Your friends could be right, but you need to decide for yourself. There are three factors to weigh: how important that money is to you, how likely it is that he’ll repay it without a brouhaha, and how emotionally expensive that brouhaha would be.
There’s a cutoff, a point where having a couple hundred – or, if you’re a Kardashian, million – bucks back in your account is not worth continuing the pain. Only you can determine where that cutoff is, but if you decide to try for the money, you must create an additional limit: how long and hard you’re willing to push before throwing in the towel. By accepting that you’ve lost the financial battle and moving on, you’ll win the emotional war.
I’m assuming that you’ve tried to steer the conversation in other directions – jobs, books, pets, sports – and that these attempts are continually thwarted by the “We want details!” brigade. Do any of the other women in the group know your feelings? Can you talk to them about your discomfort level?
If no one else is motivated to help switch gears, you’ll have to maintain these friendships on a more individual basis. Single out pals for meals, where you’ll have more ability to keep the topics comfortable. And if people ask why you’re abstaining from larger get-togethers, you can give them another chance to give the sex talk a rest for a while.