It wo0uld seem that even something innocent as sharing a milkshake would be chaotic.
They can’t move The Bubble around fast enough; yet they can’t run security checks to clear all possible suitors. How does it work in real life.
Anecdotally from 40 years ago, one of Ford’s sons mentioned that his secret service detail really hated when he was out on a date and he made it through a yellow light just in time for the detail following in the car behind him to get stuck at the red light. His advice to Amy Carter was “never do that.” Granted, she was eight at the time, so this wasn’t too helpful. His other advice was to get in good with the kitchen staff or you’ll never get snacks outside of mealtimes; that was probably more helpful to her.
Those young men better remember that the 82nd Airborne works for her father. Oh, and the old “running out of gas” ploy isn’t going to work. The “yawn and stretch” ploy would still probably work if you don’t mind hearing everyone in the Secret Service detail snickering.
This article from November 2015 says:
They have friends and go to their friends’ houses and have sleepovers, but I would guess that they know they will only have to be the President’s kids for a short while longer now, they can hold off on dating. It’s not like they are going to miss anything.
He did mention when he announced his second campaign that he wouldn’t mind at all having the Secret Service around when he had two teenage daughters…
What do you mean *not missing anything? *. I believe many high school students really like dating.
He’ll still have them around. Secret Service protection is for life.
Yes, but now he has ALL of them.
But his kids won’t. Malia’s protection goes away as soon as he leaves office, Sasha keeps it for only a few months.
Gives a whole meaning to the old trope about fearing your date’s father when he can, uh, launch a drone strike on you if he wants.
Meaning it’s not like their father is beginning an eight-year stint in the White House just as they hit their dating years. They are only now in prime dating range, and he’ll be out of office in a few months.
Unlike, say, a kid whose parent is elected when s/he is 14. Eight years later–22.
“Prime dating age?” Are they spinsters once they hit their 20’s? 
To a teenager wanting to go on a date, a month can seem like an eternity.
I don’t know the GQ answer, but it reminded me of this funny meme from a few years ago:
Chelsea Clinton was almost 21 when Bill Clinton’s term was up in January 2001. Did she have dates when she lived in the White House? She was at Stanford for the last couple years. Did the USSS follow her around when she wanted to go to the movies with a guy?
“Two students, six adults, please.”
Weren’t the Bush twins always sneaking into Washington bars while underage?
If you are a scion of the British Royal Family, it is for life. But they seem to manage OK.
I read something about this when doing some research on the Secret Service, but it was a long time ago so no cite. The gist of it was that they’re not nannies, but they do prevent their underage charges from coming to harm. So with the Bush girls, it wasn’t their job to stop them from breaking the law by drinking or using fake IDs, but it was their job to intervene if the girls got falling-down drunk or tried to drive. So if Malia or Sasha slipped away for alone time with a boy, I imagine the detail would wait outside patiently. I think it’s also part of the job that they’re not supposed to tattle to the parents, because they want the kids to trust the officers in the detail.
They turned 21 in November 2002, so they didn’t have that long to wait.