Ask TSJ: Do I Gotta Fess Up?

LIFE IS HARD. It seems like every new day brings a new question that, try as you might, you’re just unable to find an answer for. The Smoking Jacket understands this, and we’re here to help. TSJ’s editor, Melissa Bull, and Headshots columnist, Mike Spry, set aside some time in their busy schedules to answer your questions in a feature we’ve cleverly named “Ask TSJ.

This week’s incredible question comes from a TSJ reader in Madison.

Dear Mike and Melissa,

Big fan, love your work. I’ve taken your (implied) advice a few times, and it has always worked for me. Now, I finally have a question, conundrum, concern of my own. I just met this girl, who I really really like. Problem is, I have a large group of girlfriends I still hangout with (and how some of she’s met) that I used to date/sleep with/make out with and I haven’t told the new girl. Is it too late to come clean? Should I just keep it a secret?

Please help,
Mark G. from Madison, WI.


Hey Mark G,

Here’s the deal. You don’t necessarily spill the beans all at once. Maybe New Girl doesn’t get off on that kind of thing. Picture it for a sec — is she supposed to listen to you drone on with your boring confessional list of ladies you’ve seen without their pants on? Is New Girl your priest? (Only say yes if she’s your naughty priest but don’t make me talk about it anymore because I don’t want to picture that.) Is she your bro? Is she gonna high-five you? “Man, that lady’s smokin! Nice score, Mark G!” Mmm… Probably negatory.

Here’s what I think. You woo the New Girlie. You enjoy the wooing. You chatty-chat, you drinky-drink, you hold hands some. Wooing is about you and she, in the beginning, with only vague allusions to the last ten to twenty years of your past. Right? Right.

But you’re a good guy and you don’t want to deceive her, and that’s swell of you. So what you do is at some point you drop your philosophy on exes, how important it is to be friends with them. How you don’t understand people who don’t do that because that’s really not friendly, that’s really not nice. How do you stop the love that once was there? How do you not keep the respect? You keep the respect like that! Yeah you do! That’s the kind of man you are. Paint yourself in a kind of saintly light like that.

Plus what’s the alternative? Would New Girlie rather you had never encountered lady love? No she would not.

That’s a fact.




This is a tough spot, because it could go either way. She could be impressed by your candor and honesty, or repulsed by your inability to have a platonic relationship with a woman, and as such be threatened by your “exes” presence.

So what then?

I would come clean. Tell her everything. Hell, if you have photos of you and one of these girls doubling up on a tranny midget bathed in margarine, I’d show her that too. Be fearless in your honesty. If she stays with you, you’ve found the one. If she bails, well, you’ve got a stable of friends with benefits waiting to console you.

It’s win-win. Except, you know, the second one is a loss, really.

Good luck,

Got a question for Melissa and Mike? CLICK HERE and fire away.
If we use it… your life will improve immediately. 

Related on The Smoking Jacket:
Who’s Hotter? Gillian Anderson or David Duchovny?
I Hired a Warlock to Bring Back My Ex, But–
Ask TSJ: Do I Got to Tell Her I’m Not Into Jesus?