Dilemma re: 2e 15 y.o. who still needs a “babysitter”

When I had a similar need for a different reason, I hired a young man who lived in the neighborhood to hang out / mentor my son. An overnight was required. If I remember correctly, the young man was around 19-20 at the time. I knew his parents, and he seemed to have some similarities to my son. I appreciated that his parents knew the situation and could step up in case of emergency. It worked out well ... no emergencies.

I think the job title for this position would be more like "freelance emotional support person" rather than "babysitter." :)  My daughter also has anxiety and had similar difficulties being in the house alone in her early teens which she has been able to move on from. Kudos to you for being so thoughtful about supporting your son while also taking care of your needs. A few thoughts:

1. I would encourage you to consider asking your son to identify what he might like to do/where he might like to go when you have other plans. There may be a structured group activity somewhere that dovetails with the time you would like to be out of the house. He may be able to identify a friend where you could start with inviting that person over for a hangout, which could create a more natural opening to ask for a reciprocal hangout later. We often don't really know what kind of support others need unless we ask, and trading quiet evenings at home (for any reason) might be higher value to another family than anticipated.
2. Consider whether borrowing a dog from a friend or neighbor or on a shelter foster day would be helpful. When my daughter was having a lot of anxiety in the house, it helped her to be with our cat at the time who was quite a scaredy cat. My daughter knew that if she heard a noise, but the cat did not respond in a concerned way, then that meant she didn't have to worry about the noise either. It's possible that the companionship of an animal who is also listening and aware of the environment could help your son as well. (It is of course harder to borrow a cat since they are so territorial that they don't tend to act normally in a different setting.) 

3. My daughter who is 18 now babysits and volunteers and said she would be happy to occasionally work as companion to a fellow teen working through anxiety. She can cook simple meals like pasta or scrambled eggs (and is particularly skilled at pancakes, but I digress.)  She is going off to college in the fall but not very far away so will continue to be home some weekends for school year availability. Feel free to reach out and we can chat if that may be of interest to you. You could also look into creating a job posting for a Cal student. 

   Best wishes on finding solutions that work for your family,

   Catherine 

What about hiring a college student (guy) to come and 'hang out' with him, paid of course. He'd probably enjoy it more than a grandma type, and you if could make it a regular gig it would be worth someone's time!

Consider that you maybe could ask another parent to have him over. I definitely get not feeling instinctively comfortable with the ask but if you're in contact with a friend's parents it doesn't have to be a whole thing about his anxiety, or a barter negotiation, just a simple ask. "hey, we're both going to be out really late and we were wondering if you'd be game to have our kid over for dinner?" 

Do you have a neighbor who might be game to have him help babysit if it is free? You can tell the parents that you are trying to find him some light companionship while you're out and tell him that ...whatever. The neighbor's 5th grader needs homework help or the neighbors have a new baby and need someone to play Uno with their eldest.  When we had a toddler our neighbor regularly sent her pre-teen over to help us (and it was a huge help) by playing doll house but we understood that we were also babysitting a little bit. 

Or look for a college kid and spell it out. Again, I don't think the anxiety needs to be spelled out in full, just "we're looking for someone who has some experience babysitting to come make dinner with our teen" or frame it as light tutoring. A drawing coach. 

I would just let go of the screen time thing, though. Choose your battles. 

As a parent of two teens with anxiety, I like all these suggestions so far and depending on your specific child, any of them are worth trying. I'll amplify the suggestion of finding him his own activity to do during a time when you'd like to go out. For instance, Games of Berkeley has evening events many nights of the week and I believe 15 year olds can attend without a parent. Of course that only makes sense if you're going out to dinner for a couple of hours, not a late night concert, which is the specific activity you mention you'd like to do. For that, I would suggest saying to your child, Hey dad and I like this artist who's coming to town on x date, we're going to buy tickets for all three of us to go to the concert! And you all go. If child has a good time, great! If child does not enjoy your adult musical taste, the next time a concert opportunity rolls around, they might find themselves more mentally prepared to stay home alone - a little scary perhaps, but better than being bored to death for four hours. :)