Arugably the hardest job of the groom: picking between best friends. Some tie-breaking solutions...

First of all, love the site. I was just reading your article Drafting Your Team which right now is my biggest concern. We both have a lot of friends and are looking at up to 8 people on each side.  That being said, I STILL am having a tough time deciding on 8.  I probably have 12 people I would consider and could probably narrow that down to 10 easily without feeling regret, but then the last two cuts are what are getting me. The shortest amount of time I've known any of them too is like 8 years so they are all old friends, some go back 15-20 years. Any advice on this scenario?

You're right. It's not easy. It's rare in life that you're forced to make an explicit, public declaration that identifies your "best friends," and it's uncomfortable for everyone involved (except, I suppose, the guys you choose.)

And, for that matter, this problem has grown worse over time. In the old days, when grooms married at the average age of 21, you probably only had 3 or 4 really best-best friends. Now? If you're getting married at 35, say, chances are you have your best buds from high school, your best buds from college, your best buds from the first city you lived in out of college, and your best buds from where you live now. (This is my scenario, by the way.) Thanks to the growth of email, texting, Facebook, and fantasy football, our best friends tend to stay our best friends...so we accumulate more and more--without losing many--and suddenly you're stuck with 12.

This is a good problem to have. But it can be a bitch when you're picking your groomsmen.

You have 3 different ways to go:

1) Consider lowering your number of groomsmen, not raising it.

Counter-intuitive, yes, but hear us out. If you have 8 groomsmen, then Best Friends 9-12 might think to themselves, "Daaaaaammmn. I thought we were lifelong best friends, and I didn't even crack the top 8? Jesus." If you only have three groomsmen, on the other hand, then that's an easier pill to swallow.

If you go this route, another way to make it feel more objective is to appoint "ambassadors" from each era of friend-hood. So you can have three groomsmen: one from your high school era, one from the college era, and one from the current era (just as an example.)  

To make it feel even more objective? Think about choosing the friends who are not married. That way, you can argue (even if it's only in jest) that your groomsmen should be the guys who still have a chance of getting lucky at the wedding.

2) Use 8 groomsmen, and then make the other 2 ushers.

Hell, if necessary, you could even have 4 ushers. (It's been done.) Think of ushers as like Assistant Coaches in the NBA; they don't count against the salary cap, so if you're an owner with cash to burn, like Mark Cuban, why not have as many as possible to improve the team?

3) Even if it's laughable, go with tenure.

If you absolutely have to make a tough choice, then tenure is the only way that everyone will feel good about it.  And, if played off the right way, they'll even find it sort of funny. A few months ago I was with my old, old, old buddy Keith. We've been hetero-man-love friends for about 8 years. It was his birthday party, and he celebrated with his high school buddies. One of the guys from high school nodded toward me, skeptical, and asked Keith, "Who's the new guy?" We all had a pretty good laugh.

Best Friends 9-12--the most "recent" ones--will understand that Best Friends 1-8, from early childhood, come first in the pecking order. Keith's not married or engaged, but if he chose his groomsmen, I'd expect him to choose those high school guys, and I'm completely fine with it.

One last thing...

Remember, your best friends are your best friends, and even if they'll be mildly insulted, they'll understand and they'll get over it. That's why they're good friends, right?

Good luck and let us know how it works out.

For more on picking groomsmen, find our other guidelines here.