar app, preferably one that syncs across all his devices. Quite possibly in triplicate. Having notifications repeatedly pop up to remind him that he has to be at X place at Y time helps cut through the distractions and keep his responsibilities at the forefront.

It isn’t a perfect system to be sure, and it requires some dedicated time to set it up and make sure he understands where all the various gears and levers are… but it’s worked out pretty well for me. It may well work out for him.

But otherwise? Yeah, unfortunately, this is going to be a price-of-entry issue for the relationship. You’re a little more rigorous than he is, and that’s unlikely to change. If you don’t want to take on a secondary job as his financial advisor – and that’s not your responsibility – then there’s not much to be done. You can help him set things up to mitigate his absent-mindedness, but at the end of the day, he’s the only one who can decide if he wants to do things differently. Thankfully, the consequences have been annoying, rather than disastrous. Hopefully that’s an annoyance you can live with.

Just make sure you don’t put yourself in the position where his lack of responsibility drags you down with him.

Good luck.

Please send your questions to Dr. NerdLove at his website (www.doctornerdlove.com/contact); or to his email, doc@doctornerdlove.com)

DEAR DR. NERDLOVE: I (19/m) recently confessed my crush to an online friend (21/f).

For about 4 years now I’ve been very close to a friend of mine online. In fact, we’ve been so close that I’ve had a crush on her for 3 of those years. Even when I had a relationship with someone else, the feelings kept surfacing no matter how hard I tried to push them away.

After I broke up with my then girlfriend, I felt the intense need to finally tell my crush how I had felt about her. I waited a few months to do this, since I didn’t want to  just jump into it after a break up. Of course, I was hoping for a positive outcome, but I ultimately didn’t mind if she didn’t want to pursue a relationship. I just wanted to be honest about how I felt about her. 

Her response consisted of asking me how long I felt that way, a lot of awkward stumbling (I was much the same in the matter), and saying that while she felt really REALLY happy,  she didn’t think anyone would ever like her, and that she didn’t want to jump into things without thinking it over for a few days. I was totally ok with this.

Now it’s been over a month. We still talk daily, exactly as we did before I told her. I’ve tried to talk to her about things, but it’s always met with silence, and a subject change. The closest I’ve ever gotten was an “I still don’t know”.

I’ve stopped trying to talk about it, because I don’t want to be an asshole who keeps trying to shove her into an uncomfortable situation. But it’s getting to me emotionally and hitting my anxiety. I suppose I just want closure, a yes or no instead of this radio silence I’ve been getting.

At this point, I understand that it’s a no, and I can accept that. My best guess is that she doesn’t want to risk hurting my feelings or making things weird; though I’m not actually sure of course.

I guess in the end I’m asking “What do I do about that?”. Do I simply leave the subject matter alone and accept it? Or would it be better to force the conversation to happen? I feel like a massive asshole in this situation overall honestly.

– Just Want an Answer

DEAR JUST WANT AN ANSWER: Before we get to your question, JWA, I want to point out what you did wrong here: you made the classic mistake of just confessing your crush, and leaving it at that. While there’s a lot of stories in pop-culture where people confess their crushes on people, in practice it’s probably the worst way you can go about it. Not because there’s anything wrong with having a crush on someone, or even acting on it, but because all you’re doing is dropping this information in their lap like a cat bringing it’s owner a dead mouse. When somebody just confesses their feelings, what they’re saying is “OK, here’s this information… now what are you going to do with it?” That puts the other person in the incredibly awkward position of having to decide how they feel and how to respond. In a very real way, it’s putting the onus on them to decide the future of your relationship, which is a hell of a lot of pressure when they may have never even thought about it before.

This is why my general rule of thumb is that, rather than confess your feelings, the best move is to ask them on a date. It doesn’t have to be terribly elaborate or profound, just “hey, I really dig you and I’d love to take you on a date; how would you like to go do $COOL_THING on $SPECIFIC_DAY?” This is a much lower – and more reasonable – ask than simply telling someone “hey, I have feelings for you”; a date isn’t an invitation to reconsider an entire relationship, it’s an entry level exploration of whether there’s any chemistry or interest.

Now granted, this is more difficult when you’re dealing with a strictly online relationship. It’s a little hard to propose a date when you haven’t even met, nevermind don’t live in the same city (or within a reasonable distance of one another). But I’ve written before about online only relationships, but the short version is: if you haven’t met in person, then you’re not dating. No matter how well you may know somebody or how much chemistry you have in text or even in Skype, none of this guarantees chemistry when you meet in person.

So while I don’t doubt that she’s an important person in your life… declaring your love for her is honestly a little premature.

(And honestly? I don’t think you’re an asshole. You’re just young and enthusiastic and you took the route that was a little less than perfect and that’s ok.)

But hey, that’s all for the next time this issue comes up. Your question is what do you do now?

And the answer is… nothing. I mean, I hate to tell you this chief, but you got your answer. You already know that. Hell, you said that yourself: this is the definition of a “soft no”. She doesn’t want to say anything because honestly, she doesn’t want to make things any more awkward than they already are. There’s not really anything else to say, and your bringing it up just makes it more uncomfortable.The best thing you can do is accept that she’s not interested in you that way. And hey, that’s a damn shame; it always kinda sucks when the people we have feelings for don’t return them. But the fact that she doesn’t love you the way you’d prefer doesn’t mean that she doesn’t love you as best she can. Being her friend may not be what you hoped for, but that friendship is pretty damn awesome.

Were I you, I’d just take the “no, thank you” and move on. If you do need to say anything… well, the best thing is to say “hey, I realize things are a little awkward right now, but I want you to know, it’s all good and I’m willing to power through the awkward if you are.” And then just drop the subject. If she ever wants to talk about it, she’ll let you know.

Good luck.

DEAR DR. NERDLOVE: A few weeks ago I wrote in about my friend Sarah. Taking your advice, I scheduled a trip with her last month and made it a point that we had to talk about us.

I'm happy to report that both the trip and conversation were a success. We agreed that we both had developed feelings for each other over the time spent together but we each had held our tongues for similar reasons. She confirmed she had caught the feels and was thinking about what it would be like to get serious, but when her family member unexpectedly passed away it threw her life into disarray and she realized our lives weren't going in similar directions - which I agreed with. We agreed it was best to remain friends and she encouraged me to get active dating. I wished her all the best as she continues to deal with the family issues at home and reminded her that she has friends here that care for her. As for the trip itself we had a blast and continued to be physical.

I have mixed feelings about the outcome of course but recognize it is for the best. We remain close friends and we're staying in touch. I want to thank you and the community for the comments which encouraged me to finally get the closure with Sarah.

Currently, I'm back in therapy. Even with the confidence I gained from my time with Sarah it's not enough to calm my nerves and get comfortable around people. I still need to work the anxiety that continues to hold me back from actively dating. The work continues.

Hanging By The Telephone

DEAR HANGING BY THE TELEPHONE: Thanks for letting us know how things were going. I’m glad that your trip was a success, even if it wasn’t necessarily the outcome you’d been hoping for.

In the meantime, you’re on the right track: taking care of yourself and working on your anxiety issues is absolutely the correct choice.

It ain’t glamorous or even terribly fun… but by the end, you’ll be in a much better place. And, even better: you’ll be ready when you find another opportunity for love and connection.

You’ve got this HTBT.

All will be well.

Please send your questions to Dr. NerdLove at his website (www.doctornerdlove.com/contact); or to his email, doc@doctornerdlove.com)

DEAR DR. NERDLOVE: I would like to thank you for all the great tips and information that you have given over the years; it’s been extremely useful. I just wish I knew about your work sooner, because I am going through a break up situation that could have been different if I knew the things I know now after reading your guidelines.

I would like to ask for your advice on my situation. Let me sum it up for you:

Summer 2015:

I met this girl in a summer program at my college. We connected immediately and we were together for 10 days until the program ended. We both knew that this was not going to go any further because she is from a different country, but we kept in contact.

January 2016:

She met a guy and they started a relationship and I was happy for her. I decided to go my own way and try meeting other girls too, but she had left an extremely high standard that no other girl ever met, and I would get disappointed every time.

September 2018:

She’s been with her boyfriend for almost three years, but we never lost contact. When we’d text, I would made sure to let her know that I’m still attracted to her and she started to flirt back with me. I wasn’t sure what to do, because she was still in a relationship and I didn’t want to be disrespectful.

By this time, I had moved to NYC to work , while she was in still in college in her country with 3 more years to go.

October 2018:

In our conversations, she let me know that things had been going badly with her boyfriend. I was trying to be there to support her, but to be honest, I was also there to see if I had an opportunity with her.

January-February 2019:

Our conversations had became very intense and shortly after she broke up with her boyfriend. She let me know that she is interested in me and shortly after we started a LDR. I didn’t know anything about LDRs, but I thought that we could make it work.

April 2019:

We were doing well for two months, talking and texting all the time, having our ways to show our feelings, having cyber sex to make up for the lack of physical contact and much more. We planned a trip for June in which she would come to NYC and stay with me for 2 weeks. In April, her school workload had increased and we started to reduce our frequency of contact. I got scared and asked her what was going on and she said that everything is fine, it’s just the amount of work that she had to deal with.

May 2019: 

Our conversations diminished quite a lot but I was patiently waiting for her semester to finish and get back to where we wer… but that never happened. She kept being distant, and one day she called me to break up with me. To summarize the call, she said that I never did anything wrong, that we would be together if we were in the same place. But  she hadn’t realized how much she needed the physical contact in a relationship, and this LDR was not working for her. She also mentioned that she is still coming in June, but she’s not staying with me and that she wants to see me at least once. For the trip, we had reserved a car to pick her up at the airport, we have tickets for a show and a concert. We decided that we would not waste that money and meet up on those three occasions.

Now, it has been 4 days since we broke up, we ended in good terms, we never fought or anything, and she asked me to be friends because she would like me to keep being part of her life. I told her that it’s possible, but I would never see her just as a friend.

I found your website a few hours ago and I read the sections and I realized that our relationship was doomed from the beginning and now, I’m not looking for trying to get her back. Although, here is where I am kindly asking for your advice.

Do you think that it is correct to meet up when she comes to NYC?

If so, how should I be with her when we meet? And texts?

Do you think that it is fine to try to be friends from now on?

Thank you in advance, 

Regards,

Loved and Lost

DEAR LOVED AND LOST: I think you’re going to have a hard time if you meet up, LaL. To be honest, I’m not entirely sure that keeping your plans to meet up at ALL was a good idea; it may have been a better plan for one of you to reimburse the other for their share of the tickets, cancel the car and generally just try to avoid one another while she’s in town.

The issue here is that you’ve spent the better part of three years yearning for her and four plus months in a long-distance relationship… none of it in person. That’s a long time to build up fantasies of your eventual reunion. To have the hopes of a grand, romantic encounter dashed… well, that’s going to leave a pretty serious pall over seeing her. It’d be one thing if you’d had more time to process your feelings and get used to the new relationship you two have… if you are even going to continue having one. I mean, you’re looking at the culmination of the hope of years, only to have them dashed at the last minute. I’m not gonna lie: that’s the sort of thing that can make getting together pretty damn uncomfortable.

Like, really uncomfortable.

Seeing her right now is going to be a reminder of what you had.. and don’t have any more. Is that something you’re willing to deal with if you see her? Are you going to be able to compartmentalize enough that you can see her and spend time with her without seeing the ghosts of futures past? Are you able to let go of what might have been?

But then there’s another issue: what about if things go well? I know, I know: what’s so bad about things going well and everyone having a good time? Well, the potential complication is that the point of failure in this relationship was that lack of a physical connection. And here you are in the same city for the first time in years. It could be that seeing each other could rekindle some feelings and you two may see about whether you have the chemistry in person that you had in text. Maybe the two of you will be all over each other like a pair of socks in a dryer.

That’s where things get complicated, especially if you’re not the sort of person who can easily separate sex from love. If the two of you do hook up, then you’re in the awkward position of asking: what now? Was breaking up the wrong move? After all: you’re still living in separate countries; you’re still stuck with the same, almost impossible barrier that broke you two up in the first place. Trying to get back together is going to end with the dance remix of your first break-up.

Now, maybe it’ll all be ok. After all, you had a relatively amicable break-up. It wasn’t anyone’s fault, just a case of circumstance. But it’s still pretty damn soon and the wounds are still pretty fresh.

Unfortunately, I’m not the one who can tell you whether seeing her is a good idea. You’re the one who’s going to have to weigh the potential pain against the joy of seeing your friend again. If you do go, I’d suggest keeping your expectations low; focus on just enjoying spending time with an old friend rather than what might have been or going over the break-up.

Is it ok to be friends? Well… yeah. I’m all in favor of being friends… if you can honestly be friends. If you’re going into this new friendship with hopes of getting back together with her, then all you’re doing is opening yourself up to future heartache. By the same token, if staying friends with her is like knives to your soul and getting your heart broken again, then it’s better all around if you end it.

Either way, I would suggest that you give yourself some time and distance before trying to be close. Even if you have the best and purest of intentions, you need to let those wounds heal before you can really make a friendship work.

Good luck.

Please send your questions to Dr. NerdLove at his website (www.doctornerdlove.com/contact); or to his email, doc@doctornerdlove.com)