It's probably true with everyone who's met a few major leaguers--the younger I was, the more memorable it was. Growing up in rural South Dakota there were very few opportunities to come face-to-face with a big-leaguer. Tony Oliva, Ron Coomer, and Marty Cordova had all made appearances signing autographs at the Huron Mall in the mid-90s, which was thrilling for me.
But the best was of course the Twins Caravan in 1999 when Kirby Puckett, LaTroy Hawkins, Doug Mientkiewicz, and John Gordon rolled into Huron for a dinner and Q&A at the Crossroads Hotel. I was a sophomore in high school and was supposed to have basketball practice that night but thanks to record wind gusts, practice was called early. I drove 45 miles into Huron all by myself and went to the Caravan event. During the Q&A, I raised my hand. I had just recovered from a broken leg that knocked me out of football that fall, and asked the players if anyone had ever experienced some sort of injury that had threatened their careers. Kirby, sitting right in front of me, had obviously had his career ended due to glaucoma, but he apparently didn't consider that an injury and passed the mic over to Doug, who gave a candid response and later came down and shook my hand and wished me well on my recovery.
Another memory that sticks out was in 2002, I was working a summer job at Valleyfair and my co-workers and I took in a Twins game after work on a random weeknight. After the game a few of us hung out by the players entrance, hoping to snag an autograph or two. David Ortiz signed a few autographs and took a few pictures, but just as he approached me he said "thanks, that's all for tonight." I called to Ortiz, "please, just one more picture?" He turned around and came back and took the picture with us.
Another time years later at TwinsFest, my then-fiancee and I met Kevin Slowey. I told Kevin some boring story about how I once knew someone else by the same name. Kevin was like "oh, huh." My fiancee laughed at my failed attempt at interesting conversation and said to me "You're very special today." Kevin thought the comment was directed towards him, and said "oh, uh... thanks." So we both felt like fools. As we were walking off the autograph platform, we went around a corner and my fiancee literally ran face-first into Paul Molitor.
At another TwinsFest a year later, my friends and I saw Bert Blyleven just standing by himself in the middle of several exhibits. We approached him for a picture, and he talked and talked and talked. He asked us all about ourselves. We were the ones who eventually broke up the chat and left! So strange.
There were countless other run-ins, though only a few times where it wasn't after a game, at TwinsFest, or the Twins Caravan. Now 34, I don't think I'd be very interested in meeting players my age or younger. There are a few legends I'd still like to get a photo with, like my all-time favorite, Jim Thome.