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

Q. Train, sweet column dude.  Right on with the farm league system of dating.  I’m wondering what your opinion is on the dreaded topic of the ex.  When is it legit to bring this up? – Biff Tannen, Hill Valley, CA

A. Ahh Biff, that’s a conundrum that has stood the test of time. There is always the past and learning about it can better prepare you for the future. This is like going to history class except your teacher isn’t some fat guy on tenure; it’s some beautiful babe you’re looking to bed. That is unless you’re on a date with my 10th grade history teacher, but I digress. So, when should you bring this up? Most will tell you to avoid it as much as possible; I say bring it up as early as the conversation will allow. Whether that’s the first date or the fifth, that has to be up to you, but let the conversation happen. I lean towards bringing it up early because the answer she gives will tell you a lot of information about the person. Certain things she says will tell you what she is looking for or what she has hiding in the proverbial “relationship closet”. So lets go through the answers so that this strange land of the relationship past becomes more familiar:

“I was with a guy for about 4 years and we broke up about a month ago.”

They’re probably still banging. You’re just the background noise to help take her mind off the Ex on a Saturday night. Hell, she’s probably going to the bathroom so she can sext him some emoticon they created together. You see, long-term relationships don’t just end on a set date. Like a killer from a horror film, they just…won’t…die. They need to be shot in the head like 5 or 6 times; and in this case the “shooting” is resentful, regretful, needy ex-sex which is then followed by tears of what could have been. What I’m saying is, don’t get too attached to the role, you’re just an understudy.

“I’ve never really had a long term boyfriend”

As the old saying goes: “Better to have loved and lost than never to have farted while in the same bed as your significant other.” (or something like that) There are things this person has never experienced and that isn’t good or bad but it’s something to remember. She has as little idea as you do about how the two of you will work in the future, and that is sort of thrilling but also a little dangerous. It can mean she has no expectations (thrilling), or completely unrealistic expectations (dangerous). Keep an eye on this one; you don’t want to end up as this person’s emotional chemistry set.

“I don’t want to talk about that a$$ho((”

Yikes. She’s bitter, she has trust issues, and – oh yeah – she’s still in love with him. Move on before she starts asking you “what your intentions are” like some dad from the 1950’s.

“I was with this guy for a while in college and now we are like best friends”

Ehh, I don’t necessarily have a problem with this, per se. Chances are, though, this means that they are ‘best friends’ because the guy is still in love with her. I mean, this is like the premise of every romantic comedy ever made. You’ve got to have a lot of confidence to deal with this, because he is going to be around – lurking, stalking, planning; waiting for you to spend a little too much at a strip club one night so he can be that one tearful phone call she makes on a rainy Friday night.  Then he swoops in to have resentful, regretful, needy ex-sex after a shared pint of Chubby Hubby.  Be ever vigilant. I’ve been broken up with and ended plenty of relationships with the line “I hope we can just be friends” and I’ve never hung out to watch an episode of “Grey’s” with them on a Sunday. I’m just saying, lets be real here.

“He would get jealous all of the time and I just want to have fun.”

Not ready to be in any type of relationship and really doesn’t care about it. ‘Fun’ means getting free drinks at the club while dancing on some Ed Hardy mannequin. I’m not judging at all, good for her – just not relationship material. So go ahead and order her another Apple-tini and bring the ‘fun’ to your place.

“A few here and there but nothing crazy; I’ve been with nice guys, and I’m happy now.”

The confidence, experience, and the happiness that comes from understanding that not every relationship ends with a winner and a loser; that not every relationship is a fairy tale – they’re far more subtle, interesting and meaningful than that, even if they don’t work out. This is the answer you’re looking for.

If you know what you’re looking for, these answers give you a lot of insight to what this person’s “deal’ is. There is a wild card in all of this: you. If you don’t have the confidence to process the idea that she has very likely had relationships (read: sex) with several people before you, you’re probably not ready for a relationship yourself. That means it’s time to spend a little more time with your other girlfriends: Rosie Palm and her five friends, so that you can at least get your rocks off while you adjust. Let the question grow organically from conversation because you’re genuinely interested in the type of person she is. The ‘dreaded topic’ shouldn’t be ‘dreaded’ unless you have something to hide. And if you’re going to be analyzing her answers, take a little time and analyze your own. Unless you’re just looking to get strange…then don’t worry about it.

You’re welcome,


Do you have dating questions for J-Train? … Email me!

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