The woman is in her 80s! She’s wearing clothes she likes and feels comfortable in and likely are appropriate for her age and body type. In any case, Bob has not known her very long and in my view, commenting negatively about her clothing is not a good thing, unless she asked for his opinion on her outfit.
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That’s a cool dress.
Bob sounds like a butthead with no brain-to-mouth filter.
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I think he acts a lot like Sheldon from The Big Bang Theory.
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That was actually what I thought when i first read about his comment. And although we all think it was super rude, I think that from a guy in his 80s, he saw it as a compliment, given his own presumed social and generational background.
I think what’s telling is that she mentioned it to friend. She and Bob must have had many conversations during the cruise but the ones she repeats are the ones that stayed with her in some way - either she appreciated it (if he was complimenting) or she was bothered by it. I think the latter is more likely.
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When we go on any trip, we each get to pick one thing that is a must do for us. And we always did this with our kids too.
MIL really wanted to do that tea. She didn’t get to. I wonder how many things she did to please Bob…
Sorry, he just sounds self centered. If he cared about MIL, he would have made that tea happen…if not on the ship, someplace in London.
And clothing shaming is one step up from body shaming.
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I’m thinking about the clothing shaming thing. I would say that out of 100 times that DH and “go somewhere,” 94 of them he says nothing, 5 of them he compliments me, and 1 he tells me something doesn’t look good. Because it’s unusual, I take his criticism seriously. He’s not being mean or critical – just realistic.
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Does MIL have a birthday coming up? I’m going to start a CC Go Fund Me to raise $$$ for someone to take her to a proper and wonderful tea. (I realize it’s not the same as on the ship and I also am kidding - sort of - but someone take that woman out for a lovely tea!!!) 
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If this is the way Bob thinks is the way to behave when courting someone, I have to wonder how he’s going to be if he marries her.
I think we all agree that there are so many red flags 
that it’s very concerning.
It also seems that mil’s loved ones aren’t able to get through to her that this seems like a terrible idea.
BTW, the dress is lovely and mil looked great in it.
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Unless I missed something in the story we don’t know WHY she didn’t do the tea and if it was because of Bob or some other reason. I haven’t heard a story of Bob keeping MIL from doing anything she wanted to.
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I hear you, but if I went on a cruise my husband really wanted to go on, and the one thing I really wanted to do on that cruise was tea, and my husband didn’t attend said tea with me (and not whine about it), I would be very unhappy.
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But MIL doesn’t sound unhappy AFAIK. Sounds like she’s giving it until December at least before she decides to move in and marry the guy and the facility. The main red flag is that he’s been married a few times–but they (Bob and exes) all live in the same facility and nobody has shot anybody yet so… And maybe MIL likes being married more than being alone–same as Bob.
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The question is did Bob know it was the one thing she wanted to do? I could very well see her doing something like the following…
MIL: Oh look! They have tea!
Bob: Mutters his disapproval.
MIL not saying another word.
Just because she told her GFs that that’s the one thing she wanted to do, doesn’t mean she told Bob, or in a way that he understood.
Note - I still don’t like Bob and see plenty of red flags… I think it’s a bad idea to get married… Just trying to play devil’s advocate.
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Bob: Yes, they have it daily. Would you like to go?
MIL: I don’t really drink tea.
Deb922
This is my thinking. They are at the courting stage which is why any comments of what he thinks she should wear and saying her clothes are too baggy seem rude. You’d have to be super comfortable with a person to share such a critique. I certainly would not tell someone whom I knew just a few months that (if ever).
I also think the dress looks lovely for her age and figure. It is not truly baggy and more of an A-line flattering shape.
I hope if she does get involved with Bob, that she continues to dress to please herself, not him.
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Spilling the tea on the tea 
When mil came to our town to visit Bob and stay with him for the first time, we took them out to dinner. I asked Bob what he liked to do on the ship. “Walk the deck and look at the water.” Mil said then (at dinner in front of Bob) she really wanted to do tea one time. My reply was, “One time! I’d go every day!” At that dinner Bob claimed he was open to trying new things.
When I took her out to lunch after they got back I asked if they had gone to tea. She said they had not. When I asked why not, she simply said, “We just didn’t make it.” 
The travel agent had also said they should go to tea. Bob was aware of the tea appeal for mil.
I am only guessing, but I think that mil wanted to go, but Bob did not, so they didn’t. She either didn’t want to go by herself OR he whined about her wanting to go by herself and guilted her into not going. Pure speculation on my part.
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The dress looked lovely on your MIL.
I was married for 30 years. I don’t think I have ever opined on my ex’s clothing and vice versa. When it comes to my family and friends, I would only say something if they were trying to decide what to buy. I may say, “I think you look nice in short/long dress,” or “this color looks better on you.”
If Bob is critical so early in a relationship then he will just get worse.
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True. Everything we’ve said is speculation. This is a “Choose your own adventure” story at this point. But fun anyway. The betting line will be opening soon though.
Six months or less to marriage. Obviously already got plans of some sort. How early is it really?
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I was married for 30 years. I don’t think I have ever opined on my ex’s clothing and vice versa. When it comes to my family and friends, I would only say something if they were trying to decide what to buy. I may say, “I think you look nice in short/long dress,” or “this color looks better on you.”
If Bob is critical so early in a relationship then he will just get worse.
As you know, I already commented that for Bob to be critical of this woman’s clothing choices so early is rude, and I can’t think of what it would turn into if married.
The reason I am commenting again is that I was going to say something along the lines of what you wrote and then decided not to, but now that you did, I will to.
I was married for 36 years, I don’t recall my ex-husband ever criticizing my clothes. He might have complimented some of them, but I don’t recall his critiquing them. So, I would not take kindly to a new paramour of just a couple of months who critiqued my clothing choices, unless asked to opine.
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None of the men I was in relationships (including H whom I’ve been married to for nearly 40 years) has ever critiqued my clothes. Compliments, I’ve received a few. If I ask H sometimes he will give a preference of one outfit over another.
I’d end a relationship if I was getting criticism of my attire early in a relationship.
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