Me personally, I would do my level best to seek out a family washroom so that we could answer the call of nature without the worries of who must use the facilities unattended. But I know that's not always possible, for whatever reason. I have taken my DS into the ladies washroom with me many times when he was smaller, if DH was not with us. That said, I let him be the lead on when it was time to transition going into the men's washroom alone. By the time you start having the conversations that start out with "but Mom, I don't want to go into the girls washroom....I'm a BOY!" or "I can go into the men's washroom by myself, Mom!" then its time to send them into the guys side alone (with the proper reminders about what to do if he feels uncomfortable, unsafe, etc.). I think this readiness will vary widely depending on the independence level of the little fellow in question. I do feel for you, OP. Its a tough transition to make and your comfort level will be sorely challenged. The maternal instinct is to protect, and letting them make this next step in growing up is hard. Have lots of conversations ..... LOTS ..... about what your young man should do if he runs into difficulty while in the washroom alone. And if it were me, for the first little while, I would have him stand outside the washroom door while the ladies tend to business, then switch up afterward (having you stand outside the men's room while he does his business). That way, you can call to him if he seems to be taking an unusually long time, or he can call to you (and have you able to answer and assist) if need be. The double standard between raising boys and raising girls does sadden me a bit, though. Moms of little girls who never have to face the mom-and-son washroom dilemma will never understand the conflicting emotions associated with this situation. Yes, I understand how girls need their privacy protected in the washroom (I am female myself.....so I "get" that completely). And its wonderful that moms can accompany those young ladies into the washroom indefinitely with no fear of retribution. Yet.....the mothers of sons also need the comfort of mothering and protecting their kids, but its much, much harder to find that balance (this thread is a perfect example why). We're supposed to tell those little boys (and yes, at 7 and 8 they are still "little") to man up and do their thing at 5, 6 and 7. But if the tables were reversed and the 5, 6, 7, 8 year old girls were told to use the washroom on their own, without Mom or another responsibly (and safe) individual to accompany them, the alarm bells would be sounded and there would be a public outcry. The little guys are just as vulnerable, but yet the expectations (and the way the situation is viewed) are totally different than for the young ladies. I had this conversation with a friend of mine who has three daughters, no sons. I asked her how she would feel if her 7 year old was made use the washroom completely alone at Disney World, each and every time. The answer was "no way in he**". And I understand completely. Because that little girl is still a little girl, and needs the safety and comfort of having her mom nearby. Many little boys (and their moms) need that, too.