Kathleen, congrats on taking these first steps in pursuing what will definitely turn out to be a great adventure.
But first, your quote: "I'm often sitting next to him on the couch as he reads and posts for hours on end...like I'm not even there! "
Ugh, i've been very guilty of that myself a few times, so it made me laugh a bit as it struck a chord.
I took my girlfriend out backpacking for the first time in her life when she was 26. Like you, she fears/despises certain aspects of camping. The bathroom thing has been an issue. What has helped tremendously is this following product.
She feels that it makes things easier, cleaner, and faster
In terms of tents...yeah she will never do a floorless shelter either. We use a tarptent Double Rainbow, with zero complaints. It's as traditional of a tent as you're going to get, but with UL fabrics, and a respectable weight. It's clearly not the only option out there, but it happens to be a tent that we have, and works well. It's also extremely livable, which 2 doors and 2 vestibules. A nice "his" and "hers" and no need to crawl over each other in the middle of night to take a leak. We went from a 5lb sierra designs traditional tent to the Double Rainbow and my girlfriend wasn't even phased...they were the same in her book. 2.5 lbs, or split up the poles from the body, and it's even lighter per person now. We've tried to go with a lighter tent in the past (cuben duomid with duo inner nettent) but it just wasn't as livable for 2 adults...it was worth the bump in weight to live comfortably.
Our first trek together was to 13 Falls in the Pemi Wilderness area of NH. A very easy, gradual hike, with an opportunity to camp outdoors in a somewhat secluded site. There was also an outhouse which made things easier for first timers. You could simply do a there and back to get a feel for the outdoors...no need to summit any peaks.
If you're feeling ambitious, you can always do mt liberty in NH. This one is steeper and a bit more aggressive, but it also offers a nice tent site (liberty tent site) and an outhouse. If you make it to the tent site, you can easily tag the summit, which is only .6 miles away.
You're gonna have a lot of fun! You might love the outdoors. After only a year of outings, my girlfriend will be joining me on the John Muir Trail this September...but who knows what 21 days will do to us :D
I haven't had a chance to read all the posts, so please forgive me if I've missed some details. But I would highly recommend just testing the waters first with some day hikes. Maybe even some aggressive steep day hikes just to get an idea of some of the hardships. The worst would be to not enjoy the activity, and then be forced to spend a night out there on top of it all. Also, do you enjoy photography? A camera can add a different level of appreciation to the outdoors. I enjoy sleeping outdoors, the gear (of course) and the views, and those would be my main motivations for going outside. Whereas my girlfriend truly enjoys photography, which provides her with her very own form of incentive to get out there. It's great that you're doing this for your boyfriend, but I think it's valuable to find something that you can take away for yourself at the end of the day. Have fun!
Another thing that I find helpful in making the trip enjoyable for the both of us is splitting the responsibility. The first couple of trips, my GF admitted that she felt like she was tagging along on "my" trip, which kind of bothered her. She would watch me boil the water, set up the tent, hang the bear bag, etc etc. These things are not rocket science by all means, and can easily be learned and taught. I would encourage you guys to share your knowledge of equipment and tasks with one another, which would make these tasks more engaging and efficient .
Cheers! (and wait for perfect weather)