Pull The Trigger On A Random Trip Before It’s Too Late

Pull The Trigger On A Random Trip Before It's Too Late

Your window could be closing. Hell, it may already be closed.

Mine is closing, and I’m fine with it. I had my fun, but for many, the clock may be running out for you to pull off the random, spur-of-the-moment New Orleans, Vegas, Memphis, Nashville, where the fuck ever trip with your boys/girls/squad/team/clique.

Here’s the way it is: From 22-25, assuming you have the means or just don’t give a damn about fiscal responsibility, you can pretty much convince your friends to do anything. Bourbon Street for NYE? Book it. You need this. They need this. Everyone’s probably single and gutting it out on the bar scene and fumbling through whatever app is en vogue. It’s tough getting laid in a major metropolitan area where everyone looks and acts like they’re living off of a massive trust fund, and that reality is humbling. A quick change of scenery will be viewed as a godsend. You send out the email, and within 10 minutes, you see this:


Followed by:

Good call. In.

Then probably this:

Just booked.

Sure, you’ll have the outlier who married his college sweetheart immediately after graduation, or the person who took on a mountain of debt to keep living the dream by going to law school, and they probably won’t be in attendance. But this window is your best shot at getting the band back together for another tour. At this age, you’re probably able to go hard back-to-back with no recovery issues, so there’s no need to take Monday off to sit at home and lick your wounds while watching The Price Is Right. Very doable.

Then it gets dicey. The infamous 26-29 range is filled with obstacles and variables that you just can’t plan for. Let’s say you’re the unmarried quintessential young professional, and it’s been well over a year since the gang has been back together raising hell and making memories. It hits you. You’ll get everyone to make the trek to homecoming in the fall, and all will be right with the world. You put together a fire email filled with anecdotes from years past, and pics of the damage that was done the last time everyone got together. You hit send, and the thought of this trip has you walking a little taller and feeling pretty damn good about yourself.

Then you wait.

A few hours later, you get your first response.

I’d be in, but we’ve got a wedding that weekend.

Okay, not the start you wanted, but it’s just one person.

We’ve got a trial the week after, but if it settles before, I’m in.

Uh, okay. That’s better than “no.”


That’s what you were looking for. Get the mo’ back on your side.

So in.

Here we go. So what if it’s your sleaziest friends? It’ll still be a good time.

At stage of your life, you can still pull these things off, but making it happen is an art form. Once 26 rolls around, the competition really gets taken to the next level. By now, at least two of your good friends are married, and there’s no chance you’ll be able to snag both of them for something like this. Sure, they could, in theory, bring along the ball and chain, but that means they’ll have to book another flight and a separate hotel room. Shit’s not cheap.

And of course, you’re going to be competing with the wedding circuit. Go ahead and assume that half of the people you want to go hard with will be unable to attend because of showers, engagement parties, and weddings. Get ready for “Ahhh, we’re traveling a lot in October and we just can’t pull it off,” and probably a few “I need to see if I can get the Monday after off, first.”

Now, this doesn’t mean that it’s not worth doing. While you’ll be limited in quantity, the quality of the cast will lend itself to the heathens that you really want to go hard in the paint with. If you’re able to pull off a coup and land one of your married friends, chances are they’ll end up being the MVP of the weekend. It’s doable, but expect some last minute back outs.

30? Couples’ trip, if anything. If you’re married, book two flights. If you’re dating someone, you can either let that person know how little you care for them by not inviting them, or you can bring them along and take the thing up a notch. Those are your only two options. Doable? Kinda. I guess. Fuck.

So, what’s your move? You have to sell. You can’t just fire off some mailed-in email or text with “Anyone wanna do a Vegas trip in the spring?” Nah, man. You need passion. You have to be Billy Riggins when he’s trying to pump Luke up after Luke shows up drunk to his house looking for Becky. You need to sell the trip. Convince them that they need it. Be aggressive. Use salty language. Get in someone’s face (via email).

Here’s an exec move for you: Build a coalition before sending the email. Put in a few calls to some key players in the group. Get them on board, and then send out the email. Make sure they’re the first to respond, because the snowball effect is real. And if you’re not afraid to roll the dice a little bit, book your trip. It’s bold and wildly irresponsible, but they’ll respect you for it. If they’re your real friends, they’ll find a way to make it happen. They can’t just let you go to Vegas alone for 48 hours, right?

What’s the takeaway from this? Go book a trip. That’s it. Break out of the rut you’re in and put something together. Stop right now and ask yourself whether you have something to look forward to in 2016? If yes, then I salute you. But if you don’t? Go do something about it.

Image via f11photo /

Email this to a friend


Lawyer. Writer. Dude doing business. I'm the meatloaf guy from tv.

15 Comments You must log in to comment, or create an account
Show Comments

For More Photos and Content

Latest podcasts

Download Our App

Take PGP with you. Get

New Stories

Load More