DUDE DATING WITH J-TRAIN: AWKWARD MOMENTS

The J-Train is coming through and he’s got the dating advice you need!
From the long line of WWN advice columns (i.e. Dear Dotti, Ask a Chimp, etc) comes a new breed of intrepid advice giver. It’s Jared Freid aka J-Train. A frequent dater and lover…..
Dude Dating with J-Train: Awkward Moments
Q. I went on a nice date with a girl and we get to the end and I go in for the kiss and she goes in for the hug. It was about as awkward an ending as I could imagine having. The date was fun; we did drinks on a Wednesday, and had some great conversation. I would go out again but I feel like I blew it. What’s my next move? – Ralph Kramden, Brooklyn, NY
In football there are Quarterbacks described as “game managers”. They don’t go for the long throw; they just try and keep the chains moving by “taking what the defense gives them”. You, on the other hand, tried to fire a deep ball into heavy coverage. And you are no Tom Brady. I know our good friend in our pants tells us, “Hey! You just bought her drinks! She laughed at our jokes! And we deserve to get tugged.”  But your penis is lying to you; the penis is a selfish creature, a childish moron – it lacks socialization, or, for that matter, a conscience – and his thoughts and desires, if unchecked, will become your own. Your brain is the Quarterback and your Penis is a selfish Wide Receiver who only wants to get his and doesn’t care whether the team wins or loses.
I know this situation you landed in was embarrassing, but it’s not totally your fault – you had a moment of weakness, where all the insane ramblings of your dick started to make sense to you (he’s a persistent little bastard, isn’t he?). Fight the desire to mope about it, go home and masturbate just to shut that idiot up and send a quick follow up text to your date; something like – “Hey, I had a great time tonight. Maybe we could do it again some time, and I promise I’ll stick with the hugs, not drugs.” A text like that shows that you aren’t completely oblivious to how humans socialize (and let’s her know that sex isn’t your only goal), you’re willing to shake it off, and puts the ball in her court. If she wants to go out again, she’ll get back to you. If she doesn’t, then the next time you go on a date remember that your brain is the Quarterback and tell your P that you’ll get him his whether it involves this girl or your hand.
Q. I’ve been dating this girl and we’ve been having some consistently good lovemaking sessions. I want to get a little kinky but I don’t know how to bring it up. How would you get weird? – Barney Fife, Mayberry, NC
You need to plan for a moment like this like you would plan a bank heist; it’s all about timing. Two weeks before you bring up “the weird” you need to casually bring up a story about your friend and his fiance – set the scene with a couple that you guys barely even see but someone your lady has maybe met once or twice. The story has to be weird – like crazy weird, like so weird that its sheer weirdness chills both of you to the bone, and conjures the darkest memories of lived-through fears and regrets; so weird that both of you can only sort of laugh when it’s mentioned, the kind of laugh that trails off and leaves you with a single quiet moment where you both realize that only death could bring the kind of silence needed to forget this. Anyway, The trick here is you need to tell the girl your dating that your friend’s bride-to-be brought the whole thing up. Now wait two weeks. Don’t mention it; just let the thought of your friend’s weird ‘Texas Chainsaw Massacre-style’ sex stew with her every day; you’ve inserted a tiny idea in her brain that she can’t shake. She’ll wake up in cold sweats just thinking about it. She’ll have to tell her “besty”, her friends at work, and at some point she’ll randomly bring it up. Like – “I just can’t believe Suzy does that! It’s so weird, I just never even thought about her being like that.” Your response should be calm but agreeable to how freaky Suzy and Ron can get, like, “I hear you, but it’s between two loving people, so I’m OK with it.”
Now two weeks later you bring up whatever weird move you’re looking to do. Your lady has spent two weeks thinking about how crazy Ron and Suzy are, and is now thinking, “If there are people like that in the world, am I crazy enough?” Compared to your friends, your sex swing idea really isn’t so strange – tame even; a simple game. Also, remember how in the story, it was your “engaged friends” who get crazy? Even if she has reservations about your attempt at weird, she’ll say, “well, Suzy does that even weirder thing and she still got a ring out of it, so why not”.
You’ll thank me when your balls deep in chili sauce and she’s wearing that Bear mask you always thought was kinda hot.
Q. This chick and I are naked. We’re dancing around my apartment like two Native Americans praying for rain. Things are great, this is fun, when all of the sudden her thumb is knuckle deep in my butt. I let things play out and now I’m not sure how to feel about it. I feel a little bit turned on, a little bit turned off, and a little bit violated. Also, now she has been doing this regularly and I don’t want to make things awkward. What do I do? – Louie DePalma, NY, NY
Stop being so straight. If you don’t want a thumb in one of your orifices every now and again then move to the rural Midwest, buy a farm, get married, and have a few dozen kids that can help with chores like milking Bessie. If you’re in the dating scene then things are going to be weird probably more times then they will be normal. I went on a date with a girl who wore a Beret the whole time – not a mention of France, the arts, or even Beret fashion making a comeback. Seriously, a beret. It just sat there on her head as she sipped a mai-tai(!?). I didn’t ask any questions because I wanted to see where this was gonna go.
Sure, her thumb being used like some sort of butt pacifier is weird, and a little off putting, but with every thumb in the butt comes a message. That message being: “I like to get crazy.” You’ve been doing your Rain Dance and that’s been fun but now its time to push the limit. She probably likes some butt stuff herself and is just trying to push you into playing some “monkey see, monkey goes for more than two fingers.”
If you need answers then just know this – you run the risk of scaring her away. She certainly doesn’t want to face her weird fetishes in the cold light of day. Let her live her dark fantasies and strap yourself in for the ride.
You may be wondering how things ended up with the beret girl, turns out she was bald, only at the top of her head, like a monk. I never would have found out that the top of the scalp is so delightfully soft. Now every time I see Doctor Phil’s beautiful dome, I get a chubby.
You’re Welcome,
Train.
 
 
Do you have dating questions for J-Train? … Email me!
Follow J-Train on Twitter … http://twitter.com/#!/jtrain5