Back in September, I got the kind of invitation you don’t expect to actually happen. When I played Tobacco Road earlier this year, I met two new golf friends (Maryam and Darin) when I was paired with them as a single, as we wrapped up, casually said, “You should come play Pinehurst with us sometime. Maybe even No. 2.”

Most golfers know that line. People say it the same way you tell someone “We should grab lunch soon!” You mean it in spirit, but life usually gets in the way.

But something stuck with me when they said it. I remember thinking, I think they actually mean this. And sure enough, a few months later Darin and I were trading weekends to find a date. Ted (one of my closest friends and the guy who got me into golf years ago) joined me for the trip, and suddenly we had a full Pinehurst weekend planned.

We played Tot Hill Farm in Asheboro on Friday (another wild Mike Strantz track), Longleaf on Saturday, and then capped it off with Pinehurst No. 2 on Sunday afternoon.

Everything felt like a warm up to get ready for Sunday.

On Sunday in the early afternoon, we actually started on No. 10, a par five, to help pace of play. Even so, I had the same feeling I’d only felt once before: standing on the first tee at the Old Course at St Andrews. It’s that mix of adrenaline, history, intimidation, and gratitude all at once. 

But Pinehurst No. 2 felt different. It carries the weight of Donald Ross, Payne Stewart’s 1999 U.S. Open, and over a century of championship golf. There’s a sense that you’re not just playing a course, you’re experiencing the same obstacles golfers have played through since the 1890s.

Ted and I also got to play with a caddie (he was double-looping and carried both our bags). Having a caddie is totally optional at Pinehurst, Maryam and Darin didn’t use one and took a golf cart, but on No. 2, especially on those greens, he was worth every bit of the help he gave us. 

I’ll be honest, I didn’t drive the ball well all weekend, and No. 2 didn’t magically fix that for me. I think I hit maybe four or five fairways the entire round. But somehow, I scrambled out of my mind.

No. 2 is known for two things:

If you miss a fairway, you’re in sand, pine straw, wire grass, or some combination of all three (everything that looks like a bunker is technically a waste area, so grounding your club is allowed, although that doesn’t make the shot any easier).

On that opening No. 10 par five, I got up and down for par, and that settled me. I remember thinking, Okay. I can actually do this.

I ended up making five up-and-down pars on that first nine (a number I never come close to). Normally I might have one or two. Somehow everything clicked with the wedges and putter. I shot a 38 on that side (our first nine), finished on 18 right by the clubhouse, and was feeling way too confident for my own good.

And then we looped around to Hole 1 (our 10th) and Pinehurst No. 2 reminded me exactly who was in charge. Hint: it wasn’t me.

I hit a decent drive just off the fairway, caught the greenside bunker on the left, and then lived out the most stereotypical Pinehurst sequence:

Just like that, I was humbled. The course always wins these arguments. For an extra dose of humbling, Ted and I stood on a few tee boxes for the US Open - same course but 1,000 yards longer. 

Everything you’ve heard about these greens is true.

If you’re above the hole, you’re in trouble. If you’re putting downhill and down grain, you're barely tapping the ball and hoping. There’s no backstop. Everything runs away. The edges reject everything. The entire green surface feels slightly crowned. 

Our caddie helped a ton here. Reading the grain, spotting the fall lines, and telling us where not to miss was the biggest difference-maker of the day. That advice alone probably saved me five strokes.

When I kept the ball below the hole, I could putt with confidence. When I didn’t, things got fast and ugly quickly. Nothing made you feel helpless like putting downhill and with the grain of the grass. 

One of the best examples of my odd game that day was the 14th hole. I never touched the fairway. I hit this towering push-fade that landed on the 13th fairway. When weighing my options with the caddie, he reminded me two things: I had made 5 up-and-downs for par on the first nine holes, and that I didn’t come all the way to Pinehurst for conservative shots. Somehow I hit back over a set of tall pines, got it nearly off the green, chipped on, made par, and walked off shaking my head.

That was the story of the day: spray it, scramble, breathe.

Ted (of course) hit perfect drives all afternoon. Every group needs that guy to keep the confidence level average. Many times Ted took a look at my driver set up and said “are you sure about that?”

Pinehurst also has a fun tradition (if you make a 2 on Pinehurst No. 2, you get a “Deuce Coin”). We didn’t walk away with one, but we flirted with the idea a few times. On a couple par 3s we had real looks at birdie, and for a split second it felt like the coin was in play. Close… but not close enough.

What made the day special wasn’t just Pinehurst No. 2. It was playing with people who genuinely wanted us to experience it.

As we warmed up, Maryam and Darin were almost more excited than we were. They talked us through the course, told stories, pointed out details, and kept saying how pumped they were for us to get out there. That kind of hospitality sticks with you.

We also stopped by the World Golf Hall of Fame before the round. I’d been earlier in the summer, but walking through it before playing No. 2 hit differently. I felt like we were trying to squeeze the last bit of luck we could from the titans of golf. Maybe if I walked by the Tiger section one more time, I might get some swing improvement via osmosis. Seeing Payne Stewart’s legacy, the history of American golf, and then stepping outside into the village (where everything and everyone revolves around golf) felt surreal.

Pinehurst isn’t just a resort. It’s an entire town built around the game. Eleven courses (with No. 11 currently under construction), plus The Cradle. Thirty-eight total courses in the surrounding area. Even down to the collector (and complimentary) tees at the hotel, and clubhouse, and Pinehurst courses, everything is designed with golfers in mind.

As guests of members, Ted and I even got to see the members’ clubhouse and shop their member-logo gear (a pretty cool moment and something I’ll probably brag about for years).

If you’re thinking about taking on Pinehurst No. 2 someday, here are the things I wish someone had spelled out for me:

On the way out, I half-joked (but also fully meant it) when I told our hosts:

“Well… now I’ve got 10 more Pinehurst courses to play.”

Playing No. 2 was incredible, humbling, unforgettable, and something I’m extremely grateful for. It reminded me once again why I love this game: the shared experiences, the people you meet, the places this sport takes you, and the moments you talk about for years. 

And yes, I’ll be back.