I just remembered! Stars Earn Stripes. I've seen the pilot and now I'm watching the second episode. It's celebrities (they aren't wimpy ones though, they are trainers, action stars, boxers...) and they are paired up with military members. Green Beret, Seals, Snipers....
Anyways, they go on mission to earn stripes, and their stripes equal money for the charities that they picked, and I'm pretty sure all of the charities involve military stuff. Like Veterans, or families.