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Gear Prudence: Every time I lock up my bike, I feel awkward. I often drop the lock, fumble around with it, and take extra time with the key.  It reminds me, to be honest, of some of my present day experiences on the dating scene.  Each time that I lock up at a new rack it’s a different experience.  What can I do to be more confident in this area? —Lacking Overt Confidence, Klutzy

Dear LOCK: We’ve all been there. You hop off the bike and find a rack. But maybe there’s another bike there or you come at the rack from the wrong angle, and as you can’t quite find the keyhole and connect the mechanism, you feel the eyes of gathered onlookers burn into the back of your head. Your mortification and embarrassment inversely correlates to your manual dexterity and only eventually, after the beads of sweat coalesce on your brow, do you achieve the simple task of affixing your bike to a stationary object. It’s rough.

The dating analogy is apt, but your takeaway is wrong. Each rack is a new and different experience, so learn from your previous ones rather than repeat your past mistakes. Befuddled by parking meters? Avoid them. Have a good time with a street sign? Try that again. But more that than, real confidence can only come from self-assurance in the proper functioning of your own equipment. Know how it works, where you can wedge it, its length and reach, and how much jostling it can handle, and you’ll have mastery in nearly any situation. —GP

Gear Prudence: I live near H Street and its forever forthcoming streetcar. I’ve heard lots of stories about bicyclists wiping out from riding over the streetcar tracks, but everyday I see more and more people on bikes still riding on H, despite the obvious dangers of the tracks. Why do they keep doing it? —Trolley Route Amplifies Crashes, Kindly Skip

Dear TRACKS: The streetcar tracks have been the undoing of many a cyclist. They eat bike tires just like hipsters eat [insert name of popular dish at any Atlas District eatery]. If you ever ride over the tracks, you need to be especially mindful to position your tires to cross in a perpendicular manner.

There are close parallel bike routes to H Street; both G and I streets NE from 2nd to 14th have sharrows and contraflow bike lanes. That’s pretty convenient, though contraflow bike lanes aren’t without their own hazards.

But as to your larger question: Why are people bicycling on H Street? Because that’s where the stuff is. People expect to be able to bicycle from door to door, and they’re willing to abide certain risks to do it. —GP

Gear Prudence is Brian McEntee, who blogs at talesfromthesharrows.blogspot.com and tweets at @sharrowsdc. Got a question about bicycling? Email gearprudence@washingtoncitypaper.com.