Anonymous Mailbag

It’s Tuesday, time for the anonymous mailbag.

As always you can send your email questions to me at

Okay, here we go:

“Let me start this by letting you know, I’m 24, and a virgin. I’ve made the decision to stay one until I’m married because I am a Christian, so yeah. I know, go ahead and make fun. 

Okay, now that you’re done with that, you should also know that I have had opportunities to lose my virginity before, and have chosen not to. 

The latest chance to lose my v-card came in what I think to be, the weirdest way yet. One of my best friends has been dating this girl for quite a while, and they are extremely sexually active. That’s fine, I don’t have any problem with that.

Here’s the thing: I always kind of thought that his girlfriend was kind of attracted to me in a weird way, but I never put too much stock into it because they are dating. 

Well, my buddy, knowing that I am a virgin and am currently single, drunkenly sent me a nude picture of his (admittedly super hot) girlfriend. I was pretty surprised. He said “I know you’re single, let me help you out.”

I definitely thought it was weird, like he assumed I couldn’t find nudes on the internet or something? Well the next day, I told one of our other friends about this and told him that I always thought this guy’s girlfriend had a thing for me and that they were trying to “warm me up” to some weird sexual thing. He said not to think too much about it, the other guy was drunk and no one meant anything by it. So I took the advice and I didn’t think much of it and kind of moved on. A couple of weeks later though, he tells me that his girlfriend knows I have the nudes of her, and thinks is extremely hot, so she took more nude pictures for him to send to me directly. BOOM. Everything confirmed.

Then comes the big ask: apparently she has a thing where she wants to take a dudes virginity, and has decided that she wants to take mine. They had it all planned out, next time I’m in town we would do it. 

So my friend asked me to sleep with his girlfriend, and was bragging about how I wouldn’t last, and how it’d be great. This is freaking weird, right? I’m not talking about morality, I mean just in general, this is a weird thing. Who in the real world does this? I mean, I get a girl wanting to take a dudes virginity, I get a friend trying to help a friend out to get with a girl, but I do not understand how you can willingly let your girlfriend sleep with one of your best friends. And not only let it happen, BUT ACTUALLY SET IT UP FOR THEM. 

I’m not going to do it, because it’s not a good idea for obvious reasons. First, I’m saving myself, and second, he’s my friend and this would definitely be the end of the friendship. I just need to get someone to acknowledge that this is very strange, and not normal, right? I’ve never heard of this happening in real life. Seems like the beginning to a porno.” 

This is definitely uncommon, but does it rise to the level of weird? I don’t necessarily think so.

Let’s break this down.

First, the idea of a woman (or man) wanting to take someone’s virginity isn’t that uncommon. That is, I can certainly see how that could be a turn on to someone and there’s certainly a substantial group of people that find this idea attractive. Personally, I think the fact that you’re a virgin is just the excuse she’s using for wanting to sleep with you.

Now the next step, how common is it for a partner to help acquire a partner for the other person to engage in sex?Well, this wouldn’t be uncommon at all if, for instance, there was an interest in a threesome, right? What’s uncommon here is that a boyfriend is finding his girlfriend another guy to sleep with, but I think that uncommonness is canceled out by the fact that she’s hot and he’ll likely do anything to keep her happy.

It’s long been my belief that if a hot girlfriend wants to do something sexually her boyfriend will probably relent eventually. In other words, women, by and large, act as the restraint on male sexual desires more often than not. Think about it this way, gay men report an average of 50 sex partners in their lifetimes compared to an average of five sex partners in the average heterosexual man’s life. (This was data from like twenty years ago so the heterosexual and gay sex numbers may be higher now.)

Regardless, the key point here is that gay men have ten times as many partners as straight men.


Because gay men have two male sex drives and men will enter into all sorts of risky sexual behaviors. What usually limits that risky sexual behavior? Women.

There are relatively few times when a woman suggests a risky sex move and a man rejects it.

In fact, women with risky sex drives are much sought after because men consider their behavior to be super hot.

Think about it this way, if a hot woman gestures to you in the Wal Mart parking lot and when you get close to her she’s naked and masturbating, most men would consider it the most awesome part of their day. If a man does this to a woman, he goes to jail.

So your friend has one of these women and she’s made a request he’s not threatened by — she wants to have sex with you. Maybe it’s because he’s banging someone else on the side, maybe it’s because he knows he’s not going to end up married with this girl, maybe it’s because he finds the idea of her banging other men to be hot, maybe it’s just because she’s hot and he’s willing to do anything to keep her.

Who really knows?

So I think the behavior is uncommon, but I’m not sure I’d say it’s weird.

I think as sex becomes way more commonplace then who people have sex with becomes less of an issue. That’s even more so when, in theory at least, you can avoid getting pregnant through sex.

Think about it, for most of human history if your significant other slept with someone else then she might get pregnant and you’d end up raising someone else’s child as your own. I mean, the risks of sex outside of a relationship were massive. Think about it, barring a prolonged separation between a husband and wife it was virtually impossible to know your wife had cheated on you.

So there was a huge premium on fidelity from men.

Women, on the other hand, always know that a child is theirs and don’t bear this risk.

Well, with sex becoming more commonplace and birth control becoming more common as well, monogamy is less of a societal necessity and the risks associated with having many sexual partners have become substantially diminished.

I mean, don’t get me wrong, risks still exist — witness the rise of STDs with the prevalence of dating app proliferation — but the truly massive risks — you die from having sex or get pregnant and your life changes forever — are pretty much nonexistent if you’re reasonably safe.

I understand that you want to stay a virgin for religious reasons, but I think once you start having sex you’ll realize it’s not as big of a deal as you’ve made it out to be by waiting for marriage to start.

In the meantime, do blow jobs count?

If not, I’d agree to have sex with the girlfriend and then tell her you’re only willing to let her give you a naked blow job.

Or you can have anal sex with her — come on, this chick is definitely in to that too — and claim you’re still a virgin after that too.

Seems like a huge win for you here, honestly.

Good luck.

“Much like you, I’ve got man boobs. It’s cool. I’m pretty skinny and I’ve had them for 20+ years, so it’s not due to my weight and it doesn’t fluctuate with how much I work out. They’re just……….there.

I think it’s just a weird anomaly that I happened to inherit. Due to how well things have gone financially and personally in my life, in all honesty, I haven’t focused much on them. My wife who is so unbelievably attractive…and has huge TRACTS OF LAND…says she doesn’t care (we’ve been married over a decade) and also says she “never noticed them.”

When I look in the mirror, though, I’m pretty sure my man boobs are bigger than they should be. I’m just really not a big fan of being shirtless in public. Part of me wants to have surgery to take care of it, but part of me doesn’t give a damn because of how awesome my life is. I just don’t want to eventually make my kids uncomfortable.

Talk to me, bro. What would you do?”

You know you’ve made it in life when you get an unsolicited email from a cosmetic surgeon who has seen a photo of you topless and is willing to give you free man boob surgery. (This actually happened to me).

Here’s my general thoughts on the pool in general — most people are way more concerned with what they look like in a swimsuit to worry about what you look like. Plus, you aren’t fooling anyone by wearing a shirt. I think guy in shirt in the water at the pool looks way more ridiculous than fat guy does.

Having said that, I may have man boob surgery one day because the entire concept of writing about man boob surgery is so insanely funny to me that I think I could probably get my next book deal sold just from writing 10k words about my man boob surgery.

Come on, is there a single person out there who isn’t reading every word about my man boob surgery? If I paired it with my story about losing $50k on pants, I’d have a bidding war in publishing houses.

My biggest concern, honestly, would be I don’t want to pull a Joan Rivers and die on the operating table during man boob surgery.

What a way to go.

I also wonder if it’s actually successful. Because the only thing worse than having man boobs would be having man boob surgery that doesn’t work and makes things worse.

Anyway, you know how people get long hair cut off and donate it to cancer patients? Could I donate my excess boob fat to women with small boobs? Could I pick a donor? Y’all know I hate to draw attention to myself, but this seems like a heroic thing for me to do.

“I went to my neighbor’s for a party recently and I met this girl and we instantly connected. So much so, we were making out within 5 minutes and were having sex within an hour. I definitely wouldn’t consider her hot but she was cute enough, cool, smart, and we had great sexual chemistry.

Fast forward to the morning – an off-handed comment lead us into political discussion. I am Trump supporting Republican living in Chicago, and she, like the vast majority of girls here, is a Trump hating liberal. Needless to say, things quickly soured. While we were cordial after a little heated discussion, I drove her home, gave her a kiss, and said goodbye.

My question to you is – what is the proper approach here? I have her number and we even texted a little on Sunday.

I’d like to hang out with her again (more like to have sex with her again) but am a little apprehensive considering that this will never materialize into a potential long term relationship. I almost feel bad about just “using” her for sex, but I really enjoyed our night minus the politics.

Your thoughts?”

As long as you’re up front about the relationship’s seriousness, why not keep having sex? (By being up front, I mean not leading her on and claiming you see yourself marrying her in order to keep having sex.)

Plus, not to scare you, but if every guy and girl who thought, “This isn’t going anywhere, we’re just having sex,” was actually correct there would probably be three billion less people on the planet.

So what if you two disagree about politics?

A huge percentage of married couples cancel each other’s votes out every time they enter the voting booth. We need more people interacting with different opinions in this country instead of less. I think that’s true in relationships, friendships, everywhere in modern American life.

I’d keep hanging out with this girl if I were you.

“I have a real first world problem.  The country club I belong to is going through a renovation project, so we are playing a different course while ours is closed.

I have a Saturday morning group that has played together for several years.  Three of us are right around 40 and our other guy is in his upper 50’s.  We are all low handicap’s and have a lot of fun together (basically it’s all of our competitive outlets).  

So the older guy works with one of the other guys in the group and is top level management in their company.  He is a great guy and we have a lot of fun with him.  Very good player as well, hardly ever misses a fairway and has a stupid good short game…makes you sick!

The issue is we play the back tees and this new course we are playing is a lot longer and more difficult than our home course.  He just can’t hit the ball long enough to be competitive out there, and he seems pretty miserable about it.  The answer is obvious to me.  Move up to the regular men’s tees…right???  The guy that works for him doesn’t want anyone to say anything.  

To me that’s the fair thing to do and everyone is happy and we are back to normal until our club opens back up.  What’s the play here?”

The guy who drives the ball the farthest should announce before you tee off this weekend, “This course is too damn long and I think it’s going to screw up my game when we get back to our normal course. Why don’t we play the next tees up?”

Then one of you should immediately respond, “I’m glad you said that, I’ve been thinking the same thing.”

The second person should turn to the remaining two guys, including the guy who isn’t long enough off the tees, and say, “That okay with you guys?”

Boom, problem solved.

The other suggestion would be letting him hit from the closer tees while you guys all play from the back tees, but that’s a non-starter I think.

Of course, you could just let the old guy suffer from the long tees, but it sounds like the overall competition is being lessened based on his struggles on the new course. He’s twenty years older than you guys, nearly, so equalizing the game makes sense to me, especially since this new course is temporary and you’ll eventually be back on your regular course.

Of course, if they adjust the tee boxes in a big way on the old course and he’s not able to play from the same tee boxes as you guys going forward then you’ll have a new dilemma to solve.

But in the meantime, I’d all move up and play the closer tee box.

“I was talking to a bartender a couple weeks ago and she seemed interested in me. Same age (27), thought I was funny, gave me a free gift certificate, and even gave me two free shots.

I left my card with my cell phone number and said here’s my number if you want to go out sometime. She texted me and she told me when she was available and I said that works for me just let me know what time.

However, she never texted back to confirm the date for 4 days. I figured she was not interested so I moved on and went out with another woman (who is a little hotter, but not by much). The night I went out with the other woman the bartender texts me (4 days later) and said she’s sorry she didn’t get back to me but her friend had a miscarriage and it’s been hard on her. 

Is this a real or fake excuse? I’m not even sure the story is true, but even if it is true she can’t send a text at the hospital? Should I give her another shot? She’s hot enough that I’m considering it.”

I think it’s probably a real excuse — there are many more legitimate excuses she could make — but the bigger issue here is, why do you care?

A hot woman wants to go out on a date with you and you’ve already asked her out so we know you want to go out with her too.

Who are you, the president? Does a four day alteration in when you go out really change that much in your life?

Have fun.

Send your mailbag questions, anonymous or otherwise, 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.