Meetup.com or ask another female that's out in the water. If she is the shy type, there is always Google

La' Oloa Bay and Kua Bay- usually.
If by chance the waves are up and you feel out of place, paddle in and ask a surf shop where you should go. Buy a t shirt at the shop in exchange for intel.

Cowells beach in Santa Cruz (aka "can-of-screws") should meet the requirements for "culture", safety, cheap lodging availability and gentle waves.
If he prefers the group thing have him check out...

http://www.grindtv.com/outdoor/blog/50913/kids+embarrassing+tumble+on+ski+slopes+going+viral/

Ski patrol on my home mountain and your's

This has worked well for me in the past:
https://www.sportube.com/Ski-s/1814.htm

http://www.laketahoenews.net/2009/09/warning-from-dog-owner-rattlesnakes-near-caples-lake/

Where have you seen those bastards at 7800 feet? I know about the one near lake Margaret. Any other hotspots that I should keep the pup away from- or at least on leash?

"Vail at Kirkwood". Sounds like an oxymoron. We're going to become civilized now.
Although, all kidding aside, this was the best of the three options for Kirkwood.

Of course, in time, we will...

We are leasing/renting our Kirkwood studio condo in The Meadows, which is walking distance to chair 6. If interested, PM me for further details. Absolutely no smoking and please, no pets.
...

He's living in SLT and working weekends right? If the OP has the means, I would go with a mid-week pass for both the heave and the wood. He could probably get a mid-week pass at both resorts for...

Just to be clear, the studio would be booked by one couple at a time. Think of it as a ski lease but without having to share the space.

To the above posters that are looking for a ski lease:
I have a studio in the kirkwood valley that's walking distance to chair 6.Amenities include, underground parking, hot tub, cable tv, ski...

On a positive note, they can always kill the day at the Rancheria playing pai gow poker.