A
female
age
36-40,
anonymous
writes:I know some of you may find this question a bit ridiculous, but it's been driving me mad!My 27 year old boyfriend has never bought his own underwear. His mother buys them. She sends him boxers for every holiday. He has Halloween boxers, Christmas boxers, Valentine's Day boxers, 4th of July boxers, etc. I feel that he is too old for this!!! It appears as though she has no plan in stopping, so am I supposed to accept this when he is well into his 30's????I've tried to drop hints that it's weird by playfully telling him he is too old for it, but it doesn't phase him one bit. How do I seriously confront him about this without hurting his feelings? S
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reader, anonymous, writes (24 April 2012): Don't let what other people are saying confuse you. It's very weird. People who find it okay for parents to be buying potential sex clothes normal might have some issues to work out, not to mention a lack of empathy for you in this situation.
How is a girl supposed to go down on her man when the last thing she sees before getting to her goal is a perfectly sized pair of boxers lovingly encasing his manhood purchased by mommy? Mommy thoughts shouldn't be a part of a healthy sex life and it can be a problem to be focused on the act when confronted with a small reminder of Mommy right before the last barrier to intimacy is removed.
Does your daddy buy you underwear for every holiday? If he did, I bet people would think that it was weird and a little f***ed up. I bet most people would think it weird that your mother bought you panties every valentines day as well.
A mother purchasing her adult children underwear is not in a healthy mind set. Sure sure "you will always be my little boy" is what is going through their head... But they are not little boys anymore. They are not doing little boy things with their underwear anymore. The penis that is being protected by the cloth chastity belt is not a little boy penis anymore.
Mommy's shouldn't have anything to do with their adult son's genitals or the clothing articles that keep those genitals comfortable throughout the day.
Have her buy a t-shirt, a cap, socks, a card, a box of holiday candies... There are plenty of options out there to keep the "tradition" without involving his sexual organs or potentially interfering with your sex lives.
"Awesome! We cant wait to break these bad boys in! Next year you will have to buy us a couples set so we can really make a night of it!" - Perfect way to say thank you to underwear gifts.
Personally, I think the only time outsiders should be buying underwear is the bachelorette/ bachelor party. Even then, you're probably better off returning them and picking out your own.
A
male
reader, anonymous, writes (28 February 2012): Huh? You called that weird? My mom buys my underwear every year up until I was about 30 years old. No, she didn't stop buying because I turned 30. I happened to buy some myself and I let her know. She still buys me some when she has a chance. I'm not a mama boy. I have a respectable job with a nice house, drive luxury car that I bought by myself. It's just a bond between mother and son. There is nothing weird about it. She's HIS MOTHER.
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reader, anonymous, writes (26 February 2012): "I guess it's a good thing I'm not dating you, huh?"
Damn straight. I'd rather a girlfriend and not a patronizing second mother.
"My babe's growing up! lol."
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reader, anonymous, writes (26 February 2012): This is verified as being by the original poster of the questionThanks for all the responses guys!Like I said before, my opinion is my opinion, that isn't going to change but it's cool to hear everyone's POV!I discussed it with him last night and it went great! He actually agreed that he has become so accustomed to wearing the boxers his mom buys him, he just never made the effort to start purchasing his own! He even bought his very first pair of grown up boxers today while we were out! :) My babe's growing up! lol.Cerberus, I think you put a little too much thought into this and totally overanalyzed the situation...."I can't see anything else here that would lead me to continue a relationship with a girl like you in that circumstance." --well, I guess it's a good thing I'm not dating you, huh?...lol"By taking away their traditions you seek to become the most important woman in his life and obviously see his mother as a some kind of threat." ---This is just nonsense. You really shouldn't come to such conclusions when you know absolutely nothing about our history/relationships with one another.Night everyone! :)
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reader, anonymous, writes (25 February 2012): OP as someone previously stated you have to learn to pick your battles.
Is underwear really a good reason to insult him, insult his mother and impose your standards on him?
You may find it weird but as you can see the vast majority of us think you're the one who is weird for making an issue out of this.
You basically sound to me like you're trying to manipulate and control him on a very minor issue. You want to change a tradition he and his mom have of exchanging gifts because you find it weird.
I can't see anything else here that would lead me to continue a relationship with a girl like you in that circumstance. I would be very insulted if my girlfriend tried to interfere in my relationship with my mother, tried to tell me that my very common and acceptable show of love and affection with her in such a minor but significant way was somehow weird. I'd choose my mother over my girlfriend every single time, there really is no contest and I definitely wouldn't accept any woman (or male friend) trying to impose their values on me especially on something that most people not only are okay with but most think it's cute.
Would people think it weird if your father bought you underwear? That's not done really is it? Fathers have no idea of their daughters measurements and don't really want to know that either. You can't impose a father's relationship with his daughter onto a mother/son relationship, they're completely different.
Something tells me this is more than just about underwear OP, it seems to me like you're trying to dilute the relationship and bond he has with his mother. By taking away their traditions you seek to become the most important woman in his life and obviously see his mother as a some kind of threat.
You see there are lots of things our partners do that we either don't like or find strange because it's not in our tradition. I had an ex that was very physically affectionate with her father. A grown woman who would still sit on his lap while he stroked her hair. They held hands and all that kind of thing. Strange to me yes, would I dare try and convince her that she shouldn't do that any more because I thought it was weird? Not at all, not only do I not have a right to insult the traditions and bond she has with her father but who do you think would win in that circumstance?
It's who she is, it's the bond she had with him and it was up to me to either accept her as she is and the things she likes to do or move on. A person who would try and change another over feeling weirded out by a tradition or custom that's not actually weird is domineering, controlling and manipulative. This isn't a harmful thing, it's not like he's not brushing his teeth or that he's risking his health by smoking, it's a cute little custom with his mother and there is no way you can approach this with him without hurting his feelings. I think everyone here has told you that.
As another poster stated if you don't like the types of underwear then get him some good quality, calvin klein boxers. Get him boxers that are more comfortable than the tacky ones with rudolf or love hearts on them and he'll be more inclined to wear them, find that too weird? Then either get over it or create a massive problem out of nothing.
Because OP the fact that he gets his underwear bought from him is nowhere near as important as what it symbolizes because of who its from. Most of us guys get very defensive when it comes to our mothers do you really want to open a can of worms like this and alienate his mother?
Because if she suddenly decides she doesn't like you, or that you're trying to encroach on her relationship with her son, then ask any of the mothers here how they would react to a woman acting that way. It wouldn't be pretty.
I suggest you get over it, this is literally your problem not his and not his mothers they don't have to change their relationship to suit you.
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female
reader, chigirl  +, writes (25 February 2012):
 And may I add, off course there's going to be penguins with santa hats on his boxers, because his mother bought them. She's not going to buy him underwear that has any sexual denotation to it!
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female
reader, chigirl +, writes (25 February 2012):
I agree with Cindy, if you absolutely hate the underwear his mother buys him (and there is nothing you can or should do about his mother buying him underwear) then by him underwear yourself! Buy him a dozen of boxers you find sexy and then ask him to wear them when he meets up with you. Problem fixed. And his next girlfriend will get to see him in those boxers as well, but will probably never know who bought them for him.
It is controlling behaviour to tell someone how to dress, what gifts they can accept and not, and it is right out mean to call someone, who you supposedly love, weird. So there should be no confrontation here. Just laugh the matter off and buy him your own underwear if the penguins freak you out.
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female
reader, CindyCares  +, writes (25 February 2012):
 The answer was implied in our posts. Since most of us don't think it is weird, in fact it is rather common, then there isn't a good way to "confront " him without hurting his feelings, because that would imply that HE is a weirdo, or a mama's boy,or that HIS MOM is a weirdo. Rather heavy critiques, coming from a gf. You also risk that , rather then feeling hurt, he would see you as territorial, bossy, or controlling ,as if you demand the right of approval on what gifts he can receive from whom . After all, you would not " confront " him for eating a cake baked for him by his mother- even if at 27 he can surely cook or buy his own cake ; if you would, he'd be justified in taking offence.
Perhaps you can tell him that you find the funny boxers very unsexy ( who could blame you,lol ) and they turn you off, and what turn on would be instead seeing him wearing something more manly . And YOU could go buy him half a dozen of cool, stylish underwear , so he would wear yours even if the penguins should keep coming.
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female
reader, tennisstar88 +, writes (25 February 2012):
 You could say, "Don't you think you're a bit too old to be wearing those penguin boxers?". Although, if your comments haven't phased him...then you're going to need to be completely honest, even if that means hurting his feelings.
However, I highly doubt he's going to tell his mom to stop buying boxers for him. And I'm sure she's not going to stop buying him boxers either. Are you going to tell her to stop? She's definitely not going to listen.
Really, I wouldn't say anything because it will fall on deaf ears all the way around. Not to mention it's an incredibly stupid to make a big deal over nothing. So, I'd deal with his flamingo print boxers.
His mother buys them for him, he likes wearing them. Who are you to tell him how to dress?
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female
reader, Miamine  +, writes (25 February 2012):
 Sorry that we are different from you and find your guys behaviour normal. Can't tell you how to confront him because the guys I know would find you strange and confrontational.
Best way to get round this, is to clear out all his underwear and hide them and replace them with one's you buy yourself, one's you like a lot better. Just tell him "surprise baby, I want you to wear these for me from now on".. Don't tell his mother what to buy for her son or how to treat him, that may create unnecessary friction.
I don't think the guy cares who buys his stuff, as long as he's got some. He would probably rather do something else than pick out underwear. Your underwear, mum's underwear, he doesn't care and that's why he wears penguins.
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female
reader, Aunty BimBim  +, writes (25 February 2012):
 I find your fixation on who buys his underwear a little weird, does he care his boxers have penguins, or halloween themes? I doubt it, otherwise he wouldn't be wearing them.
What is it you object to here, the fact his mother buys his boxers, or the fact she buys him funny boxers, or the fact he wears boxers purchsed by his mother, or the fact he wears funny boxers, or the fact you believe his boxers are childish and the fact they are purchased for him by his mother demostrates quite graphically he was loved by another woman before he met you and still is?
You need to work out why this bothers you so much, and what aspect it is that you want to CONFRONT him over. Confront is a rather agressive word, why did you chose that word? What the hell is there in this situation that calls for CONFRONTATION anyway?
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reader, anonymous, writes (25 February 2012): This is verified as being by the original poster of the questionMy question was not whether or not you guys think it's weird, my question was how to confront him without hurting his feelings.
I see that a lot of the men here still have their moms buying them underwear...well guess what? I still think it's weird. There comes a certain age where it's a bit ridiculous. I'm sure you would think it's weird if my father bought me underwear at the age of 30, right?
Anyway, maybe the situation would be a little better if she bought him GROWN UP underwear, not boxers with penguins wearing santa hats.
...and calm down Cerberus. My opinion does not make me childish or immature...there's no need to curse. But thanks for the response!
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female
reader, Miamine +, writes (24 February 2012):
I'm another one who doesn't know many men who buy their own underwear. All the men in our family get underwear, handkerchief's, aftershave or ties. The lucky one's might get a bottle of whisky. Not sure what else to buy them, so that's what they get, every Christmas, every Birthday from every woman they know. I think girlfriends probably try harder though. And maybe mums and grandma might give money if they think their son's are desperate, or jumpers if they like knitting.
This is not unusual in my world. Poor men.
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female
reader, chigirl +, writes (24 February 2012):
My last boyfriend's nicest pair of underwear (and newest as well), which were my favourites, were from his sister! He got them for christmas. I wish she bought him more underwear, because everything else he had was worn down and ugly. And these had cute reindeers on them, awww....!
It's a completely different thing buying underwear for guys, and underwear for girls. Buying them for guys is acceptable and ok. It's just boxers, small medium or large, and you pick a fancy colour or fun motive. It's like t-shirts. For women on the other hand... we got thongs and tangas and girl boxers and panties and french openings, hold in's and lace, cotton mix, micra and silk etc. It's a jungle, it's private, and the sizes are a secret.
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reader, anonymous, writes (24 February 2012): My Dad is one of those Jock, INDEPENDANT, ALPHA MALE, types. So he was buying his undies with his own hard earned cash at age 14. He also bought his own bike then too. His advice, that is very odd for a guy to not want to be his own man.
Christmas, its okay to get socks for Christmas. Underwear are for the Wife or GF to buy along with him getting his own underwear.
Dump him and date a REAL man. :P
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reader, anonymous, writes (24 February 2012): "Nothing weird about it, its not like his mothers buying him sexy underwear or anything."
Haha, imagine that? Opening your gift from your mom at xmas, at home in front of all the family and it's a leather, studded thong or something. That would be hilarious and very awkward.
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male
reader, anonymous, writes (24 February 2012): My mum still buys me 3 new pairs of underwear every christmas and I'm 29. I have to make sure she keeps the receipt as she always gets the wrong one lol! Nothing strange about it, ask any guy what they got for christmas and pants and socks are common on the list of answers. Its practical and most guys appreciate it. Mums are just funny about wanting to buy things like that. I appreciate it more than some pointless mug or a dvd I'll only watch once and more than likely already seen. Nothing weird about it, its not like his mothers buying him sexy underwear or anything.
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reader, anonymous, writes (24 February 2012): I haven't bought underwear nor socks in over ten years. My mother and my girlfriends buy those for me as gifts so why would I bother?
I currently have 14 pairs of underwear. I can go two weeks without having to wash them if needs be. Underwear lasts about a year. I get them as gifts every valentines, my birthday, xmas etc. I get on average 14 new pairs of underwear and tonnes of pairs of socks every year. Take into account the fact that rotation means I only ever wear the same pair of underwear once every two weeks/26 times before I throw them out then what need do I have to buy any?
Believe it or not OP underwear is one of the best gifts you can get a guy. They're the most important piece of clothing and there is no better feeling than a putting on a new fresh pair of underwear. My mother and girlfriend know which ones I prefer, the ones that are the most comfortable and I've taken it for granted that they'll get me more.
What's wrong with that?
You're the one who's being childish and immature here OP. it's just underwear for fucks sake. Surely your mother buys you gifts she knows you like right? Would you give those back just because you're able to buy your own or he somehow thought you should be "old enough" to buy your own.
That's stupid as hell.
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female
reader, CindyCares +, writes (24 February 2012):
She's not " buying him underwear ", she's sending him gifts.For Xmas, Valentine, other special occasions.
What's so strange about that ? My sister often bought me panties and bras for bdays or Xmas, I never saw it as if she is picking my underwear for me.
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female
reader, Ciar  +, writes (24 February 2012):
 I think it's fairly common for mother's to buy their sons underwear. My mother in law did it at Christmas and I've heard of others doing it.
Why is this a problem for you? How exactly does it affect your life?
Defiitely pick your battles.
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female
reader, Beaniepants +, writes (24 February 2012):
 If there is one thing I've learned in relationships: pick your battles. Honestly, this should just end up being an inside joke and some chuckles with you two.
You didn't say anything else strikes you weird in their relationship? My mom babies my 25 year old brother to no end...its' a family joke now!! She sends him underwear too...and his favorite mexican food burritos fed ex on dry-ice at least three times a year.
Don't be at odds with who could be your future mom-in-law over this.
Pick your battles!! :o)
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female
reader, Anonymous 123 +, writes (24 February 2012):
 There's nothing weird about it.
I think there is a fairly large percentage of men whose underwear is still bought by their mothers or wives, they've probably never bought it themselves. My brother's underwear is still almost always bought by either me or my mom. Its not weird, because that's the way its always been. When he was younger he has horribly embarrassed about buying his own underwear, so we would buy them for him, and now that he's a big boy, I guess its more a matter of convenience than embarrassment. Like Chigirl said, my brother too is lousy at shopping and its just easier when me or my mum buy it for him because we know what he wants.
I dont think you should make a big deal out of this. He likes it and he doesnt have a problem with it. Why is buying underwear any different from buying a shirt anyway? She's his mum, she knows what he likes and wants and its something that she's always done, so there's nothing wrong with that.
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reader, anonymous, writes (23 February 2012): Fricken toss them out and buy him some tighty whities.
Its weird in that its a shared pattern of behaviour of Mommy's boys or emotional incest relationships, which is unhealthy, between a man and his Mother.
There is a fine line between respectful, loving, honouring a Mom and then this type of dynamic.
MOST 30 year old men prefer to be in control of such matters and prefer to be independant.
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female
reader, Aunty BimBim +, writes (23 February 2012):
You don't say why you think this is weird. Just because your mother doesn't buy you underwear doesn't make his mother buying him underwear weird.
She's his mother, there is nothing weird here at all and I don't see it any different to her buying him t shirts or knitting him sweaters.
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female
reader, chigirl +, writes (23 February 2012):
It's gifts, Let his mother buy him gifts, thats on her. She can give him what he wants, and he can't be held responsible for her actions.
However, you can tell him you think the boxers make him look geeky or like a kid, or that they aren't sexy, and then ask him if he can't buy his own underwear to wear when he meets up with you.
I buy my brother underwear sometimes. Not because he can't buy it himself, but because it's an ok gift when Im out of ideas and he's lousy at doing shopping so he always needs boxers and socks. It's just a safe bet to get a guy.
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