Everyone's Wingman: The Show Goes On!

“I want to surprise my girlfriend with a trip this summer. Somewhere fun and not obvious. Any thoughts?”

Nice job in planning this far in advance. For that alone, you have already one-upped most.

Cannon Beach, Oregon has beaches, lush forests, fine dining, and a stellar art scene.

Or maybe she’d prefer horseback riding on the beaches of Amelia Island, Florida.

Have you considered New Orleans? Sure, it gets humid as all hell. But don’t underestimate how romantic live jazz can be while you hold hands, maybe slow dance, pausing only momentarily to take a sip of your Old Fashioned. Man, that sounds great actually. Right? Wish I could do some shit like that. I’ve got so many issues from my Dad. Always thought I’d end up treating my girl the way he treated my mom. Never wanted to put someone through that. Never wanted to see myself become him, so I’d sabotage any promise of a real, functioning relationship. That’s been going on for, like, 8 or 9 years now. Damn.

What were we talking about again? Oh yeah, your fuckin’ trip. I don’t know, dude. Go rent some bikes and have a fucking picnic at a light house in Cape Cod or some shit. This entire entry is now just reminding me of how crushingly lonely I am with no one to blame but myself. I’m not my dad. At his lowest moments, he wasn’t showing me what I would inevitably become. He was challenging me to be better. Damn.

I ruined great things with amazing women, too. I’m talking dime pieces, brother. Smart and sophisticated, sure. But dimes.

Also, also, while I have you here: start tracking flights on Google. Enter your destination and dates, then toggle “Track Flights” on. You’ll get notified when prices drop. Save yourself some money and use that to upgrade your hotel suite or book a couple’s massage. Regardless, save up enough cash. A wise friend of mine once said that being broke and in a relationship were synonymous. Good luck in proving him wrong!

This was the sixth installment in an unwanted, ongoing series where I answer reader-submitted questions.

If you’d like to waste time at work while still looking productive, you can check out the other entries here:

Everyone's Wingman I: Tipping, Bar Etiquette, and Business

Everyone's Wingman II: Fashion, Bread-Winnin', and Someone Thinking You're Gay

Everyone's Wingman III: Running Late, Booty Calls, & "Just Friends"

Everyone’s Wingman IV: How Can I Tell the Same Story Over and Over without Upsetting My Wife?

Everyone’s Wingman V: Seasonal Depression: It’s About to Get Real Dark in This Bitch

Of course, you can always submit a question and finally stop getting in the way of me helping you help me help you. Just don’t ask me for financial advice. I will bankrupt you.