Training with people of different abilities

One of the things that I lack in my training is the ability to work with other people.  It is something that has plagued me ever since high school and I wish it could be different.  I love to go for long runs or long bike rides by myself and see how hard I can push myself and not have to worry about other people, but there are those times where it's nice to be able to work out with someone else as well.  Unfortunately, I don't really have that.

In high school, I was on the track team and we had a really good relay team.  Every year we went to Nationals, and my senior year we even competed and medaled at the Millrose Games in Madison Square Garden.  You would think that our workouts were always done together, right?  Nope.  Remember, we were in high school so we wanted to be "cool"  So working out with the relay team was difficult at times.  Not because of obvious reasons, but because no one wanted to get smoked by one another.  There was always the fastest person and the slowest person in the relay.  I was neither so I'm good with that.  So during workouts, we all had to stick together.  This wasn't exactly fair to the fastest person in our relay, nor the slowest.  What happened was we all had to finish around the same time.  Which meant the fastest person of our relay had to slow down a little to stay with the group while the slowest person had to work harder than anyone to keep up.  It was great camaraderie, but looking back, I think we held our fastest person back a little bit because if he ever got ahead of us too far, we yelled at him to reel him back to us so we wouldn't look so bad. 

So why do I bring this up now?  High school was years ago and has no relevance, right? 

I've mentioned my racing/training buddy Leo a few times and one thing that upsets me is that we never really get a chance to truly train together.  Yes, there are times we head to the pool together and we're in the same area doing our workouts, but it's not like we go out and do a 10 mile run together or a 2 hour bike ride together.  We're just 2 different athletic abilities and speeds.  And by no means is this a knock against him or a post about him in any way shape or form.  This is about how I think we would both really enjoy to be able to work out together.

I am somewhere of a 6:10-6:40 mile runner depending on the course and what workout I'm doing, and Leo is somewhere between 8:15-8:45 mile.  Both are really good and we are both happy with where we are.  Same thing for our bike speeds.  I average about 21-22 mph depending on the course, and Leo averages about 17-18 mph.  So training together is really difficult.  I either have to slow down considerably during a workout which wouldn't benefit me in any way, or he would have to speed up significantly and he wouldn't be able to keep that pace up for an extended time.  So we would end up killing each other and getting mad at the other person.  I would be mad that I can't workout hard and would constantly be pushing him to speed up which would get him mad at me, and he would also be mad that I would want to push the pace too hard.

So how do we solve this?  There are some times we do workouts together that allow us to do the same workouts and we enjoy it.  We do my hill workout together during marathon training which allows us to work out together and we also do some of the speed workouts with our running team so that keeps us training together but the majority of our workouts are done separately.

Even this weekend coming up is causing problems.  We want to go biking on the same route for a few hours which would be a nice workout, but due to our different speeds, we would fight constantly.  And one thing to know is that Leo and I fight about anything and everything.  I fight and bicker with him more than I do with the wife.  And that's what makes our friendship so great.  We can fight and bicker and then 5 minutes later we are back to normal.  So if we have a 2 hour bike ride planned, do we just go at our own speeds and at the 60 minute mark, just turn around and we'll meet up around the end of the route?  Do we ride together for a certain amount of time then separate?  Either way, it's not like we're working out together even though we would start and end in the same spot.

Our training schedule is also very different.  I like to do my long bike rides and long runs on the weekends since that's where the most time is.  Leo wanted to do an hour bike ride and 60 minute brick workout this weekend when we were going to do a 2 hour ride.  Difference of opinions and schedules and neither is right or wrong, but it's just hard to coordinate schedules. 

So one of the things that I miss the most is having the ability to have a workout partner at times.  I would love nothing more than to be able to jump on a bike or go out for a run and Leo and I be able to talk, joke, catch up on things in our lives, push each other, and enjoy the workout together.  I wish I had that in my workout arsenal.  It would break up the always trying to push and push and beat a previous time.  Some of my workouts would be more fun.  I'm sure Leo feels the same way. 

So what is the best way for people who want to train together but are 2 different speeds actually train together?  It's something that I want to know so I can do it.