Our Day Trip in Milwaukee

It started as a driving tour... but it got WAY BETTER!

There we sat feeling especially covert in the glow of Safe House’s bar. Sipping on our martinis (shaken, of course), nibbling suspiciously on our french fries (they are French, after all) and eavesdropping like old pros. We were already enjoying our walking tour of Milwaukee. But, thanks to the open seats to my left at the bar, the day would prove to be one of the best of the trip.

As we were finishing up, two good-looking strangers strolled up to the bar next to us and asked if the seats were taken. I wasn’t sure what the correct answer was, and since Victoria was still on line with an informant (or her mom), I was on my own. I insecurely said “no, please sit” and shifted my stool slightly to the right.

We struck up a conversation with Conrad and Lori, quickly learning that he, a native of Cream City, was showing Lori around the town, and knew she just had to see the Safe House, or as the locals refer to it “International Exports, Ltd.” They work together at a cruise planner that schedules exclusive 16-day train excursions out West, and had only recently struck up a relationship.

They are quite the couple – attractive, outgoing, with interesting individual histories, and a shared lust for life’s experiences. Both were quite youthful looking and always ready for a laugh, it was hard to see them as our senior. In fact, they looked and acted like teenagers in love.

Though separated by a full generation, and two decades of life, there was an immediate connection. And soon we found ourselves touring the city with Conrad as our guide.

It began with a quick search for his Subaru, but turned into a “check this out”, “here’s some history on this” and a comparison of our shared wealth of useless knowledge. Conrad explained that he spent some time on the Milwaukee Police force and knew these streets like the back of his hand. And thanks to this, combined with his experience as a tour manager, we couldn’t have paid for a better driving tour.

Following the driving tour, he took us to see and meet many of his old friends and favorite hangouts. First Barnacle Bud’s for Corona’s, then on to the Mexican restaurant La Fuente for some fresh guacamole and burritos, then on to Gillis Frozen Custard (LINK: http://www.gillesfrozencustard.com/) for what he described as the best custard in the world. Of course Conrad picked up the bill at Barnacle’s and Gillis and Lori the check at La Fuente – what great people.

Next, as the sun was beginning its descent, Conrad suggested – though we were all filled to the brim with about 42,000 calories of Milwaukee’s best food each – that we swing by the grocery and grab some authentic Milwaukee brats, a few kabobs and some more beer and swing back to his place for a barbeque. On the way, we stopped at a gas station, and you guessed it Conrad stopped in to say hello to the clerk and decided to pay for my gas, and then he paid for all the groceries, not even letting us consider paying for any of it!

This is where the story goes astray emotionally for me. I wasn’t really sure how to accept these strangers’ generosity. As travelers, we have to remain very guarded for safety’s sake on the road and sometimes it’s difficult to put that barrier down to truly accept someone’s honest hospitality, or even to believe that their honest hospitality is just that and not some scheme to rope you into something you didn’t see coming.

I would consider myself an above-average writer, and I’ve written three dozen or more articles since the day we met Conrad and Lori, but this particular journal entry has eluded me.

As the day went on, their generosity grew – from the gasoline to the groceries – and I didn’t know how to react.

Maybe it’s society, maybe it’s my upbringing, but it seems I always look suspiciously at anyone who goes above and beyond to help someone, I kept thinking about all the times a free lunch meant sitting through intolerable Amway pitches from people who just missed me and wanted to reconnect.

“Hey Kimmer nice to see you – oh no this is on me – can I tell you about a way to make a ton of money, let me pull out this flip chart.”

While everything he did seemed genuine, I just kept feeling I needed to keep us at the arm’s length. On the way home from our day, Victoria was estatic, so happy to have met them and I felt like a heel. There was no pitch, no expectation from Lori and Conrad. A genuine friendship was on the table, and all we all we had to do was say thank you.

We learned a valuable lesson: keep your guard up – but leave your heart open and you’ll find the best experiences you could imagine right at your fingertips.

Just yesterday I sent Conrad a note explaining all of this and how much I struggled with this column. Of course, he understood and I can only hope we run into him and Lori on our later travels.