Guilty Single Moms Spending Trend ...

Lol, he's testing you and you are buying into it, literally too. Tell him he has to earn his money just like you do.

Probably many do. But I think it is coincidental to being single. I've seen it in 2 parent homes as well, more with daughters and moms than with sons and moms. It's something to look at and address, but I don't think it is "because" you are a single mom.

Start teaching him there's a difference between a need and a want.
I have three kids and I certainly don't go out and shop for them all fairly and equally at the same time. Except for Christmas and back to school they generally have different needs/wants at different times.
Also, your finances really aren't any of his business anyway. I wouldn't share so much information with him going forward. Even if he noticed your new shoes (which seems odd to me) how would he know they cost $50 unless you are telling him? I assume you don't have a joint account, and I assume he's not helping pay the bills, so like I said, not his business.

Like you said, "you just started a trend". Now you can stop it.
Just say "no, I'm buying shoes I need for me to wear to work. You don't
need any right now."
Just stop the automatic purchase w/yours.
Get him something when he does truly need it or for his birthday.
Stop the automatic expectation (or he might have a hard time adjusting to
the rules in the real world).
Most things that have been done (taught), can be "un-done". Most things.

I think that it's not just a single mom thing. I didn't grow up expecting that every time my mom got something, I did, too. It may have become the norm for him growing up, but you said he's a teen. You can say, "I'm only shopping for my work shoes today. You can look but I'm not buying. If you have your own money for your own purchase, that is fine." You can change this by simply not doing it. He may not like it, but he's old enough to 1. get a job and 2. understand that sometimes the trip isn't about him.

Does he have his own $50 to spend on the shoes? If so I would say let him go ahead and buy them, if not I would never allow my child to tell me that I had to buy him something because I bought myself something. I don't think it even matters that they were for work. You could go buy yourself a pair of shoes just because you like them. That is your right as the parent and person who earned the money. I have 4 kids and I would never buy all 4 of them shoes just because 1 child needed a pair. I probably spend more money on stuff for each 1 of my children then I ever do on myself but I buy stuff when I think it is needed or deserved not when they tell me I have to buy it.

I am not a single mother so I can't speak for how that would effect anything but I think you need to have a serious conversation with your son.

Time to admit to him and to yourself that you started something out of guilt and wish you hadn't. It has escalated into a sense of entitlement in his view, and that's not how the world works. You bought, essentially, a required work item - that doesn't mean he gets a treat just for having been born. If he's a teen, you can go shopping without him, but that doesn't address the issue of his view that there is money to go around and he's deserving. I agree that you can tell him you bought clothes when he outgrew them, but be sure he doesn't view that as permission to toss away his things so you buy more.

You could also total up, as one of many future life lessons, what things cost in your home: mortgage/rent, food, electric, phone, maintenance, school supplies, medical/dental, and so on. Ask him if he wants to pay half of everything. Then figure out the time you spend cooking, cleaning, doing laundry, etc.

I'm not sure only single parents engage in this - I think a lot of parents who don't feel they can spend as much time with their kids (due to work and other commitments) also "buy" some appreciation from their kids. You might get a book from the library that talks about ways to help introduce kids to adult responsibilities.

Parents & children don't get to do a 50-50 division of anything: finances, labor, responsibilities. Time to disavow your son of this and let him know that the fact that he feels entitled to 50% of every dollar says that he's still too young to have any decision-making role.

Good luck!

Good time to teach him there's a difference between fair and equal. Fair - you each get new shoes when you need them. Equal - since you only buy shoes for yourself once a year, he only gets a new pair of shoes once a year even if he's outgrown his old ones. Suddenly equal is not so enticing. Also good time to remind him that you worked for the money to pay for those shoes, he's welcome to earn/save his money if he wants new shoes he doesn't need.

Just say, 'no, not today. You don't need it, and I can't afford it.'

Works with my children.

learn to say NO its that simple-your the parent not the friend

Please re-read Mamazita's most excellent answer.

Mamazita, a bouquet to you!

No. Explain to him that when he was little he outgrew his clothes and you had to spend a lot more on his wardrobe than on yours. You could wear your clothes for years, he could only wear his for months. Now it's Mom's turn to have new things.

There's this wonderful word: "No."

Thanks for your honesty. I was a single mom for a while. Lots of bad habits happened at that time. When I remarried, my new husband questioned things. I saw his side. He was a wonderful step dad so I knew it was not a jealousy deal, I was just too caught up in my 'guilt' to see the whole picture. Put a stop to it. Good luck.

I just teach my kids that we buy things because we need them, not because we want them.

I really don't think this goes for just single moms. I'm married and my now 26 year old used to be this way and my 9 year old triplets used to be this way until I put my foot down and let them know that I am the parent and hardly spends a thing for myself so suck it up if I come home with something for ME! It may be a habit you got into where he thinks of himself as a type of equal but you need to put your foot down and explain the way things need to be from now whether he likes it or not as he's the child and you are the parent and the bread winner, period. He can always get a job and earn money. Change the trend before it gets even more out of hand.

K. B
mom to 5 including triplets

I never insituted a "fairness" policy regarding spending. She got what she needed when she needed it, and I got what I needed when I needed it. I didn't buy her a new pair of shoes every time I bought myself one, any more than I bought her a car when mine died and I had to replace it.

We buy something when we need it.
If he's outgrown or worn out shoes/clothes then we shop for them.
Our son doesn't get things every time I go shopping - and I don't always get something for me if I get something for him.

Exactly what Mamazita said.

It's got nothing to do with you being a single parent, it has to do with how things have been run. My kids get frustrated when I spend $ on myself sometimes, but when I look at them, they know to zip it. It's not about being fair. I have lost a lot of weight in the past year and a half and I need things that fit. When they need things they get them as well. Rarely do we do WANTS.