Adventures in Road Tripping Part 4: All Good Things Must Come to an End…or a Temporary Pause

As we rolled into San Diego on a sunny Sunday afternoon, depression started to set in. In less than 24 hours I was supposed to be boarding my flight back to Chicago and trading 80-degree temps for 50’s and rain. Determined not to let the inevitable (me leaving) get us down, we headed for Balboa Park to stretch our legs and let Baker make some friends at the dog park before checking into our amazing last-minute AirBNB booking at the Granada House (make sure to check out their blog too!!) in San Diego’s North Park neighborhood. As our stomachs began to growl (yes, gays really do eat sometimes), we set off for the beach to grab dinner and catch the end of the sunset.

SD Sunset 1

I mean seriously…how can you not fall in love with this view?

And just like that, my love affair with San Diego began.

After a delicious dinner of fresh seafood-centric tapas, we headed back to the Granada House to rest up. There was no such thing as spending too much in the Great Outdoors for us – especially since my time in California was quickly nearing its expiration date. In less than 24 hours I was going to be heading back to Chicago so we figured we may as well get in one last good early-morning hike in the sun to intensify the tan lines and ensure envious stares of jealousy of my non-fake-bake-acquired glow.

As we left the city the next morning with the windows rolled down and volume cranked up, I started thinking to myself “Wow…I could totally see myself living out here. I wish I didn’t have to head to the airport this afternoon.” After a quick discussion with my co-pilot about what all else we wished we could do but couldn’t because I had a post-hike flight to catch, I made up my mind. I was not going back to Chicago that afternoon.

Before I knew even it I had dialed United’s customer service line and was explaining to the girl on the other end that there was just absolutely no way even remotely possible that I’d be able to make it to the airport in time for my flight that afternoon due to “unexpected circumstances” that we’d run into on our road trip. It just wasn’t going to be able to happen, and was there anything I could possibly do to change my flight? Could I move it to Tuesday or Wednesday perhaps?

Why yes. Yes, I most certainly could.

For one easy payment of $75 I could reschedule my flight for Tuesday.

But even better yet? The option to move it to Wednesday for only $100. All things considered, since I’d booked my original ticket for about $56 thanks to some frequent flier miles (thanks mom!), paying $100 to change my flight and be able to spend another two days in California was a bargain. I was sold.

I finished up on the phone right as we arrived at Mount Woodson. Perfect timing. Bring on the tan lines.

SIDE NOTE: Never before had I been more excited to actually have tan lines. I’m always one for having none at all, but when in Rome… (or California in this case)

Mount WoodsonMount WoodsonMount WoodsonAs we hiked up the hillside (on a thankfully well-maintained access road nonetheless), my friend mentioned that – after mastering this – we should do a nearby 14-mile hike….while I was sweating my ass off and running out of water. Over my dead body.

But okay…fine. I agreed and told him we could do this – but it would have to wait until the next time I visited.

As we got to the top I realized why my friend had kept telling me to keep walking. The view from the top was in-freaking-sane. Talk about absolutely breathtaking. Who would’ve guessed that there were cities where, on pretty much any given day out of the year, you could drive 10 minutes or less and be on the beach then randomly decide “Hey, I feel like going hiking today!” and hop in your car, drive less than 30 minutes, and be hiking in the mountains? Hello, paradise! I could totally get used to this.

On our way back down, we ran into a girl who asked if she was going the right way to get to something called Potato Chip Rock. We’d never heard of it and had no idea, but after Google’ing it and discovering it was close by, we added it to our list of must-see’s for our next hike. Our bucket list was quickly growing at a rate so fast that I’d probably need to plan on moving to San Diego in order to feasibly accomplish everything by the end of my lifetime.

Later that afternoon, we headed to the dog beach to give Baker a chance to run around (as if she wasn’t worn out enough from our hike) and make some new friends. Of course, being a size-queen-in-training, she would choose only to make friends with the biggest dogs possible – in particular a Great Dane. Leave it to her. Like father (and uncle) like daughter. We couldn’t have been more proud of our little princess.

As we left the beach that afternoon, reality started to set in: sure, I was leaving in two days, but my friend still didn’t have an apartment lined up. While the weather was great, and he had a car that he could technically live out of (or a tent!), it really wouldn’t be ideal to do with a dog. He had plans in the works to find a place together with another friend of ours who’d been subletting a room from some whackjob he’d found on Craigslist, but they couldn’t seem to come to an agreement on a neighborhood/price/apartment/anything, and time was running out before we’d be homeless.

But just like that…he got a text that our friend had found a place with serious potential in Hillcrest….so off to Hillcrest we went – and like some cheesy Lifetime movie, it was love at first sight. The apartment was perfect. A few phone calls and emails later, the application was filed. It was time to wait, and what better way to pass the time than with cocktails – and karaoke of course. Hopefully it would be better in San Diego than in Portland. Little did we know, we were in for a treat.

That night, we headed out to a few of the gay bars in San Diego – one of which, Flicks, touts itself as being the place “where you go in Hillcrest to meet people of all ages and backgrounds, make new friends, play pool, share common interests, and just…well…hang out, have a drink, and have fun.” Plus they had karaoke on Monday nights. This was our kind of place.

Well, well, well….

By 11:30pm not only had we been accused of having sticky fingers and jacking some guy’s new iPhone 6 (because heaven forbid someone else have the same phone that just came out as you do) that he lost, but we’d also had a caricature drawn by a homeless-looking man who offered it to us in exchange for a few dollars or a drink.

994642_10107245714012924_8767479761013005466_nBetter yet though – and probably the highlight of the entire night – was karaoke. Sure, one girl totally shut it down with a perfect rendition of “Let It Go” from Frozen, but the host of karaoke stole the show. After proceeding to get sufficiently shitfaced (before 11:30pm nonetheless), she wiped out and consequently capsized the DJ booth on her way down. No joke.

While watching her be force-fed bottled water and escorted off stage by security, we decided that we’d found a new favorite bar. Nothing says “Typical Monday” like a drunken karaoke host falling off the stage. We were officially sold on Flicks.

Tuesday morning, we headed to Snooze for brunch – one of my friend’s favorites with delicious food, great service, and a fun retro vibe (that reminded me a lot of one of my favorite bars back in Lincoln, Nebraska called The Starlite Lounge) – before heading to pick up keys to the apartment. That’s right…we’d gotten a call that they’d been approved and could start moving in that day! Cheers to not being homeless!

That night, we headed back out to celebrate. Since it was my last night in town, it became a bit of a blur pretty quickly (but I’m not one to complain).

Wednesday morning, I didn’t want to get out of bed. I was full of so many mixed feelings. Sure, some of them were “I feel like I’m going to die…I’m never drinking again” types of feelings from the night before, but more-so feelings of “I can’t believe it’s over” and “I really don’t want to go back to Chicago.” I’d officially fallen in love with San Diego.

What did I have waiting for me in Chicago? Sure, I had friends to go back to. But a career? Real estate? A relationship? No, no, and no. There was really nothing keeping me rooted in Chicago except a service industry job (SEE ALSO: America’s New Favorite Reality Show: “My Job Is An Absolute Joke”) that I loathed – and have since quit. Why couldn’t I just stay in San Diego and have my belongings shipped out to me? Why couldn’t I just find a new job in California?

As I stood in the shower sobering up, I kept asking myself “Is going back to Chicago the right thing to do? Why not take a total leap of faith and start fresh in San Diego?”

Even as I arrived at the airport, I didn’t know what I was doing. With an offer on the table to stay with my friends until I found a new job, figured out where I’d be living, and bought a car again, it was a tough decision. Stay? Go? Come back?

As I choked back tears and said “I’ll see you soon” as my friend dropped me off, I knew we’d bonded more tightly in the past two and a half weeks than I’d had with some friends I’d known for 20+ years. I made up my mind that I’d be back. San Diego was where I wanted to be. My OCD self just wouldn’t let me allow someone else to pack my entire life into boxes for me.

So with that, we parted ways and I headed back to the Windy City with my mind made up: I’d be back sooner rather than later. While all good things must come to an end, this was only a temporary pause. The road trip of a lifetime may have come to an end, but the adventure was only beginning.

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