Heck, I had an elderly aunt whose favorite activity was wandering down the aisles at TJ Maxx-- “you meet the most interesting people there”. It was walking distance from her apartment, she could treat herself to a hot pretzel from a little stand outside the store, the employees knew her by name.
So it’s tough to extrapolate from a text-- especially if the OP’s MIL considers just being around a crowd of upscale folks its own entertainment and watching the outfits go by!!!
Also there’s no emojis in that. On the other hand, maybe she never uses emojis when she texts.
She does use emojis when she texts.
Honestly, this trip was all Bob’s idea. He’s done it 20 times. I think she went because he wanted her to go. It’s what he likes to do.
I totally agree about different connotations in texting. I remember when I learned from a young person ending a sentence with a period in a text meant I was mad???
She posted a few pics on FB. I may have mentioned that already. Said on that post she learned quickly that the only things to take pics of were the water and each other - lol. Only one pic of the two of them together - the one I shared upthread.
The sense I’m getting is that she’s bored. But, I can’t tell if she’s bored with the experience or bored with Bob. Or both. No idea of what they are doing while on board. When I asked him what he liked to do on this trip, he said walk the deck and watch the water. But, he claimed he was open to anything mil wanted to do. Open to trying new things.
Tonight is the Roaring 20s gala themed night. She bought some Flapper accessories from Amazon. I hope she posts a pic of herself wearing them.
20 transatlantic crossings. That seems excessive to me.
The roaring 20’s night sounds like fun.
Re: Bob having been on 20 transatlantic cruises:
On the one hand, lots of people have different travel preferences. Some people do the same beach vacation every year for 20 years. Others go to a favorite cabin in the woods or “the lake.” And some people like cruising.
On the other hand, I suspect that for the cruise loving crowd, most of them enjoy going on cruises to different locations, not going on the same exact cruise every time. So Bob having been on this very same sail 20 times is…different. 
My gut says that Bob is a bit persnickety about having things his way. So whichever lady friend he’s with likely has to be willing to go with the flow and let him get what he wants with no fuss. In other words, a little self absorbed.
I am wondering if Bob likes to be the one who is experienced - the teacher, the guide. It makes him knowledgeable and gives him a certain kind of upper hand, power, control. It creates a certain dynamic.
This isn’t to say he doesn’t genuinely enjoy this trip (or that MIL can’t enjoy it too), but it does make for a different vacation than them both exploring Cairo, for example, together for the first time.
There are certainly times it can be good to be with someone who knows the ropes. It can also be very annoying if you have any ideas of your own. Who knows? He may be trying to recreate some prior perfect crossing --without even realizing it.
As always, loving every installment of this saga.
On a transatlantic cruise, it is mostly, or all, sea days. Some people really like those as they don’t have to deal with the ports and people trying to sell them stuff, get to gamble in the casinos all day and all night, have food available all the time, have on ship activities included in the price of the cruise.
I know people who go on cruises with ports and still never get off the ship. They like doing the ship stuff, especially when then ship is empty.
I think Bob likes to know what his day will be like, and that he can be in charge all the time. He knows the waiters, the bartenders, the way to the theater. He knows which food is best on which night. He knows the best time to get a haircut or even when to play mini-golf. He’s the big deal. And very impressed with himself. He may even know a lot of the other cruisers on the trips.
I also speculate that as he ages, this is familiar to Bob and that provides comfort and perhaps masks shortcomings.
People go to Disney multiple times They go to the parks, the cruise line, the timeshare resorts. It’s a whole industry.
Some people go to the same resort every year. Go to the same tropical island year after year. It’s all about what you like to do.
Same thing as doing the same cruise.
Having serves on a US Navy Destroyer, a North Atlantic cruise, no matter how big the ship, is not my idea of fun.
If he likes to walk the deck and look at the water then a transatlantic cruise is the way to go! I read the great experience comment as Bob’s done this 20 times and if she hasn’t he may have sold her on it as something everyone needs to experience. If she is a bit bored she may be reminding herself of that.
My octogenarian in-laws really enjoy the sea days on a ship, being able to totally relax and not be on a schedule.
If Bob is loyal to one cruise line he’s likely to have lots of extra perks too.
Hope your MIL isn’t too bored!
And no single supplement if they are sharing a stateroom!
We are some of those “people go to Disney multiple times” people! However…
I’d be bored out of my mind going on the very same cruise 20 times in a row.
I’m sure the 20 cruises have been over 10 or more years. Just like things at Disney change, things on the cruises change too. Different food, different theme parties, different shows and entertainment.
I went on a Disney cruise through the Panama Canal that was 14 days. Some people we were originally assigned to sit with for dinner (they moved to be with their favorite waiter, so they’d been on enough cruises to have a favorite waiter) were doing this 14 day cruise, then a 3-5 day one, then a 7 day one, all on same ship, from Miami to Alaska. BTW, no children in their group on a Disney cruise.
They knew all the games and quizzes and had seen all the shows a number of times.
The only thing “wrong” about doing the same vacation over and over is that you aren’t getting to do something new (if your vacation time and/or budget are limited in any way, which they usually are!) Anyone who owns a vacation home is probably familiar with that challenge. But they also know that it’s never 100% the same every time. And they know they love the place/trip.
Personally, I can’t imagine doing a crossing 20 times, but I also suspect there are people who would be miserable with my “perfect” day on repeat for most of the summer.
She posted some more pics on Facebook. None in the Roaring 20s gear, but I was happy to see some regardless. I gotta say she looks pretty smitten/happy in one of them.
Here was her accompanying caption:
We spend a lot of time eating and walking. We’ve seen some great entertainment and attended very interesting lectures. Our time has changed 4 times, and I’m sure we have another coming up in UK. It has been a great trip with basically calm weather, though it was pretty windy this morning and foggy this afternoon as you can see by wind blown hair.
Sil had said mil previously said she didn’t really want to go to lectures?? And, she did use the word, “interesting,” to describe them 
. She told me she hoped to go to tea at least one time. I hope Bob was amenable to what she wanted to do as well.
Well, if she never gets to do any of the things she wants to do, she will have to decide if that’s the way she wants to have life going forward or not. She is an adult and has agency. Here’s hoping that she is able to get things she desires.
I think her original text message to you that it was a great experience was her commentary about the cruise itself. I infer you were likely more interested in her commentary about her time with Bob, but she was truly speaking of the cruise experience, not Bob so much. Hopefully when she returns, you’ll get more thoughts about the time with Bob aspect.
PS, I’m happy for her at her age as a widow that she is getting to go on a vacation and have a new experience (the cruise) whether or not it works out with Bob!
Sometimes a new friend/partner can inspire you to try something different.
My good friend has picked up skiing and sailing because of 2 different partners. That being said, she gets bad seasick when she is on a boat and she has sailed to Australia.