Notes on giving a “best man” toast

two brothers drinking Guinness
Raising a glass in 2019

This week’s article will be a little different.

Over the weekend I gave a toast for my brother’s wedding.

It is a writing project I had a lot of fun with.

I’ll share with you some general themes I was going for that I think are translatable to if/when you have to give a toast some day. If you feel inclined, you can find the full speech below.


  • As my father-in-law says: go for levity & brevity. I wanted to keep it short & punchy.
  • Remember the goal of the speech is to honor the person you are toasting to.
  • Plan & practice ahead of time.
    • I started jotting ideas down 6 months ahead of time. The speech has changed many times since. I only started practicing consistently 2 weeks out.
  • Story driven! I personally love when there are fun anecdotes, so I tried to weave a few in.
  • Fit the mood.
    • My family roasts each other, so I wanted to include a small roast for laughs – but do so in a way that still lifts my brother up.
  • Memorize or bring up cards for reminders.
    • This will keep the speech more interactive if you aren’t reading the whole time.
  • Eye-brain connection.
    • One of the “tricks” I learned years ago is to make eye contact with different people in the room. This helps you stay poised.

The Toast 🍻

Katelyn, we are thrilled to have you in the Connelly family.

The truth is, I had a feeling Katelyn would be joining our family someday after she survived a week, in a minivan, with my family on a vacation to Ireland in 2019.

The amount of banter she endured in that tight space was heroic.

Brian is three years my senior. Not so old that it felt like a huge gap growing up, but old enough that he was better than me at everything.

Brian wasn’t just my best friend. He was the toughest, fastest, coolest guy I knew.

In my eyes, Brian’s legendary toughness began in 2004. Early on that summer, Brian got beat up at the pool by a bully, named (pause) Brian LaValle (point to LaValle)…Brian Connelly asked for a pull-up bar for his birthday in August and started cranking out pull-ups until he could take on the rival Brian before the school year started. He went into the 7th grade that year as a hero.

The legend grew taller in 2006. I was playing wallball at Memorial Park and got into a scuffle with an older kid. Brian caught wind of this at the carousel. You remember the Carousel, down on Kinderkamack Road, where you would go to buy your tic-tacs and Gatorade, and maybe the occasional sunflower seeds. Yea, so Brian was chowing down on sunflower seeds with his boys when he heard that I got into a scuffle at the park with an older kid – and he immediately biked over there to pummel my adversary. By the time Brian Connelly got there, I was gone…but the story goes that Brian jumped off his bike without hitting the brakes and fed this guy some knuckle sandwiches.

By the time I got to high school, Brian’s reputation preceded me. He was so tough, people mistakenly thought I was tough. As many of the parent’s who new me as a child in the room can attest, I was a huge crybaby.

To a 14-year-old me, Brian was the closest thing I knew to Russel Crowe, fighting’ round the world.

I could go on, but I also mentioned he was fast. Brian held the pool record for backstroke at some point, and he was also the first person ever to defeat Uncle Jim in a foot race.

There was also the tricycle incident of 1998, year of the Denise.

We would sometimes race our little tricycles down a small slope in our backyard, which Brian got the big wheel on and I got some rinky-dink tricycle. Anyway, I won exactly one time…Brian let me so he could crash into me, which lodged me and my tricycle under the chain-link fence. I was then trapped underneath like my body was in a Chinese finger trap. When Brian tried to pull me out by my hands it would only get tighter on my waist. When grandma Connelly came outside Brian fled the scene…the only time I’ve seen true fear in his eyes.

I’ll cut the silly stories there, but there are 100s of them. I tell you these tales to underscore that for half my life Brian was one of my heroes.

Having Brian as an older brother was one of the greatest blessings of my life. I felt like the coolest kid on in the world when I got to hang out with the guys in our basement. I had someone I could trust who looked out for me. I could also observe how he blazed the trail ahead of me and got to learn from his successes and failures.

Speaking of failures.

Every hero has to go through the desert. My hero is no different.

The B-Man entered the desert after college. After graduating overweight Brian proceeded to bounce around different odd jobs. Things like drywalling, delivering pizza…the list is long so I won’t linger here.

All the while, he never complained.

The most distinct memory I have of my father from my childhood is the sound of his boots walking up the back steps at night. Always showing up. As reliable as the sun rising in the sky.

That’s what I think of with Brian finding his way through his desert. Consistent. Showing up. Channeling that can-do attitude and persistent work ethic we saw through our father growing up.

Brian found his way. Eventually getting trained as an engineer in the Army Reserves. Something he excels with to this day, even recently getting another promotion.

Let’s get back to Brian & Katelyn.

When Katelyn came into the picture I had to do some detective work. I needed a person on the inside who could give me the scoop.

So I arranged a meet-up, under the guise of attending a Shillelagh Law concert at Ulysses. There I met Sean Boland at the bar, slid him a Guinness, and said to Sean:

“Sean, you’ve known Katelyn a long time – what do you think of her?”

This is a direct quote, “Katelyn, oh, she’s solid”

After getting to know Katelyn over the last several years I tend to agree. She’s solid.

She brings enthusiasm and positive energy to all situations, is famous for her thoughtful gifts, and willingly comes to stay in a motel with us every year summer.

Most importantly, she makes my brother happy.

Brian, I’m so proud to have you as a brother.

I love you both.

Let’s raise a glass to the newlyweds.

Cheers to Brian & Katelyn! 🍻

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