rSlash - r/Bestof I'm 19 and Dating a 40-year-old MILF

Episode Date: September 7, 2025

0:00 Intro 0:08 Older woman 7:41 Obsessed Learn more about your ad choices. Visit megaphone.fm/adchoices

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Are those from winners? Ooh, are those beautiful gold earrings? Did she pay full price? Or that leather tote? Or that cashmere sweater? Or those knee-high boots? That dress, that jacket, those shoes. Is anyone paying full price for anything?

Stop wondering. Start winning. Winners, find fabulous for less. Welcome to R-slash Best of Redditor updates, where OP gets a sugar mama. Our next Reddit post is from R-slash Relationships. I'm a 19-year-old guy, and I've been in a relationship with a much older woman, who's 39 for the last four months, and it's starting to feel really weird. I first met her when I took a part-time job at a local small business she owns,

which I no longer work at for unrelated reasons. She had been very openly hitting on me for several months before, but I didn't reciprocate, even though I did find her attractive, due to a combination of shyness and obliviousness. I'm not very good with women, and I'd never been in a relationship before. Eventually, she pretty much outright asked me if I wanted to stop by her place one night, and we wound up having intercourse for the first time. The relationship has been going on for a while since then, but there's a lot of things I'm finding that are really weird and off-putting, even aside from the age gap itself. First of all, she constantly wants to do sexual stuff with me at random times. For example,

back when I was still working for her, but after our relationship had started, she would constantly call me to her office just to ask me if I wanted to make out or invite me to feel her up. She also tried sexting with me regularly, even though I usually don't respond very well, since it's something I feel very awkward doing. She sometimes gets really upset when I'm not interested, too, which makes it even more awkward for me. Also, she's constantly getting me very expensive gifts, which I guess sounds nice in theory, but actually makes me feel really awkward, since I generally try very hard to be self-sufficient. For example, one time she bought me a fancy new laptop because she heard that I'd been using the same old one for several years, which put me in kind of a weird

position since I didn't want to get rid of my old laptop, but also didn't want to hurt her feelings. Finally, she's always texting me late at night, asking me to come over to her place and passionately hug her. And she sometimes gets really upset if I tell her I have other plans or I'm just tired. It's a 45-minute walk from my dorm to her place, so it's not just something that I can do casually. She's also constantly texting me drunk and rants about her ex-husband and how he stole the best years of her life, and about men in general and how they're stupid and shallow, and how she's glad that I'm smart enough not to waste time with trashy college sluts. Like I said before, I've never been in a relationship before, so I'm not really sure how much of the weird feeling

in my gut is caused by actual red flags, and how much is caused by the fact that I'm just not used to relationship stuff in general. Can anyone help me out here? Down in the comments, Down in the comments, someone says this, Sugar Mama isn't getting enough from her Sugar Baby. This isn't a normal, healthy relationship, if that's what you're wondering. When OP asks, what's unhealthy about it? Someone replies, She likes you because she can control you.

She buys you things so she can demand your time. You feel indebted to her because of the things she's given you. She tells you when you two are going to hook up. She tells you when you can touch her. I'd say she gets off knowing you're so inexperienced. and young. She likes having some younger guy at her beck and call. I would say that you're not in a relationship, at least not a boyfriend slash girlfriend or partner relationship. You've entered into a sugar mama slash sugar baby relationship. Yep, that's exactly what I was thinking. Then three days

later, OP posted an update. After having some time to collect my thoughts, I decided that the best decision would be to break things off since we obviously had different things we wanted in the relationship. I originally planned on doing this when I next saw her. That's not how things wound up playing out. Three nights ago after I made my first post, I got a very explicit text from her telling me she wanted to see me in half an hour and all the things she wanted me to do to her.

I politely told her I wasn't interested, and as usual, she started to get insistent and kind of upset. Since it seemed like the path of least resistance, I just told her then and there that, while I'd enjoyed our time together, I wanted something different in a relationship and wanted to break it off. She asked why, and I just told her that it wasn't working, and I don't want to get into a long conversation about it. For the next several hours, she kept sending me messages, asking me what was going on, why didn't I like her anymore, if there was anything she could do, etc. And I just kept telling her that I

enjoyed what we had, but I was just ready to move on. Eventually, the message just stopped, and I assumed that the whole thing was over. The next day, I awoke to find a ton of messages on my phone from her ranting about how she thought that I was different from other guys, but I'm just another stupid shallow butthole who chases after college horse, because I'm too emotionally stunted to handle a relationship with a real woman like her. A few hours later, to my shock and horror, she tried to ambush me when I was on the way to my dorm for lunch. She knows where I live, sadly. And she started laying into me about how I was a shallow, immature, ungrateful butthole, and she never wanted to see me again. Right, she stalks him and tracks him down

because she never wants to see him again, okay. A few hours later, she started sending me more nasty messages, so I decided to block her number. She later cornered me again when I was trying to get dinner and demanded to know why I hadn't responded to any of her messages. I told her that I'd blocked her number, and I didn't want to talk to her any further. And she went off on me again and said that I was an immature loser who would never find anyone else who's willing to touch my tiny dick again. This one really got to me, since I do have a lot of trouble with women. Yesterday, she ambushed me yet again when I was trying to get lunch and started laying into me about how I was too shallow, stupid, and ungrateful to appreciate a woman like her, how she hopes I die alone, and I'm

I just told her that I was going to contact the authorities and walked off. A few hours later, after informing campus security and the local police, I temporarily unblocked her number and sent her a message saying that I had contacted the authorities, and there was going to be trouble if she continued her behavior. She sent me a reply saying that I was being a cowardly piece of trash, and I blocked her again. She made no attempt to make further contact with me since then. Hopefully the situation has at least been resolved now, although part of me is still uneasy just because of how far she's escalated. I'm not going to lie, this has taken a fairly serious emotional toll on me.

One of the few women who's ever showed any interest in me, who I used to like and have some amount of respect for, suddenly turned into a complete psycho who hates my guts, and some of what she was saying did hit close to home at times. I don't doubt for a second that I made the right decision here. But part of me just wants to understand why she went so crazy so fast, so I don't wind up in this situation again. Sorry if that sounds melodramatic, but that's just where I'm at right now. Well, you know, I wouldn't say that she suddenly became crazy out of nowhere. I'd say that she was always kind of crazy.

She just went from being crazy and nice to crazy and mean. Our next Reddit post is from Throw Raw. My boyfriend and I have been dating for a little over three years now. He has one sister who's 25. This sister, I feel, is a little obsessed with my boyfriend, her brother. I was blinded by it at the start of our relationship, and just gradually over the last year, it's really been showing more and more. She'll do things such as call him over and over five to six times in a row, along with

like five to six texts if he doesn't answer his phone. We'll be doing things like hanging out with a friend or being on a date, and she'll just do this just to see what he's doing. Anytime we go somewhere, she has to know where he's going, what he's doing, who he'll be with, what time will be home, etc. A couple weeks ago, she came into his room while we were laying in bed watching a show and referred to him as, My love, but just to tell him his phone was going to die. My love, your phone is going to die. and then on another occasion she came into his room and like pet his chest his shirt was off as she was sitting down super unnecessary she had his location and she would watch it like a hawk 24-7 she would sometimes just show up to where we'd be without saying anything before coming i have a sister that we occasionally hang out with and while hanging out with her my boyfriend would get text from either his sister or her boyfriend saying thanks for cheating on us or thanks for the invite.

Just really immature stuff like that. Last Thursday, we were driving home from the store, and she and her boyfriend conveniently showed up on the same road at the same time. And when we ignored them driving next to us, it made her mad, so they sped past us and she flipped us off out the window. My boyfriend started a new job back in April, which made him extremely exhausted and tired, so he didn't really talk to her or anyone else,

which made her freak out thinking he was, so mad at her and went and complained to their mom about it, which then resulted in the mom asking me about it like I had something to do with it. I've expressed my concerns to my boyfriend, and he's seen the problem, but has a rough time saying anything to her, because then she'll get over-dramatic and again, freak out. He just recently stopped sharing his location with her, and she's pissed about it and keeps requesting his location. On the 4th of July, my boyfriend got really drunk, so I drove him home, and the second we walked into the house, she was quick to run out of the bathroom and take over taking care of him, even though I had it, and I'm

perfectly capable of taking care of him. I just feel like she's threatened and is low-key obsessed with her younger brother, and I don't know what to do. In the comments, O.P. Clarifies, they're 100% blood-related, the sister is a nurse, and she's been with her boyfriend for eight years and they're engaged. Then one year later, OP posted an update. Back in October, shortly after my original post, his sister finally moved out. That was amazing, and things calmed down for a while. Honestly, I've blocked out some of what happened, but there are a few major events that I remember clearly. At the beginning of this year, my fiancé and I were looking to buy a house about 35 minutes from our hometown. When we told his parents, his mom completely shut down and was obviously

upset. She tried to list every reason why we shouldn't do it, but I had answers for everything. Still, she acted like a child for days, barely talking, and when she did, it was to criticize the idea. In the end, we didn't buy the house, partly due to her lack of support and partly for work-related reasons. The final straw happened in April. Around 1 a.m. on a Friday night, I started getting multiple no-caller ID calls. I didn't answer at first, but then my fiancé started getting them too, so he picked up. On the line were a couple of girls claiming they had been with my fiance the night before and the week before sleeping with them. They were trying to convince me that he was cheating. I knew immediately that it was a lie. We recognized the voice. It was his sister and one of her

friends. They called like 15 times. They kept changing their story and they couldn't keep the detail straight. We finally confronted them by name and told them to stop. I was furious and got on the phone telling her, this is why we don't talk to you anymore. You need to grow up. You're almost 30. My fiancé told his parents about the prank calls, but they denied that she would ever do something like that. A few days later, his sister admitted it to him, she laughed it off and called it a joke. She didn't care and never apologized. That was the moment he completely cut her off. His mom didn't help matters. She ended up yelling at my fiance saying I was the new variable ruining the family. Then, at the end of April, it was his sister's birthday. We'd already decided

not to attend the family dinner because it was also my mom's birthday, and we were going to her celebration instead. During my mom's dinner, his mom sent him multiple texts saying that she was disappointed and that he broke her heart by not choosing her. When he didn't respond, his dad texted. When you come home, don't bring your woman with you. My fiancee went home to talk to them while I stayed at my parents' house. In the front yard, his dad lectured him about how blood is thicker than water, and no one should come before your blood family. My fiancé asked if his mom came first in his dad's life, and his dad said no, which honestly blew my mind. Fast forward to June, and his mom insisted we have a face-to-face family meeting. It was awful. I confronted his sister directly,

but she had nothing to say, so most of the conversation ended up being between me and her fiance. My fiancé did defend me, so I wasn't entirely on my own. Since then, there's been no further drama. His sister remains cut off from our lives. We're happy, we're planning to move out as soon as possible, and we're looking forward to our wedding. A lot of the comments are discussing the predictable question, which is, Does the sister have the hots for her brother? And, you know, I really don't know.

That could very possibly be one explanation, but I think it's probably more likely that the boyfriend's family is just super controlling by nature because the mom is obviously very controlling and manipulative. So it's possible the daughter picked up those habits again. Or, you know, could just be good old-fashioned incest. That was our slash best of redditor updates. And if you like this content, be sure to follow my podcast because I put out new Reddit podcast episodes every single day.