First, if you don’t already own multiple Fat Tire Bikes (you will eventually), find one to borrow (see if the LBS has a demo). Next, be sure the novice gets the better bike. This will allow them to ride easier with you. Also be sure that their clothing is appropriate for the weather. We assume that people know what layers to bring but that is just not the case. Feet and hands are the most critical. It’s relatively easy to layer up or down while riding but if the hands or feet get too hot or cold it’s much harder to get them back under control and regulated. Winter would seem to be the most difficult weather to manage but summer brings humidity and insects that can really kill a fun ride. So, consider all environmental factors before inviting someone for the first time. Finally, put the bikes on a rack outside of the vehicle. Your date may appreciate some space inside the car to change and layer up or down before and after the ride.
As in real estate, location is the key. Do not attempt the most difficult terrain or trail in the area for a first ride. Instead, pick out a nice dirt road route and if possible a parking spot where your date can get situated on the bike without feeling conspicuously inexperienced. After a couple successful Fat Tire Bike dates, you can bring them to the local trail. Stack the odds in your favor. Avoid ice, mud and rain at all costs.
Fat Tire Bikes seem to accommodate riders of different sizes fairly easily with simple seat height adjustments. Remember, this is a first ride, an initiation into the Fat Tire Nation culture, so be nice for the entire ride, especially if you want to make good use of the private parking spot you secured earlier. Some riders have told me stories about how they still managed to get their workout in by hitting every hill hard and doubling back while their date slogged along… that’s not nice. They didn’t get any points for the workout or the parking spot. Just enjoy the date. Talk to your companion to help distract them from being tired. Help make the time fly. Dates that end with the couple trying to think of where the time went are the best. Then show them the GPS data (don’t show them that you never got your heartrate above 115 but let them see the map and the elevation gain) There’s a few phone based options that allow you to do this at the parking spot… don’t kill the moment by speeding home to upload from your Garmin, they need immediate gratification.
While riding be careful not to put your date in a position where they need to answer to many questions with long answers. Don’t ask them about their job or politics. Ask several questions where they can answer with “yes or no”, some fascial expressions and hand signals. If riding for more than one hour and weather permitting, bring a back pack with a little snack (bagel, muffin or a couple of beers works well). Be positive, tell them how good they look on the bike, even if the fit isn’t optimal. Tell them how much you enjoy riding with them and riding in general but don’t paint yourself into a corner where you can no longer ride with your normal group. Keep the date (present and future) special. As soon as they invade the regular group or prevent you from enjoying your regular group, it’s over.
Only you can judge how far or fast to ride on the first date. It’s a big responsibility and you need to have some contingency plans in case the ride goes poorly. Design a route with some bail out roads. Return to the parking spot with energy left to burn, the day (or evening) could still be young. Always leave them feeling like they had some more to give and you may get some more in return.