Anonymous Mailbag

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It’s Tuesday and the anonymous mailbag is here to solve all your life’s problems.

I’m down in Palm Beach this morning, getting ready to head over to Mar-a-Lago for the Clay and Buck Show. We will be live off the top of the show with President Trump at 12 eastern, 9 am pacific. I encourage you guys to listen along live or download the podcast later.

In the meantime, as always, I’m here to solve all the problems in your lives.

You can send your anonymous mailbag questions to, anonymity guaranteed.

Okay, here we go:

“My girlfriend often has dreams about me having sex with other women. All apparently involve people that she knows, but some of whom are women that I’ve never met. She is evasive when I ask her for details about these dreams. I’ve never slept around on her when we have been together. I figure that it has to be one of two things: 1.) She has an insecurity about this for whatever reason, and/or 2.) She has a secret fetish about envisioning me having sex with other women. What do you think it might be?”

My best guess is that she’s wildly insecure about your relationship and she’s using these dreams to see whether or not you are more interested in her friends than you are in her. The moment you express any interest at all in sleeping with her friends, boom, she’s trapped you into confirming her fears. (Side note: there are very few men who have ever lived who are not going to be interested in hooking up with her hot friends. I’m not judging you in any way for this, just pointing out that if you mention this to your boyfriend and he says he’s not interested it’s probably because he’s fearful that you’re setting a trap for him.)

But that’s my best guess, you know her better than I do.

Maybe she’s truly trying to see whether you’d be willing to have sex with her friends. Of course, there’s still a big deal here, the friends would have to be interested in sleeping with you too.

The next time she brings up one of these dreams with you, simply ask, “Why do you think you’re having these dreams?” You say she’s evasive about details so begin not by quizzing her about the dreams themselves, but why she thinks she’s having them. Allow that to lead into the biggest question here, which is this: does she enjoy these dreams, that is, are they fantasies or are they nightmares? Everyone knows the difference between these two types of dreams, again, I wouldn’t focus on the specifics of the dreams, I’d focus on the emotions they elicit from her.

As part of this conversation, you need to be non-judgmental. It’s even possible that she’s attracted to these women herself and she feels more comfortable seeing you with them than she does thinking about herself with them. This is all part of a larger conversation you can have, but if you can get her to answer these questions, you’ll be more likely to get the answers you’re seeking.

It’s also worth noting that there’s a difference between something that’s a fantasy and something that’s a reality. The fantasy might be sexy to her, the reality likely isn’t anywhere near as hot and is way messier.

But, again, if I had to bet here, I’d say the chances that you have a girlfriend who wants you to hook up with other girls she knows is really small. I tend to think this is rooted in her own insecurities over your relationship with her and she feels you’re more interested in them, and other girls too, than you are in her.

It’s even possible she’s entirely making up these dreams just to gauge your reaction.

Good luck with the conversation, but be careful in how you approach it. This is a bit of a landmine.

“So I just started dating a girl a couple weeks ago. She’s awesome, beautiful, sane, the whole package.

Well, it turns out the bat shit element is her ex boyfriend who as I just learned owns her house and doesn’t seem to get they are broken up.

This dude shows up last week out of the blue when she wasn’t there, let’s himself in, buys a bunch of groceries before a big snowstorm, and blows up her phone wondering where she is. (She’s w me in my gated community, never been happier to be bougie) she is panicking and tells me the situation.

He sees some of my clothes there and freaks the hell out also, takes pics of them and sends them to her, creepy prick. She tells him to get lost, he does, and then last night shows up at 4 AM inside the house, scares the shit out of her and her dogs, I think with the intent of catching me there with her and starts asking a bunch of questions about me.

It’s his house, he doesn’t want to give her a lease, but wants her to live there and promises to leave her alone. My suggestion to her is to get cameras/a lease or a restraining order. Because this guy isn’t going to leave her alone otherwise and I really don’t want her harmed by this crazy bastard or have my pecker shot off if I’m there.

What are your thoughts/ ideas on any recourse she has?”

My first thought here is your new girlfriend is a side chick, a gold digger or has been using this guy as a sugar daddy. Granted all of these relationships have subtle variations, but they all essentially boil down to an attractive woman selling her sex to a wealthy man in exchange for his financial support.

It’s his house and he’s allowing her to stay there for free. How many women do you know who are completely normal who live in a house for free that their ex-boyfriend provides them? If this girl really wanted to cut ties with this guys completely, she’d move out of the house.

But she’s not doing that.

Why not?

Because my bet is she wants to keep living in the house. If that entails maintaining a relationship of some sort with this guy, so be it. Because the easiest solution, by far, to this issue is she needs to move out of his house and not live there any longer.

It seems quite clear based on the details you’re conveying that this guy is controlling and feels that as long as she is living in his house, he believes he has the right to enter and exit his home. This gets messy because he doesn’t have the right to threaten her inside the home, but he does have some legal rights to the premises given that he owns it and she isn’t an official tenant. If he wanted to, he could definitely evict her from the home.

There are other details that could matter here in terms of when he can enter the home — is he also living in the home, for instance, or does he have his primary residence elsewhere in the city? — but rather than examine all of these legal complexities, this isn’t a particularly challenging solution — move.

Sure, she could ask for a lease, which would provide her some measure of privacy and legal security inside the house, maybe, but based on the details you’re sharing there’s no way to justify choosing to stay living in his place. He’s stalking her, at least on some level, and appears to believe this relationship is still ongoing.

This is why you want to have a serious talk with your girlfriend. I feel like you’re willfully blind here and ignoring some of the red flags this girl is putting out, maybe because you’re enamored by her hotness. Right now you’re only hearing her side of the story. What is she telling him? And is she leading him on so she can continue to live rent-free in his home? Remember that you’re only getting the details that are beneficial to her. This guy may really believe he’s still in a relationship with her. Certainly bringing groceries to the house would be illustrative of that. In essence, what would this guy say if you talked to him about the relationship?

The integral question you have to answer here is this, why do you want to be in the middle of this relationship at all? Do you want some strange guy potentially barging in when you’re with her? Do you want to face physical danger as a result of her life choices? That seems like a really bad choice by you.

I’d be pretty clear with this girl and say this, “If we’re going to date, you have to find your own place to live outside of this guy’s house.”

If she’s not willing to do that, I’d cut off the relationship. There are plenty of other girls out there and if she’s insisting on staying in his house, it feels like to me she’s using him as a sugar daddy. There’s nothing illegal about that choice by her, but it’s not something I’d want to find myself in the middle of if I were you. You say she’s awesome, beautiful and sane. In that, she’s not alone.

She moves to a new place or you find someone new.

Put simply, I’m not sold this girl is that great of a catch.

“Hi Clay, I currently live with three other roommates. We each have our own bedroom but share a bathroom area. One of my roommates has a long-distance girlfriend that came into town for Valentine’s weekend. Normally they just stayed in their room, but I came home one afternoon and they were loudly fucking in our shower. I understand that they haven’t seen each other in a while but they have a room to do it in. One of my other roommates constantly brings girls home and he bangs them in his room and keeps it private, so why shouldn’t they? In your opinion, what should be the policy with roommates in terms of having females over and where to have sex?”

The primary place to have sex should, of course, be your bedroom, but I feel like you’re being kind of a pussy here.

Let’s start here: how many bathrooms are there in the house? Surely that’s not the only one in a three bedroom apartment or house, right?

Presuming you don’t have to poop yourself if you come home and find your roommate and his girlfriend in the bathroom going at it, you should get over this. He has a long-distance girlfriend. It appears in this situation they may have started hooking up in the afternoon without you there and then you came home and found them in the act in the bathroom.

If you hadn’t come home in the middle of the afternoon, you would have never known about this.

Let’s take it outside of your roommate situation and put a hypothetical in your direction: if at some point you have a hot girlfriend who wants to have sex with you in the shower, are you going to say no to her and insist you stay in the bedroom because you’re worried about upsetting your roommates and using the bathroom for sex? Or are you going to Lewis and Clark yourself into the bathroom and explore the fertile terrain?

I think you’ll go full Lewis and Clark.

(Side note, am I the only person who still marvels at the idea that warm water to take a shower with every day costs virtually nothing and is everywhere in the country? I spend an inordinate amount of time thinking about how amazing it is that we have, essentially, unlimited safe water, both hot and cold, to use as we see fit with no issues. Do you know how amazing almost every human who has ever lived would find this? It’s truly remarkable. Also, am I the only person who thinks about things like these on a daily basis?)

Anyway, my point is, as I stated above, I think you’re being a pussy here.

If I were you, I’d be asking this girl to bring a girlfriend with her the next time she comes to town for a visit. If she’s fine having loud sex in the bathroom shower and doesn’t care who hears her, she’s probably got some fun friends too.

Focus on that.

The only way I can see this being an issue would be if your buddy’s girlfriend essentially moved in with him and you couldn’t use the bathroom, for instance, to get ready for work in the morning because she was monopolizing it. But that’s not the case here at all. This was a one-time event on a short visit.

Instead of complaining about the loud sex, you should be asking her if she has any friends.

Good luck with that.

“I’m a 39 old single mom of two kids and my boyfriend is 26 years old. We have been together for 3 years now and he moved into my house with me and the kids 6 months ago. He has been such a great mate, lover (we’re great in bed together), and father figure to my kids that I could ever ask for. We’ve talked about marriage but I’m a little uncomfortable with our age gap even though I love him with all my heart. With that said though I think would I really want a guy my age when I get to make love with a cute young guy? Do I need to just get over my insecurities and marry him? Is there something to look out for here?”

Your email talks a large amount about what you want, but I think a huge part of this equation is what does your boyfriend want? You say he’s great with your kids. Well, does he want kids of his own? Do you want more kids? This seems like the most important conversation you guys should have before you decide about your future.

It has been my experience that most guys in their twenties haven’t thought that much about kids. That’s because, in general, guys don’t have to think about the age they want to have kids, we have a huge age range to make that choice. Your boyfriend has stepped into a very adult relationship, he’s helping to raise kids, living in a home with a grown woman, all of these things suggest he’s more mature than your average guy. So has he decided whether he wants kids of his own, potentially with you? If so, are you willing to have another kid as you approach forty years old?

You talk a great deal about what you want in your life, but you didn’t tell us at all what he wants. Have you asked him? In order for any relationship to work, the couple has to communicate well. That’s even more the case when, let’s be honest, the gap between what a 39 year old woman wants and what a 26 year old man wants can be quite different. And what if his life ideals change? In five years he’ll still only be 31, that’s not very old for a dad at all. But you’ll be 44. That’s getting very old for a mom. This isn’t just a relationship question, it’s simple biology.

Finally, you’ve already integrated this man into your life with your kids. What do your kids think of him? Have you contemplated how difficult it might be for these kids, who already don’t have a dad, to invest a great deal of love in the new man in their household and then have him leave too?

Ultimately you’ve written a question about your future with this man, but you haven’t really talked about what he wants or how your future impacts what your girls want either. In fact, you didn’t even tell us how old your girls are. What you want matters, but it has to make sense in the context of your family too. And what you want has to square with what this guy wants.

Only you can vouch for his maturity, but many people’s life goals change quite a bit between 26 and 40. Will the same be true for him? Who knows? But at a minimum, you need to have a more in-depth conversation about the future than you’ve had so far.

Only then can you answer the question of whether the two of you should get married.

Okay, I’m off to Mar-a-Lago.

We’ll be ready to roll with the show at noon eastern with President Trump.

In the meantime, keep the questions coming to, anonymity guaranteed.

Written by Clay Travis

OutKick founder, host and author. He's presently banned from appearing on both CNN and ESPN because he’s too honest for both.


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  1. Awesome/Beautiful/Sane:

    Dude.. your no. 1 suggestion here is for your new girlfriend to get a lease at her ex-boyfriend’s house? Even if you don’t want a serious relationship and just want to smash this is an awful idea, downright retarded. Don’t be a chump ass Cap’t Save-a-Ho. If she isn’t totally worthless she’d be able to move and get her own place.

    • Yep, absolutely. And she’s living in a house that her ex is paying for the ex is 100% still tapping her. There’s no two ways about that.

      As for question 2. There’s only one solution, move out and get a place to yourself. If you’re living with 3 roommates you’re just going to have to expect to see some bumping going on from time to time.

      • Heard that. If dude is just trying to have one on the roster then nbd, but it sounds like he’s emotionally invested. He’d be dumb not to assume she’s not still bangin the “ex”.

        And question 2: Yup. He should be happy for his friend and keep it pushin.

    • Zero chance that is her “ex” boyfriend. She sounds like the kind of girl who will go back and forth to whoever is giving her more of what she wants. For instance, this guy has a house in a gated community, which would impart that he does pretty well for himself. Only a matter of time before #3 boyfriend comes along or she “officially” gets back with her ex, that she never really left

      • Might be her ex but all her shit is still at HIS house so you have a point, not officially over. It would be one thing if they shared a lease but ole girl is staying there for free w/ no contract and is still complaining about it. There’s a reason she hasn’t left.

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