As far as I am concerned, there is no absolute right/wrong way. What ever works best for you is how you should handle it. In my case, I balance the bike and put the jiffy stand up. When I'm ready for her to get on, I stand up and support the bike's balance with my hands and my legs. I'm a big guy so this works for us. Someone shorter may not be able to work it that way.

 

When I rode two up, I had an 08 Ultra Classic, I always got on, stood the bike up, but left the kickstand down. Let her mount by stepping on the left passenger floorboard. with her left hand on my left shoulder and her right hand on the Tourpak backrest, she would swing her right leg between the rider backrest and tourpak. After she was seated and ready to go, I would put the kickstand up, Start the engine, let her warm a bit and go. worked for us until she got her own bike. You getting on first and standing the bike up is easier than her getting on and then you have to stand it up with her weight too.

 

She should just get on the back of someelse's bike and make you case her. LOL

 

I used to get on and put up the stand then tell her to climb up but every once in a while she will be too slow getting herself to center and I don't like the almost-gonna-tip-over feeling when that happens, so now I still hold it straight up but I leave the stand down so in case I lose it there is a pretty good chance the stand will save me. After she is settled its kickstand up till she signals for a bathroom stop.

Lately I am just so glad when my wife comes along that I don't even let myself get mad when she clips the top of the bags with her boot.

 

I get on then my wife. I watched a buddy’s wife get on when the bike was on a slope and the bike went over the other way.

 

OK, I get on mine first and then she does not get on until I am ready for her. She will ask me if I am ready and I will then tell her. Now for some they leave the jiffey stand down just in case they get on without saying anything and catches you off gaurd pulling the bike down or you trying to catch it, at least this way it will just stop at the stand. So far I have had no problems with her getting on or off as long as she asks if I am ready..................

 

Just upgraded from a Fatboy to a Road King. GF had no trouble swinging her leg over the Fatboy.
I always get on the bike first to stabilize it. She tried stepping on the footrest and climbing over....I'm 6'3" and 250 and this method still required me to brace the bike.
Now she lifts the footrests up, and just swings her leg over. Don't even feel her getting on.
I would shy away from letting her get on before you. You won't have any control over the bike.

 

I'm always the first one on and the last to get off, and there is always a verbal "are you ready" before getting off or on.

Wife gets on the left side with me already on, the bike upright but the stand down just in case, same when getting off, stand out first.

 

I found it easier to put the bike on the center stand and let the wife get on first, then I get on - start it - put it in gear and pull off. The stand retracts itself.

 

There is no right or wrong way. Whatever works best for you. The key is communication. I get on first, raise the jiffy stand, steady the bike, then wife puts her hand on my shoulder after she asks if I am ready and I reply yes. She then steps on the passenger floor board and gets on and situated before I sit down. Same thing with getting off. I steady the bike, wife puts her had and my shoulder and asks if I am ready and after I reply yes, she stands up and gets off. It has worked for years. I tried getting off first and then her and I just didnt like all that moving around on the jiffy stand. We only tried that once and then went back to what we felt more comfortable with.