Mailbag: Your Significant Other Having Herpes, Joint Bachelor/Bachelorette Parties, And Trouble With Prophylactics


Welcome to the PGP Mailbag, wherein I will answer questions from you, our readers. Send your questions to All topics welcome.

Hey Dillon,

Love your advice in these heated topics so far.

So been dating a guy for a couple weeks now and we have been having some of the best sex/dates during that time. Recently he just dropped the bomb on me that he is not clean and has herpes, but it is not an issue since he has not had a breakout and is on antibiotics. Real forgetting sarah marshal situation. Like this guy a lot, but obvious red flag that he did not say this before we had sex even though he claimed he said it the first night we had sex, but we were drunk so I don’t recall that and feel like I would.

Everything I’ve read says that it is perfectly okay to have sex in between breakouts, but to obviously wear a condom and closely monitor if you feel you are going to have a breakout. I got tested and it was negative. We like each other enough that I have a couple vacations planned with him coming up. What are your thoughts on continuing to date this guy? Worth the risk? I feel shitty having to end a good thing based on someone’s shitty circumstances.

The first thing I’ll say is that the herpes conversation needs to occur early on, and while both of you are sober. Upfront honesty and clarity. That’s a serious discussion with potentially lifelong ramifications.

I’ve been staring at this question for a good ten minutes trying to come up with an answer for you. It’s a tough one. If I met the woman of my dreams and she happened to have herpes, would I stay with her? I think I would find a way to talk myself into it, yeah. The disease is manageable from what I understand. I think my fear would obviously be contracting it and the relationship not working out.

I think you have to ask yourself if this person potentially means enough to you to live with the perpetual risk of getting herpes. Not recalling him informing you about the herpes, though, that’s the red flag. You should get to the bottom of that somehow. If he didn’t tell you until after you slept with him, that is very fucked up. VERY fucked up.

“I feel shitty having to end a good thing based on someone’s shitty circumstances.”

You really shouldn’t, because it’s about your health. You are always your own priority, especially when it comes to your well-being.

Hi Dillon,

I’m in a few weddings next year and bachelorette party talks have begun. My friends are all about going big on our bach parties, we normally fly some where and it runs to be at least a $1,000 weekend. And I’m not complaining about that, we always have an amazing time are happy to do this for our friends.

Sounds perfect, right? Wrong.

I recently found out that the bride and groom are doing a jack and jill bachelor party. If you’re unfamiliar, its when the bachelor/ bachelor party is combined. I do not want any part in this nonsense. I’m not looking to throw down this type of cash to hang out with a bunch of dudes I don’t know. I talked to some of my friends and none of us are happy that this is the plan.

We’re convinced that the groom-to-be is behind this shit but have no idea how to get this changed without upsetting the bride. Her reasoning for wanting to do this combo party doesn’t make any sense.

My question is, even though I’m in the wedding and this girl is one of my best friends, do I HAVE to go? I feel as if I’m upfront with the bride she will be super upset and things between us will get awkward.

Jack and Jill bachelor/bachelorette parties are traaaaaaash, and so are brides and grooms-to-be who choose them.

The literal point of bachelor/bachelorette parties is to celebrate one last hurrah as a “single” person before getting locked down for the rest of their lives. That’s why it’s called a bachelorette party. This defeats the purpose. This couple sucks and I hate them and I wish them a very mediocre marriage.

Look, it’s your money, your time, and your upset friend to deal with. So, you don’t have to go, but also yeah you pretty much have to go. Although this couple is totally blowing it, the wedding, and all related activities, is their chance to be as selfish as they want to be. You should go. You might be surprised and have a great time.


Love reading mailbag submissions, hilarious stuff.

So essentially I’ve been upping my game in the sack these past two years and for some reason most of the girls I’ve slept with we use a condom and in the drunkin slurr of the night it always comes off for a good 10-25 seconds and we keep going then proceed to put on a new one.

This keeps happening and I keep getting tested to make sure I’m clean, but eventually this shits gonna catch up with me. The girls always seem to be fine with it too but each morning I’m like damn that happened again? Any thoughts on how to prevent this from happening even when we plan on using protection?

Much love

Wise guys in the comments are going to say it’s because your thing is too small but honestly I have no idea why this is happening. Maybe get a rubber band, do the thing where you twist it and double it up a few times to make the circle smaller, then put it at the base of the condom once it’s on your piece. Note: I’m kidding. Please don’t do this.

Can anyone explain what’s happening here or have advice for him? Does our man have a skinny hangdown or what?

Hey Dillon,

So, I’ve been talking to a new guy for a couple months now. He’s a little older, 33 and I’m 26, which is totally fine, I actually prefer older to be honest. But he’s going through a divorce and has two kids (the divorce isn’t yet final, but the papers have been filed). Communication is awesome and he tells me if there is something bothering him and we’ll talk about it if he wants to. Problem is that the divorce is getting messy. The ex appears to be crazy (as most people assume), but she’s making it difficult for him to see his kids, two boys, and I can tell immediately when talking to him if something is up because he gets so down.

We’ve talked about taking it slow, which is fine with me. To make it a little more complicated we live about an hour away from each other and his weekends are when he has the boys (whom I haven’t met yet, which is fine, no need to rush that). We try to make time to see each other and do so about once a week, but we text throughout the day. I guess I’m looking for any advice you have on how to handle the situation. I know you’re recently or semi-recently divorced, but have a much better relationship with your ex. Any advice would be appreciated. I definitely care for the guy or I think I would have just ended this sooner. Just hoping to get through this part so that we could see where this goes, if anywhere. Thanks!

Advice Seeker

If his process is anything like mine was, he’s on the tail end of what’s probably one of the worst periods of his life. I went through some pretty dark shit when I realized what my journey onward would look like, and like you said, I get along amazingly with my ex. So, his experiences could be even worse than mine were. Depression during times like that can creep in on even the most emotionally stable people. It truly just fucking sucks.

Kids are involved, too. That takes this to another level. From living the family life, being constantly surrounded by your wife and kids and in your home, to being alone and in a new place and dealing with the reality that you have to hit the reset button on a lot of aspects of your life. It’s just a lot to handle and process.

The good news is he’ll likely come out on the other side with a new lease on life. It took me many months, but I’m currently as happy and stress free as I’ve probably ever been. If you care about him, and it seems like you really do, be there for support while he deals with everything he has going on, which is a lot, and most of it is very unpleasant. Be patient. Better times are ahead.

Hey Dilly-

I’ll be brief. How much do you tip your barber around the Holidays? I usually give him 25% during the year, but I’ve heard a few different opinions on cuts during the Christmas season. 50%? 100%? What’s proper etiquette for this?

I don’t know what this says about me but I didn’t know that heavy holiday tipping was a thing? Is this true? I’m a %25 tipper, too. That extra 5% is because I go to the same person every time, so we know each other.


The more questions I receive, the better this series is going to be, so send me your Mailbag questions to and please put “Mailbag” in the subject line.

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Dillon Cheverere

Dillon Cheverere is the Vice President of Media for Grandex, Inc. Email:

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