Wooing The Barberess of Portsmouth

About being both smooth AF and awkward AF

Time To Read: 6 mins | April 30, 2017

I was trying to find a pub. And while that sentence accurately describes most of my mornings, I was particularly determined on this occasion because I’d walked by one earlier in the day that actually had sports playing on a high-def television above the bar. In my South American experience, this is a rarity. But after half an hour of failed searching, I dismissed the place as a hallucination. Like some sort of heavy drinker’s mirage.

So eventually, exhausted, I instead stopped in a cafe overlooking Valparaiso.


I operate on equal parts alcohol, caffeine, and happy thoughts, so in terms of fuel, coffee was just as useful as beer.

I was dozing off and admiring the view when the waitress walked over, who was both very cute and spoke perfect English. After 7 months of barely understanding what’s said around me, a girl’s ability to speak my native tongue has become a turn on.

I had a cappuccino and paid and left. Really, nothing interesting happened, so there’s no need to dwell on it. I knew I should have asked her out — there’d been lingering eye contact, a couple small laughs and, unusually for me, I didn’t break wind once — but I was tired, sober, and had a plan.

Which brings us to The Barberess of Portsmouth.

I didn’t name her that, a buddy did upon hearing this rollercoaster of a story. Frankly, ‘barberess’ is a bit too grand of a title for a 25-year old SuperCuts employee, but the name stuck, so what can you do.

This was back in 2007. I was working an internship in college & living outside Portsmouth, New Hampshire, which means I was near negative two points of interest for a kid my age. I was 20-years old in the middle of nowhere, with no friends for 100 miles in any direction. I watched a lot of Netflix without any chilling.

So going to a hair cuttery (definitely a word) was a big curveball in my routine. And lo and behold, after waiting in an uncomfortable chair for fifteen minutes while reading a two-year old Sports Illustrated, my name was eventually called by the only drop-dead gorgeous stylist in the state.

I was more than a little excited – you know that tarp they wrap around your neck to keep your hair off you? That goofy piece of plastic was key to hiding my half-pitched tent.

And much like my coffee server in Valparaiso, everything went well. We held eye contact a bit longer than necessary, had a few mutual laughs, and while I did lightly pass gas twice, neither actually smelled, which is the same as not farting at all.

Once again, I knew I should say something, but I didn’t. She was wearing a ring on that finger, and even though it didn’t look like a proper wedding band, my yellow side used it as an excuse to say nothing. I tipped too much and left in shame.

This bugged me for days. As much as I was loving the early seasons of Lost, you can only watch so much TV on your computer alone without feeling like you’re becoming this guy from South Park. Something needed to be done.

It was round about a week later when the loneliness reached critical mass. I don’t know what got into me – probably tequila – but I decided to swing for the fences.

I drove to the SuperCuts again and, sure enough, the Barberess was there. My heart was shaking harder than an overly aggressive vibrator as I opened the door, marched up to the counter, and asked to speak to… whatever her name was.

She walked over and I, with about as much smoothness as McLovin at the liquor store, asked, “Uhhhhdoyouwanttogooutsometime?”


The flamboyantly gay employee in the back of the room started bouncing in his chair and clapping when she, blushing, said yes.

I got her number and probably walked out far too quickly. There’s a line from Moneyball where Brad Pitt says, “When you get the answer you’re looking for, hang up.” Same concept here.

Now, if you thought this story was all self-aggrandizing and congratulatory, you were sorely mistaken. Because while I look pretty cool right now, this tale’s about to go the way of the Johnny Manzeil’s NFL career really fast.

I actually can’t even bear to fully flesh out how bad this evening went, so I’m just going to blast through it: I picked her up, made some accidentally insulting joke in the car, took her to Applebee’s (you can’t make that up), spilled a Coke on myself and didn’t play it cool at all, then still went for the kiss afterwards and was told, “Are you serious?”

The consequences of this evening were two-fold. First, it took about six months for me to brave a proper date again. Hindsight and a few asshole friends showed me the eighteen dozen ways I’d just made a colossal walnut of myself, and my confidence needed time to lick its wounds.

But more importantly, there was the realization that the Barberess should never have gone out with me in the first place. I was significantly younger than her and, frankly, she was out of my league. But she’d been impressed with an act of insane boldness and won over, at least momentarily, by brute force. This was a lesson that stuck.

So when I returned to the Valparaiso café the next day for the server’s number, there wasn’t any real fear of rejection. Especially since there’s no Applebee’s in Chile.


photo: overlooking the cerro alegre district of valparaiso, chile

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Malcolm Freberg
Malcolm Freberg
American writer living permanently on the road. Believes rye whiskey is superior to bourbon, Belle is the best Disney princess, and that selfie sticks should be snapped in half on sight. Hosted a travel documentary for AOL & played Survivor a few times.

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1 Comment

  1. Jess

    It took some major balls to pull that off, so I wouldn’t call that a failure. I love the way you write, painted the picture of your experience in my mind perfectly. I look forward to reading more of your content. PS. Lost is one of the best shows on Netflix 😉


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