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Gear Prudence: My boyfriend and I are breaking up. It’s mutual and there aren’t that many hurt feelings. However, for the past year, we’ve been doing a monthly group ride with the same group of friends, and now that we’re not a couple, I’m not really sure what happens. Both of us love to ride, and we have both become close to these people. I don’t want to stop going (because they’re my friends), but I also don’t want it to be awkward if we both go. Help! —Since Partner Left, I’m Torn

Dear SPLIT: Custody arrangements can definitely be messy, especially when the thing you’re trying to sort out is a mutually enjoyed activity with some mutual friends. Alternating with him on a monthly basis would seem to be solomonic, but it’s also a solution that cuts your riding-with-friends time in half. That’s not really fair to you. GP thinks that you should keep going. Just show up and ride with your friends. If he comes, that’s fine, and if things are as mutual as you suggested, then awkwardness need not prevail. Barring this, there is another way: Ask your friends to start riding every two weeks! It’s twice as many miles for them, but you’ll be so rich in group rides, you and your ex will have no trouble splitting them. —GP

Gear Prudence: My best friend and I like to ride together. The only problem is that he wants to do the same exact route every single time. Even worse, it’s the Mount Vernon Trail, which, this time of year, is so annoying since it’s crowded with other bicyclists, runners, walkers, and kids. I’ve asked him to try something new, but he flat out refuses. He says the trail is his favorite and he doesn’t really feel the need to bike anywhere else. What should I do?—Stubborn Acquaintance Mitigates Enjoyment

Dear SAME: Before GP addresses this so-called friendship, it’s important to validate your feelings about the Mount Vernon Trail—it is really crowded! And those crowds do turn off a lot of cyclists, who seek other places to ride this time of year. If it’s a stressful time for you, GP understands your reticence to suck it up in the name of friendship.

That said, what kind of friend is this? Your buddy sounds like a total stick in the spokes. Sure it’s his favorite place to ride, but to be so uncompromising is totally unbecoming. One way to deal is to just bail on this guy, but if you want to keep riding with him, probe a little deeper about why he likes the route so much. Maybe if you can identify an analogous experience and show him that new doesn’t have to be that different, he’d be more willing to try. —GP

Gear Prudence is Brian McEntee, who tweets at @sharrowsDC. Got a questions about bicycling? Email gearprudence@washcp.com.