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Hi, Cappy! I recently discovered your column and am so grateful for it. You’re amazing and helpful!

I really could use some situational advice, but it’s a long and complex story, sorry!

I’m a single parent of a 1st grader. Child support basically doesn’t happen.

3 years ago I was (thankfully) laid off from my research position. I’d worked hard after grad school to achieve success in an almost exclusively male-dominated and competitive field, but it was hard to raise my daughter working the crazy hours and with the amount of travel required for my job.

As a result I returned to school for graphic/web design; a field I thought would provide me with a more flexible schedule, increased job opportunities and potentially more money. I started a two year program at a technical school, with tuition and childcare 100% paid for by government benefits.

Enter “Donny”. Donny was a friend who was a neuroscientist at the University I’d attended and worked at. Despite having very different values, he had become a trusted friend. Romantic interest in Donny = 0. Divorced and childless, he is middle aged. He seemed kind and supportive when I really needed that. He was also the only positive male role model that my daughter had. He was not very involved in our lives at this point.

Donny started a tech company outside of his university position and became wealthy enough to retire from the University this year. He has a low emotional IQ, lots of anxiety and few friends. However, Donny loves my daughter and dotes on her. I don’t think he has ever said “no” to her. I’ve never had weird “vibes” about his relationship with my daughter. She was like the daughter he’d always wanted.

Back to me. Two years ago, after finishing year 1 of my program, Donny convinces me to drop out of school and work with him at his tech company instead. He says I am wasting my time at school and that he, the wealthy and successful entrepreneur, would teach me “real-world skills” and his special coding “secret techniques” from start to finish. He told me people would pay lots of money to learn his secret and that I was lucky he was willing to share this very profitable knowledge with me. He started paying me to do small projects, such as writing copy and some print work for his company. I was thrilled, thinking I was embarking on a new, lucrative and fulfilling career.

Fast forward to a year ago. Donny has stopped sending me any work but continues to pay me a barely livable wage each month to essentially do nothing. Projects are always just over the horizon but wind up “falling through” at the last minute or he doesn’t have the time to teach me anything because it’s a rush job, etc…. I make barely enough to cover my bills most months, but through decreased spending, I can still live check to check. I am ridiculously busy parenting (with no breaks), trying to stay organized, maintaining/improving my small house so my daughter has an un chaotic place to live, and being involved with my daughters activities while occasionally making stuff, but I have no social life (unfortunately that often goes along with single parenthood). I would like to make more money, but confess I am also enjoying the opportunity to be there for my daughter since I am her only family and her whole world. We are very close.

Donny continues to point out how rich he is, but keeps my pay at poverty level. He is also increasingly manipulative and controlling with his money, even believing he is entitled to having input in decisions I make about my and my daughters life, parenting, my house, friends, etc. He is by nature condescending and a master mansplainer. I ignore him and avoid confrontation because after 3 years of rarely seeing my daughter I still feel lucky to have this opportunity.

A month ago I ask Donny for more money for the first time because bills are mounting. I know I need to start a job search, but have been putting it off because —what the hell do I do now?

Donny tosses out a figure 33% higher than I’ve been getting monthly. He says he could even pay off my student loans “if he wanted to”. (They are not getting paid because I don’t make enough to pay them.) He tells me to send him the amount I owe and he will pay them off because he “doesn’t want the government to play any role in my life” which sounds generous, but is actually paranoid and a little conspiracy- theory ish. I send him the figure and he ignores me. All three times. I don’t rock the boat, but never even get a response. When that month’s check arrives its less than the amount he’d promised. I don’t say anything, feeling grateful to get anything at all, but irritated that he has changed the amount without mentioning it.

This months check was even less, back to the original too-low amount. I finally tell him (at 11:30 at night, probably sounding crabby) that it is hard for me to budget when I don’t know how much money I will be getting. At the first sign of what he perceives as questioning him or “conflict”, Donny flips out and says he could easily pay me more money but that he wants me to “work for it” by doing sales for him, which I’ve been clear from day 1 that I was 1) not good at and 2) not interested in doing or I would have pursued a sales career.

Then starts the classic rhetoric all single Moms hear: that I CHOSE to be a single parent and that I CHOSE to have a baby with that person, that my current situation is all my own doing. Followed by hinting that I am lazy and that I need to take “personal responsibility” for my predicament. He then drops a bomb by asking “how long am I going to do this?” I get mad and remind him that I was halfway through my degree which was PAID for and that I had wanted to finish, but that he was right, it was my fault that I had believed his promise to train me and give me work, which he not followed through on in 2 years. So now I have no money and no skills– nothing but some extra time to be a good parent to my daughter.

Then Donny says “I wanted you as a partner, but now Im not so sure,” which had failed to ever be mentioned to me. Apparently I had no say in that either. I got mad and told him not only do I not have time for any relationships, but that we have nothing in common, which we don’t- he voted for the One Who Is Not to be Named -not to mention a hearty “no thanks!” to all the boundary-crossing behaviors I put up with like never knocking but just walking into our house unannounced and at varying degrees of earliness to keep me guessing I guess. Locking the door makes him crabby. I have tolerated these behaviors because 25 years ago he emigrated from a culture where personal boundaries are not a priority, so I thought I was being understanding.

I have not heard from him in 6 days now when normally I get multiple texts per day. I assume he is pouting and will contact me with reasons why I am an ungrateful and overall crappy person. I actually feel enormous relief at not being scrutinized or controlled but am frightened for my financial situation.

What I want to know is: was it wrong of me to go along with this arrangement for so long? What if he contacts me and wants to continue this arrangement for more money? I intend to secure my own employment temping or something, but I am really regretful that I didn’t complete my education. Donny has been really generous, but at this point I feel so manipulated and disrespected that I don’t know if a can have any sort of friendship with him, whether he continues to pay me or not. He will see me as ungrateful and leaving because the money dried up.

I have been very appreciative and grateful and thank him constantly for his generosity, but it never seems to never be enough. He tells me I should just “be a good parent to my daughter,” which I am. I and my daughter make things for him and involve him with my daughters activities, but it’s still not enough. He is feeling under appreciated but doesn’t actually know what he wants. Donny has done a lot for us and I don’t think his behavior is conscious. I believe he is emotionally stunted for some reason. However, i cannot handle any more controlling and condescending bullshit. I am also aware that I am equally to blame for my situation. My motive was wanting to be able to be a good Mom for my daughter, no matter how short-lived. Finally, Donny was the only male figure in our lives my daughter could depend on, but I also don’t want to set a poor example by being manipulated and controlled by Donny.

Scripts for what to say to conflict- averse Donny if and when I hear from him would be greatly appreciated!

-Master Builder of Gilded Cages

she/her pronouns please, he/him for Donny

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hi captain,

i want to thank you so much for your website and lovely community and i hope this message finds you well. i’m having a hard time sorting through some relationship stuff and i’m hoping for some clarity.

i’m dating a very sweet and loving man who is still dealing every day with mental health issues due to early childhood trauma. these include ptsd, anxiety, depression (he is now in therapy for this) and nightmares. in his youth, he worked through his feelings of shame about what transpired in violent ways but that seems to be a thing of the past.

our courtship was fairly quick and we fell deeply in love, spending lots of our time together. in retrospect i should have been firmer about my need for a life and friendships outside of our relationship (especially at my age mid 20’s) but it all happened so fast. to be clear he does have friends/interests of his own but he is of the belief that our relationship is THE MOST important one in his life. he would be happy to rarely if ever spend time with anyone without/or other than me. in his words “i am the only thing that makes him happy” and “he welcomed dying before me but now wants to live as long as possible”. he constantly tells me i’m too good for him and is very insecure in our relationship. my friendships are deep and important to me and my feeling is that a romantic relationship should be something that adds to but is not the source of one’s happiness.

i was single for a long time before we met and had a very full life & was close with my family. they are thankfully still present but i spend much less time with them than i’d like because he doesn’t like last minute changes to our plans (even if those plans were netflix and pizza). i told him recently this needs to change and he agreed to work on it. because i’m the only thing that prevents him from having nightmares the idea of my being away causes him immense anxiety. sometimes i worry that he uses his trauma to manipulate me (his episodes early on often coincided with times i’d made plans with friends). we are also an interracial couple so that adds to a dynamic where anytime i express upset about his behavior or try to set a gentle boundary i am talked over, mansplained and/or the conversation is derailed due to the level of distress he’s displayed.

some of this is my fault as i’m not always good about expressing my feelings honestly and i want to hold space and be there for him. i tried to change parts of myself to make him more comfortable as he is an admittedly jealous person. i’m now doing my own work to come back to the vibrant, carefree woman i was when we met but it’s really difficult sometimes. i don’t know what to do or if the above is enough reason to leave or if i should keep showing up for myself, set clearer boundaries and love him through this.

any advice would be so appreciated,

sincerely,

trying not to be a pacifier

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Dear Captain Awkward,

I hope you’ll be able to help me out with this one, because it’s driving me batty. I suspect I already know what I should do, but wouldn’t mind confirmation.

To be succinct, my boyfriend who is learning to drive has a problem with receiving my criticism when he is driving my car. To the point where I do not want to say anything and want to just drive the car instead of giving him the experience.

Backstory: Boyfriend got his driver’s learner’s permit about 2 years ago (it’s at least a 2 – 5 year process where we live). He’s in his late 30’s, and he never got it before because he felt that he could walk everywhere, and, as he worded it, “Didn’t want the responsibility at the time.” Fast-forward to now, and he got the learner’s permit because he is realizing that in a rural area a car is a necessity.

I have had my full license since I was 18 (in my 40s now). I’ve owned multiple cars since then, and have paid for car insurance. Because of his type of learner’s permit, Boyfriend does not need to be on my insurance policy when he’s driving the car. He will pay for gas for the car, but that is about it for financial contributions.

When I was learning to drive on my parents’ cars, it was understood that driving was a privilege, not a right, and that if I adjusted the car for me, then I was to put it back as best as possible for either of my parents. When I ask my boyfriend to do something similar, I get pushback. Likewise, if my Dad told me to stop riding the white line, that was my cue to stop it immediately. I never gave them lip about it in return.

I don’t think I’m being unreasonable in my requests/critisms, but I’m at the point of stopping the driving training with him because it frustrates me and irritates me when he gives me this pushback about a request.

Am I being unreasonable? Any advice to try to stop the lessons?

Thanks,
Driving me crazy

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It’s that time of the month where we treat the search strings people typed in as actual questions.

Before I dive in: The trip to France was wonderful. We ate all the foods and saw all the arts and drove many kilometers and met lovely France-based Awkward folks who had excellent ice cream recommendations. I think it took Mr. Awkward a whole day before he was like “How do we move here forever?” and once he saw Lyon, where we tragically only had one day, he was actively in “No, seriously, let’s live here” mode. My favorite place we stayed is here. If you can go to Normandy, go, and let Vincent and Corinne envelop you in their hospitality and cook for you.

Came home to this:

onyou

The top half of my face visible above a black and white kitty stuck to my neck like velcro.

Sometimes it’s this:

onyou2

Same Jennifer, same black and white kitty, only this time I’m on my back and she’s on my shoulder/face.

As for this month’s theme song, I love Prince and I still feel his death last year pretty keenly. There was only one song this month could be:

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Hey Team Awkward,

This is a quick one. 

I’m newly sober and I’ve been attending AA for the last two months. One of my main meetings is a women’s meeting, which is rad, but I’ve tried to open it up a little bit–there’s a co-ed secular meeting and a co-ed meeting that does a physical outdoors excursion monthly. I’m getting a lot from all of them, and want to keep going!

That said, in less than three months, I’ve now had two different instances of what I’m pretty sure is thirteenth stepping (or a lead up to it). I’ve been dodging it, but I’d love some scripts for side-stepping being asked out, etc., without being alienating. I don’t think I’m being paranoid; I’ve been around the block enough time to discern the difference between A Dude Leaning In Too Much and a dude just being friendly. I don’t want to stop going to co-ed meetings, especially the activity ones. And I don’t want it to feel awkward.

So can you give me some scripts for turning down invites to go dancing, etc., or invitations of support that aren’t super alienating but make it a clear boundary? I’m good at “fuck you,” but not really good at enforcing this kind of boundary in a polite, peace-keeping way. 

Thanks in advance,
Awkward Alcoholic 

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Captain,

My partner (he/him pronouns) and I (she/her) have been together for 7 years and are getting married this summer. Our wedding will be a week away in a different state than we live, and we are so excited to spend the time with our family and friends. My partner’s sister is an alcoholic and drug addict with many coexisting conditions. She is abusive to my partner when she feels he isn’t “there for her,” and he went no-contact a while ago and told her to get sober if she wanted a relationship with him. She tried to kill herself on a camping trip with us one summer, and someone nearly drowned trying to save her. We cannot have her at the wedding. She is a danger to herself and others when alcohol is involved, and we do not trust her not to drink. She has made no efforts towards recovery and just last month got a DUI. She has been hospitalized multiple times in the last year on involuntary mental health holds, and was arrested for attacking a nurse. In our state, she has gotten off relatively easy. The state we plan to marry in is much less forgiving. If anything happened over the week the family is staying, she would be stuck very far from home and possibly imprisoned. She trashed her last apartment and was evicted, but was taken in by their mother. Due to her living with mom, we have seen her on rare occasion. At the last family gathering, she spoke as though she was coming to our wedding, and not wanting to rock the boat at their mother’s engagement dinner, we did not correct her. I feel some degree of manipulation is involved, as she was *not invited to the wedding*. Now we plan to write a letter to her laying out the reasons she can’t come along, but she will be crushed and angry. We intend to word it in the most respectful terms possible — on one hand we are dealing with a textbook addict, but on the other we have a family member with severe mental health issues that we want to be sensitive to. I am also afraid of the fallout. Mom wants to do a family sit-down and give it to her, but that seems cruel to me as there is nothing up for discussion. I would rather she process our decision on her own. How do we break it to her?

Signed,
Just want to relax during my wedding

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Dear Captain Awkward,

I’m a decade younger than my sister, who is in her mid-30s. After moving cross country, I feel so liberated and energized with the distance in place between me and my entire family.

I have played many roles for my sister…it was a draining pattern. Even as I have put distance between us, a good friend back home let me know my sister seems to have a new man in her life (spoiler: she doesn’t). How do I know she does not? With this latest new man, she’s forwarded me their exchanges. My sister is enthralled by striking up emotional affairs with male co-workers. She boasts how much these men reveal to her; how little they talk to their wives and girlfriends; or how these men don’t mention their wives/girlfriends to her. She’ll forward unsolicited text exchanges (I don’t want to see them, ever). The exchanges are basic who/what/where updates. She withholds communication (which is a relief, frankly) when I point out things like…ummm why should you know about their SOs in the first place? All of this strikes me as bananas. I work long hours in a male-dominated work place…I’m never privy to or pry for SO updates or information.

I’m at the point where I feel like I will lash out and say something that will really hurt my sister. Am I overreacting? Maybe this is an entertaining way to pass the hours while at work? Yet I want to broadcast: “Go pay for pricey therapy like I did! ” How do I communicate I’m no longer interested in hearing about her fantasy relationships and imaginary play-by-plays? Now I’m being judgmental, but I also think it’s sad to carry on a series of unfulfilling relationships. I don’t think there’s actually a way to help her, especially as I have spoon-fed her therapy resources and information, at her request. This was entertaining when, you know, I was in middle school and she was in college. She has never had a relationship and says she hates dating even though she was 18 when she went on her last date.

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