Dear John (Vol. 3) - Pitting Women Against Each Other

Welcome back to another edition of Dear John, the blog where I field questions from strangers on the internet who want advice from a 32-year old man with a handful of addictions who wears sweatpants to work every day at a failing office. I did however get a haircut for the first time in 6 months yesterday, which means I'm more cleaned up and presentable than every before. So if there were ever time to heed my advice, now is that time. 

Dear John,

I recently moved to a new city across the country from where I grew up on an absolute whim. Going into it I didn't know a soul, but after my first few weeks here one of my sisters’ friends who I knew merely as an acquaintance of my sister and had only ever been associated in that manner, moved in somewhat close by. Since we both knew nobody here, we began hanging out, going on hikes and going out to the bars/breweries together. In my head that’s all it was, a person to do things with in a new city where I had essentially no friend base. At least I thought it was until I was sneak attack kissed (followed by a corny movie-esque “was that stupid”), after the bars one night. I didn’t necessarily like it, but my personal desire for the admiration of others (not a narcissist just self-conscious), combined with my avoidance of awkward situations prompted me to say, “I don’t think it was stupid at all”. I brushed it off as a drunk act and just went on about my life for the next week. The next weekend came around and we went out to drink again as if nothing happened. I may have touched lips with her roommate, this time on my own accord. I know hind sight is 20/20 and it may have been a stupid decision but in the moment I was seeing 40/40, one in each hand. So now awkwardness is at an all-time high, I don’t even know if I should be around them anymore and in the meantime what the hell do I tell my sister. Or don’t I? Do I have a kissing addiction?

I can't help but notice you forgot to describe either woman's face and breasts in great detail. It's going to be difficult for me to provide you with sound advice unless I have all the necessary information at my disposal.  Either way, you've got yourself in a love triangle of kissing. The easy/cool guy answer for me to give you would be to use your incredible charm to seduce them both at the same time and have a marathon 6-hour threesome. I'm not telling you not to do that. If you have that in your bag then by all means. But if that's not a realistic option, I recommend you find a way to pit them against each other. Perhaps send a bouquet of flowers to their home. Don't address them to either girl. Make them wonder who the flowers are for. One of them will probably just claim the flowers. They may not even talk amongst themselves about them. But it will become an elephant in the room, and will create an air of competition in the home which will naturally lead them into an arms race for your cock. Take this as far as you can until it blows up in your face. You've already kissed them both. You're in too deep now. Might as well do something self-destructive with the situation. 

Also, don't tell your sister. Not yet at least. She's either not going to approve or she'll try and help. If she gives you an assist, the thing you know, as you're sharing one of your famous drunken forty-in-each-hand kisses, your sister's face is gonna pop into your brain. Then you're basically doing incest. That's how that works. 

Dear John,

I’m 42 finally back into dating scene. A friend’s gf hooked me up with her 23 yr old sister. Very nice body decent face. Convo is me explaining mma/boxing fights, fb/bball game, science and history. Now she is trying to get involved by bringing up articles she reads about random stuff. Should I feel good she’s trying? Should I ignore the overall ignorance young people show? Or should I just get out cause I’m an old ass? I can’t see it going long but yes bad boyfriends and daddy issues are probably involved. I just don’t ask personal stuff. (8months going) 

Thank you for specifying "nice body decent face." Now I know exactly what we're dealing with here. Honestly, it's kind of sweet that she's trying. Even if a couple days ago she turned to you and said, "Did you hear Nick Saban, Alabama's Head coach retired after the season?" or "I just read about this Hitler fellow, sounds like he was a real rascal." You gotta give her credit for trying. 

It all just depends on how much you're mentally able to put up with. If she asks a couple of dumb questions a day that briefly make you cringe, but you're able to get past it a few minutes later, then you might as well ride it out a little longer. But if you've reached the point where she's grinding your gears hard enough that you're fantasizing about tossing her a toaster while she's in the shower, or cutting the brakes on her car before she leaves for work… that's when you gotta get out of there. Whatever you do, you can't murder her. That's of the utmost importance.

Dear John, 

I am 65 years old. I was in good shape until recently when I developed a heart condition. While the doctors are figuring out how to fix my heart, it's been 4 months, I have been banned from working out and having sex. I think dying during sex would be an awesome way to go out. But my wife refuses. I told her if it was good enough for Rockefeller, it should be good enough for me. ( ask Large for reference ) how can I convince her to resume having sex? 

Idk, hold a gun to your own head and threaten to blow your brains out unless she fucks you immediately. 

Actually, no that's a little bit extreme. But what you can do is engage in other destructive behavior's in place of having sex. Take up drinking a fifth of vodka a day. "Well if I can't have sex then I have to spend my time doing something". She can physically stop you from fucking her. She can't physically stop you from drinking yourself into a coma every day. Or you could buy a motorcycle and spend your extra time driving 100 mph down the freeway without a helmet. Or do a combination of both. Make having sex the lesser of two evils.

Dear John, 

When my girlfriend and I first started dating, she asked how many girls I had slept with. I wouldn’t answer. Finally I was sick of her asking and I told her, 12. However, the amount was more around 55-60 (humble king). Now we have been dating for over 4 years and I’m always worried someone from college or before we were dating will talk about nights I was single or just say something regarding the number. We men are stupid people. If this happens, does she have the right to be mad? How do I weasel out of it if she was to find out? Thanks for your help ahead of time. 

Just ride out the lie. How likely is it really that your girlfriend is going to run into an old friend from college who walks up to her and says, "Boy howdy your boyfriend sure did fuck 55-60 women in total over the course of his life." That's not going to happen. But worst case scenario, if someone does rat you out, tell her that you became a born again virgin back in 2018. If she questions why you didn't specify that at any point during the course of your 4-year relationship, gas light the shit out of her. Make her seem like the a horrible person for not recognizing your born again virginity. Quite frankly it's none of her business. Bitch. 

Dear John, 

I’m 28, single, and just started living alone in a 1 bedroom apartment. How do I go about meeting “hot singles in my area”? Is such an act even plausible or should I just hang it up and pledge abstinence for the remainder of my days? Both seem equally viable and rewarding at this point. Thanks in advance.

Tinder, Bumble, Hinge, the ads in the margins of PornHub.com. They all work. But you gotta pay for the premium. I know how lame that sounds, but the fucking dating apps know what they're doing. As soon as I bit the bullet and paid for Hinge premium I started getting way more matches and way more dates. Some I even had sex on. The Porn Hub "hot singles in your area" ads are a little different. I can't say I've ever utilized one, but I'm sure they work. Just give them whatever credit card information they ask for and soon enough you'll be knee deep in heavily diseased puss. 

Also on the dating apps, don't waste time with conversation. Say what's up, make an easy joke, maybe compliment her dog, then ask her to meet for drinks. Don't spend more than a few texts getting to know her over the phone. It took me and embarrassingly long to realize you just gotta set the date ASAP.