My opinion, too!
I think it’s great you’re going to lunch. Just remember that all the “making friends, taking classes, getting involved” stuff can take time. She just moved in a few months ago so time has been involved in moving, rearranging her life and home, settling into a new married relationship. That is a LOT. She can and needs to move at her own pace. She may not be “happy” as you may define it but doing fine in her own timeline. She’s basically still getting her feet wet. Calling an old acquaintance/friend (who can come visit her) is a great sign.
Plus she’s dealing (or trying to not deal) with SIL who has been less than welcoming to any of it. And friend L hasn’t been supportive either. At least we haven’t heard of any real support. Constant doom and gloom and constant gossip with SIL (who hates Bob) wouldn’t make her a fan favorite in my book.
So I wouldn’t go into this as a fact finding mission. It’s not your job. Your “job” is to go have a pleasant afternoon eating lunch and chatting with MIL. And your “job” doesn’t require you to report back anything to anybody. Just have fun. Ask what you want as an interested party. And I’d truly refrain from gossip with SIL or Friend L (you can listen to what they say but NEVER add fuel to their fire.)
I moved my mom from NJ to NYC so it would be easier for me to take care of her. She reaches out to her friends in NJ and Queens to get together. Likewise your MIL is doing the same. It doesnt mean they are unhappy.
IMO, I would leave your MIL alone. She is now married, whether if anyone likes it. If she is happy, great, if she is not happy, she has to live with it. It’s not anyone’s problem to solve. At this point, it is better if everyone is supportive of the relationship because backing out would create more problems.
I’d avoid questions about particulars unless they seem like logical follow on questions. But I think it’s totally reasonable to say something along the lines of “gosh, you have made so many changes in your life in the last year - marriage, move, etc. It’s been such a whirlwind, but the dust is finally settling. How are you feeling about everything?”
If you are asking more direct questions make them more about her feelings, like “Do you miss the solitude or independence of living alone?” Or “How is it living in a community with so much going on?” (Fwiw, having all those activities and people around would be how DH would design hell.)
I think it’s okay at our age to ask older people about this, especially if you frame it as something that is helpful to you in thinking about your own future. As was mentioned, she likes to talk about herself, and honestly, most people like to be helpful, so she might open up. And people DO have different experiences with a community like that.
I also agree that she may not be enthusiastic about friends who have been critical because she may feel that anything negative will elicit an “I told you so!” Really, are there many life situations that play out 100% according to plan? Almost everything’s has something that comes as a surprise.
Your curiosity need not satisfy your SIL’s agenda, but it can still be informative and caring.
I think the question is what would you do with the information from your questions? What if she is lonely, unhappy about the relations, doesnt like where she is living. Would you be ready to fix it for her? IMO, if it’s not actionable information then I would leave it alone.
I don’t really agree with this. Often, just giving someone the space to say out loud the things that they have been feeling or thinking can be very helpful. Friends with serious health problems or ones who are ending decades of marriage welcome having someone listen and care. It’s an act of kindness.
With that said, I understand why, based on this thread, it sounded like a recon assignment!
There is never a requirement to do anything with information you receive in this situation. You put it in your back pocket and save it. Situations change daily so what’s said today in answer can be untrue tomorrow. Doesn’t mean you don’t ask the questions. An empathetic response is always helpful.
I also do think that SIL takes advantage of you to dig her dirt. You may have offered this date with MIL but SIL may have “led the camel
To water”.
I want to know where you’re going shopping! Is there somewhere she likes to go? My mom
HATES going shopping unless it was a food/grocery store.
People open up when they feel there is a safe place. MIL may just wanted to reach out to an old friend, but if it were turn into everyone is wondering why then she may not reach out again. If OP wants to be supportive, she could just try to spend more time with MIL and she would share what she is comfortable with, not with a lot of questions.
I don’t think MIL has much of an option now. She has sold her house, left her friends. The only option she has now is to move forward with the relationship. If the relationship were to go sour then the OP and her SIL would need to figure out where the MIL would move to.
Sorry. There are always options. Especially with a loving family around you.
I wouldn’t ask any digging questions that are outside the norms of your previous way of communicating. Any of the friends or daughter who want more information can make a date and come up and see your MIL. Call it a girls lunch which would exclude the new husband.
I agree with @oldfort. If she is unhappy what are you going to do with the information. MIL is an adult and has the right to make her own decisions. It doesn’t sound like she had a great relationship with her husband and maybe her needs and expectations are different than her friends or family.
I’d focus on having as pleasant a time as possible. If you get any info, fine and you can share or not as you prefer. If no info comes of it, at least MIL will know you (and your H) still care about her and are resources for her.
She’s had a LOT to process in a short time and I suspect she’s still processing.
She wants to go to J. Jill.
When she visited sil back in March they went there. It was on her things she wanted to do. Back then I told her we had one here in the area. Mil said she wasn’t sure how to get there. So, I specifically offered that because I know she likes it.
And, on the questions about what I would do if she says she’s miserable or unhappy or has regrets? I would tell dh, and then he and his sister could decide how to proceed.
I don’t expect that because, even if it were true, I think she’s far too prideful to admit she made a monumental mistake.
I would stick to questions like “my friend who I had lunch there told methe other day, when we ran into you, that she loved it there, what’s your favorite thing about it!”
I wouldn’t ask too many. She may question your motives.
I was hesitant to say something but the vibe I’m getting is that the sil and L are manipulating. Trying to get @Hoggirl to do reconnaissance. Hoping that mil is unhappy as they wish she has to be.
My opinion is not to get into anything that put you in any place but a place of friendship. For lack of another word. I suspect she’s not going to tell you anything because she doesn’t want it to get back to her daughter. And because she might be perfectly happy and content with her new life.
I am in my late 60’s, still working fulltime, a loving family and solid marriage…and some days all i want to do is to head to JJill!
I don’t think you want to get boxed in to the “mil whisperer” role. Your H doesn’t seem troubled by his mom’s state of mind, the fact that your SIL has opted for an awkward stance re Bob is not your burden to carry.
Take her to J Jill, find a cute place for coffee, drop her back home and tell her “gosh that was fun” and then let it be. You can leave the drama to everyone else. And if she chooses to confide in you that she is bored with sailing, she misses her bridge gang, she doesn’t like the way her new person does her hair, you can reassure her that anytime she wants to reconnect with her Pre-Bob folks she can make that happen.
I would also be very careful in repeating what she may say to SIL, or anyone else.
Be careful that you’re not being roped into being a flying monkey for Friend L and/or SIL. Don’t invite MIL out to lunch for the sole purpose of gathering intel/doing Reconnaissance for Friend L.
Some other thoughts to consider:
- sounds like Friend L might be a little hurt/angry that MIL calls Friend S and not her.
- MIL’s commentary to Friend S over the phone could have been something as simple as “It was great to reconnect. We should do it again sometime.”
- …meanwhile, Friend S and/or Friend L might be frustrated, disappointed, hurt, or whatever that MIL moved and hardly said a word to them about it.
- you should be prepared for MIL to have her guard up a little bit. She probably already knows that whatever she says to you, you will pass along to SIL. So be careful of not asking too many questions. You don’t want her to feel defensive.
- You also don’t want her to feel like the sole purpose of you inviting her to lunch and shopping is to gather intel for her kids.
- The questions you proposed are too specific (““Now that you’ve been at the CCRC for five months or so, is it living up to your expectations?” “Tell me about the new friends you are making”).
- Instead, keep the Q&A more general. Something like, “Hey, how’s it going living at the CCRC so far? ‘Friend I Had Lunch With’ said there’s activities & stuff she really enjoys here. What’s been some of your favorite things about it?” And how she answers that will tell you a lot…including what she doesn’t say.
- Just remember - If you don’t want to be the undercover MIL Intel Secret Service, you don’t have to sign up for those duties.

I realize I don’t know her but I might ask what is her most favorite thing and her least favorite thing about where she is living and then in your place I would share my most favorite thing and least favorite thing about something, like maybe your new house. Or I might ask what are the most surprising things about her new place or new lifestyle and share any recent surprises you have (not related to her). All in a very honestly friendly way and amidst other talk like do you have something in particular you are going to look for at JJill.