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Dear Sugar Mama

Your money questions, answered by Haley. Debt, love, family, inheritance, all of it.

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Volume 81Love & money

How do we split a trip when one friend makes less?

Dear Sugar Mama,

I’m in a bit of a predicament. Three girlfriends and I are planning a holiday trip together. We all decided to forego family obligations this year and go somewhere fun. I’m soooo excited BUT there’s been a hold up. One of my girlfriends makes significantly less than the other three of us. She doesn’t have the budget for some of the hotels we want to stay at in Rome, has made comments about the dinner reservation being pricey, and it’s starting to create some friction. I am totally down to help cover and offset some of her costs so we can experience the trip the way we want but how do we handle…

Signed, Splitting the Check in Rome

Haley writes back“And may I just say Rome for the holidays sounds like the dream.”

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Volume 75Career

I just got laid off. Now what?

Dear Sugar Mama,

After 8 years of employment at my dream job, I was part of a mass layoff yesterday. I am very concerned about how I will be able to pay my bills without depleting my savings until I find another job. I'm single, own my own home, and have 2 months salary in savings. I also have a large student loan debt. How do I manage my financial responsibilities without incurring more debt?

Signed, Ms. Between Chapters

Haley writes back“Ahhhh I'm so, so sorry about the job loss!”

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Volume 55Saving

How do I stop raiding my emergency fund?

Dear Sugar Mama,

I keep sabotaging my own savings. I had a solid emergency fund. Then life happened (school, moves, trips, etc), and now every time I rebuild it, I end up spending it again. When I see money sitting there, my brain treats it like money I’m allowed to use because I assume I’ll “fix it later.” I know that defeats the entire point of an emergency fund, but I can’t seem to break the habit. How do I rebuild my savings from almost zero and actually leave it alone? Should I make the money harder to access so I'm not constantly tempting myself?

Signed, Trying Really Hard to be Responsible

Haley writes back“Right now, you’re treating your emergency fund like a situationship.”

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Volume 56Family

How do I plan to become a single mom by choice?

Dear Sugar Mama,

I'm 41, single, tired of swiping on Hinge, and seriously considering becoming a parent on my own using IVF and donor sperm. Having a child has always been part of my life plan, and emotionally, I feel ready. (I froze my eggs a couple years ago.) Financially, though, I'm spiraling. I earn $170k in a stable senior role, have no debt, about $250k in retirement savings, and $15k in cash. I rent in a high-cost city, and after covering my monthly expenses I only have about $750 left over, which feels nowhere near enough to cover childcare and everything else…

Signed, Single Mom in the Making

Haley writes back“First, I want you to know this is not delusional.”

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Volume 57Family

Starting over as a single mom after divorce.

Dear Sugar Mama,

Where do I even start. Early 2024, I find out my husband is having an affair. Devastating, obviously. Except I was five months pregnant when I found out. I'll spare you the chaos that followed. Just know it was a lot, and I got through it. What actually didn't fall apart was my divorce settlement. So there's that. Now I'm a single mom in my thirties raising the most incredible little girl and trying to figure out my next moves. I refused to be made a fool of twice. Here's where I'm at: Almost $90K in savings (still sitting in a regular savings account,…

Signed, Shrewd Single Mom (NOT An Alimony Pony)

Haley writes back“First of all, NOT AN ALIMONY PONY might be the best sign-off this column has ever received.”

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Volume 58Debt

Do I pay off my loans or buy the Chanel?

Dear Sugar Mama,

I think Chanel is psychologically torturing me and I need help. Fashion isn't just a hobby for me. It's literally who I am. And there's this new Chanel era happening right now and all I want is to be part of it. But then I open my bank account and it's like. oh. student loans still very much there. IRA completely empty. and I'm just standing here cosplaying a financially stable person. My TikTok is not helping. one video it's a $10k unboxing, the next it's "we're heading into a recession" and "AI is coming for your job." I genuinely don't know how to…

Signed, Chanel Dreams, Student Loan Reality

Haley writes back“Can I just say we have had some EPIC sign-offs the last few submissions of DSM- Chanel Dreams, Student Loan Reality is sending me.”

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Volume 59Saving

How do I plan my money when I'm still waiting on a partner?

Dear Sugar Mama,

I'm 37. I work in tech, I'm climbing fast, I make good money, and I froze my eggs two years ago so I'm not in full panic mode on that front. By every metric I'm doing really well. and I know that. But……I want a partner. Like I really want one. And I haven't met him yet. And some days that feels totally fine, and some days it feels like this giant question mark hovering over every financial decision I make. Do I buy a place alone? Do I keep renting cause what if I meet someone in another city? Do I max out my retirement like a true single person or do I…

Signed, Financially Together, Personally Still Waiting

Haley writes back“First of all…ARE YOU ME?!!!”

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Volume 60Family

Should we lend my sister-in-law $25,000?

Dear Sugar Mama,

My husband and I have done everything right - house deposit saved, emergency fund solid, investments growing, baby we're obsessed with. We're not rich, but we're not stressed. We built something stable, and we're proud of it. Then his sister called. $25,000 in credit card debt. A gambling addiction that's spiraling. A family watching her fall apart in real time. My husband and I are a united front on wanting to help. But here's what's keeping me up at night: we've been talking about offering her an interest-free loan to wipe the debt and give her a…

Signed, Cautiously Compassionate

Haley writes back“Before we even get into the money stuff: you are a good person for even considering this.”

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Volume 61Love & money

My boyfriend spends everything he makes.

Dear Sugar Mama,

I have been with my boyfriend for two years and I love him but I am starting to panic about our financial incompatibility. I am extremely frugal. I max out my Roth IRA every year, I have six months of expenses saved and I genuinely get so excited about a good deal lol. He is not like this at all. He makes more money than me, has almost nothing saved and spends so freely on things that feel completely unnecessary to me. He is not in debt and he pays his bills but the idea of saving for the future just does not register for him. We have started talking…

Signed, Frugal and Freaking Out

Haley writes back“You are not overreacting.”

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Volume 62Saving

How do I go from getting by to getting set up?

Dear Sugar Mama,

I am 28, making low six figures, renting, paying my bills on time and carrying only $15k in student debt and a small car loan. On paper I know I am doing well, especially for my 20s with no kids and a salary my parents would have killed for at my age. But I do not feel like I am building wealth. I am trying to be responsible and set myself up for the future but it feels like everyone around me, who I am pretty confident are in the same financial boat, is jetting off to Europe twice a year while I am over here trying to figure out how they can afford…

Signed, Trying My Best, Still Stressed

Haley writes back“First of all you are not behind.”

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Volume 63Inheritance

My grandmother left me more than my sister.

Dear Sugar Mama,

My grandmother passed away three months ago and left me significantly more than my sister in her will. We are talking a $200,000 difference. My sister does not know the exact number yet but she knows we did not get the same amount and she is not handling it well. She has started making comments about how I was always the favorite, has been distant and recently told our mom she thinks I should split it with her equally. I love my sister but I do not think I should have to give away money that was left to me by someone who made a very deliberate choice. I…

Signed, Grateful, Guilty and Slightly Scared of My Sister

Haley writes back“First of all I am so sorry for the loss of your grandmother.”

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Volume 64Career

Should I quit my job without something lined up?

Dear Sugar Mama,

I am, as the kids say, having a full crash out over my job and I need someone to talk me off a ledge or push me off it. After six years at my company, through Covid, layoffs, industry chaos and more restructures than I can count, I am at my absolute breaking point. The Q word has been thrown around. Loudly. Without a backup plan in sight. Here is the situation. I have been passively looking for a year and actively looking for five months, complete with a career coach, hundreds of applications and exactly one interview. One. A recruiter told me she…

Signed, Defeated Corporate Girly

Haley writes back“First of all a pension in 2026 is basically a mythological creature.”

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Volume 65Love & money

My boyfriend bets $100 a day on sports.

Dear Sugar Mama,

So the Knicks won the championship last night and my apartment is still recovering from how loud my boyfriend was. Which brings me to my actual problem. A few weeks ago I found out he has been sports betting. He swears he has it under control and has set himself a strict limit of $100 a day. On one hand I appreciate that he set a boundary. On the other hand $100 a day is $700 a week and $3,000 a month and that math is making me deeply nervous. He says it makes watching games more fun and that he is being responsible about it. I do not want to be…

Signed, Worried in the Stands

Haley writes back“First, congratulations to your boyfriend and to the entire city of New York because the Knicks winning their first title in over 50 years…”

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Volume 66Love & money

How do I date without going broke?

Dear Sugar Mama,

So I know this is probably not your typical submission. straight guy here. I found your newsletter through a girl I was dating (she ended things, I kept the newsletter subscription haha. felt like the right call.) Anyway I need help. Dating in New York City is making me broke. I looked at my credit card statement last month and lost my shit. I'm 31, make good money, have my 401K sorted, no real debt. I'm not an idiot with money. But between the dinners and the drinks and the Ubers I genuinely don't know where it's all going. It just disappears. I'm not…

Signed, Broke But Make It Romantic

Haley writes back“You kept the newsletter after the breakup.”

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Volume 67Love & money

My fiancé won't talk about money.

Dear Sugar Mama,

I love my fiancé. Truly. He is SO kind, he makes me laugh, he shows up for me in every way that matters. But..we cannot talk about money. Every time I try to bring it up, whether it is a budget, our savings, what we each make, what we owe, he shuts down, gets defensive, and/or changes the subject. I still do not actually know his salary. I do not know if he has debt. I found out recently ( by accident) that he has a credit card I did not know about. We are getting married in eight months and I am starting to panic a little because I am marrying someone…

Signed, In Love and In The Dark

Haley writes back“You are not overreacting.”

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Volume 68Family

How do I save for my kids without hurting financial aid?

Dear Sugar Mama,

HELP! I thought I had done my due diligence and built a solid financial plan for our family... but the more I learn about money, the more I realize there's an entirely new thing to worry about every Tuesday. My husband and I are in our late 30s. We're living comfortably, but we're still paying off our own student loans, saving for retirement, and raising two young kids. We both came from modest means and are trying to give our children a better financial head start than we had. Here's what we've done so far: I opened 529s for both kids. Our state offers…

Signed, Raising Rich Kids

Haley writes back“Ok first I need you to step away from Google.”

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Volume 69Saving

What should I do with the money coming in right now?

Dear Sugar Mama,

I've been reading your newsletters for a while now and they are truly the ONLY newsletter I don't skim, or delete altogether without opening. I'm a 33 year old that just found herself back in my BFE hometown (breakup, needed to reset my nervous system) after 10 years in LA and New York City hustling and building my brand. There is so much noise around financial stability and comparison. I mean my mom had an established career, was a homeowner (!), and pregnant with me around this time and I am literally living with family and cannot even fathom…

Signed, Confused and Overwhelmed Milennial

Haley writes back“First, LOL to BFE hometown.”

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Volume 70Investing

I'm in my forties. Where do I start?

Dear Sugar Mama,

I'm in my forties, married with kids, and I've been working a full time since I graduated college about 20 years ago. Most of the places I've worked I've contributed to a 401k. I'm so embarrassed to say that I truly don't understand it and have never educated myself on what I should be doing. I've moved around to a few different jobs over the years and have just let the money sit in various accounts. I think I've been avoiding this since I'm so embarrassed that I don't know where my money is. I want to get things on track and just need some guidance on…

Signed, Future Rich Person (I hope)

Haley writes back“Let's get one thing straight - you are already a Future Rich Person!!”

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Volume 71Love & money

I make more than my partner. How should we split things?

Dear Sugar Mama,

I saw your video about Jennifer Aniston and her boyfriend and it sent me down a rabbit hole bc it actually contradicts a lot of what the Hormozis teach about holding your partner financially accountable. And I found myself somewhere in the middle of both of those ideologies and honestly a little confused. Here's my situation. I make significantly more than my partner. But we genuinely work as a team - he makes me breakfast and dinner every day, handles the laundry, takes care of our cats, and keeps our home running. So I cover a bigger share of the…

Signed, Breadwinner, Baby Planner, and a Little Bit Stressed

Haley writes back“First of all, thank you for sending this in!!”

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Volume 72Saving

How do I build wealth when my balance hits single digits?

Dear Sugar Mama,

I love your advice, and I've learned so much from you, but I'm struggling with a bit of a disconnect. I feel like most of the financial advice out there assumes a lot about the level of income of the consumer. I'm in my late 30s. My passion is in the animal welfare field, and I'm currently working at a shelter making $19 an hour. I live in a big city, which means everything is expensive. I also have accumulated tens of thousands in debt from various sources including student loans for master's degree that I'm halfway done with. I have absolutely nothing…

Signed, Starting From the Bottom

Haley writes back“First of all, you are right - thank you for writing in.”

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Volume 73Career

Why do I feel ungrateful asking for a raise?

Dear Sugar Mama,

Ok I need help with something that I KNOW is irrational but knowing that doesn't seem to make it go away. Every time I think about asking for a raise, negotiating a signing bonus, or even bringing up education reimbursement I get this overwhelming feeling that I'm being ungrateful. Like who am I to ask for more when I already have a job I like and people who want me there? The opportunity itself should be enough right??? And I know I KNOW that this is internalized misogyny talking. I know men don't sit around feeling guilty for negotiating. I know the…

Signed, A Short Queen Selling Herself Short

Haley writes back“First of all…WOW - did you come up with your sign off name?”

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Volume 74Career

Is my comfortable day job still worth it?

Dear Sugar Mama,

I'm in my late 30s, married, and have two young children. I'm currently still pursuing my dream career of being an actor, and while I've had some success, I haven't reached where I want to be. I currently have a full time day job at the same company I've worked at for the past 15 years (...so, can it really be considered a "day job" anymore??). The reason I've stayed with this job is because it's fully remote, fairly flexible, and not stressful. It's a job that doesn't "take" from me emotionally or mentally. BUT the salary is modest and we are…

Signed, Waiting in the Wings

Haley writes back“So before we get into the money I wanna say one thing right at the top - 15 years at the same company does not HAVE TO mean 15 more.”

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Volume 76Investing

Should I be worried about AI and my investments?

Dear Sugar Mama,

After all of the AI craziness in the news this week should we be worried about our investments? Is there a possibility that AI will somehow hack into the market systems and crash everything? I would love to buy a house in the next 5-7 years (currently single with no prospects so need to plan for it as if I am on my own…). I have more in savings than a 6 month emergency fund. I know that if I have a dream to own a house, I really should be investing the extra. Especially, as I currently only have a fairly small amount in investments at the moment. I’m…

Signed, New-to-Finances-and-Scared!

Haley writes back“Just want to validate that the news around AI has been A LOT lately.”

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Volume 77Debt

What do I do when bankruptcy feels like the only option?

Dear Sugar Mama,

I'm in a real pickle. Since COVID, I have been laid off three times. Because of that, I had to use most of my meager savings (Millennial, entered the workforce at a tough time, my entire life has been a crisis, etc.) and relied on my credit cards more than I normally would. As a result, I now have almost $10K in high-interest credit card debt and minimal savings (it's in a HYSA, don't worry!). After the three layoffs, I couldn't get hired in my field for 11 months, so I changed industries and got a totally different job, which meant an entry-level…

Signed, Average Exhausted Milennial

Haley writes back“Wish I could reach through this computer screen right now and give you a huge hug.”

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Volume 78Debt

Can I pay off debt and save at the same time?

Dear Sugar Mama,

Is it possible to pay off debt and build savings at the same time? Here's the sitch: I'm 28 and making decent money in the Northeast. I have a cushy marketing job, and even have built a side hustle that's consulting for businesses in my city who need a little extra marketing support. Personally, I am in a committed relationship, and starting to talk about taking next steps with BF/fiancee-to-be. We're getting excited about getting engaged, planning a wedding, buying a house, and all the things that come with building your life with someone. The twist…

Signed, Formerly Irresponsible, Presently Confused

Haley writes back“Ok I know you think 22 year old you was irresponsible, but I DO NOT see it this way!”

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Volume 79Love & money

What should we talk about before getting engaged?

Dear Sugar Mama,

I am in the happiest, most respectful relationship of my entire life. We just moved in together and are talking about getting engaged later this year. We both are ambitious and have big dreams of what we'd like to accomplish - together! I am thrilled about our shared future and would like to be responsible in preparing for the financial aspect of marriage. As they say, marriage is the biggest business decision you can make. Two requests for Sugar Mama: Is there a check list of financial topics you recommend discussing as a couple before getting engaged?…

Signed, Soon-To-Be Financially Flummoxed Fiancé

Haley writes back“Congratulations on finding your person AND (kinda even bigger congrats) for having the self awareness to think about this stuff before the…”

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Volume 80Inheritance

Where do I find advisors I can trust?

Dear Sugar Mama,

My father recently passed away after a difficult battle with cancer. I am his only child and after divorcing my mom he never remarried. He was also two years away from retirement age, which means he worked and saved for a retirement he did not get to enjoy. The silver lining in this terribly depressing grey cloud is that I am the beneficiary of these funds, which is now helping my husband and I to be in an amazing financial place for our current and future selves. I know he saw this as a final gift he could give to us and I am doing my best to shift my…

Signed, Daughter Trying to Do Her Best

Haley writes back“I just want to say first I am so, so sorry for your loss.”

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