As much as I would love to attend Grinnell, I should be clear that each of my kids chose a place which is absolutely wonderful for them, and I don’t have any regrets for them, only me!
In answer to the OP, we never regretted the college choices that our kids made. They were fortunate in one case to get into her first-choice school, RISD, and in the other case to get into school that was perfect matched for his talents and preferred location, UChicago. In the former case, advanced degrees ensued; while we have no regret about the choice (MBA at UMichigan), the costs were not something anyone had planned for. But eventually we worked things out.
Agnes Scott was the one that got away. I loved the architecture, surrounding town, and the sisterhood. Turns out she knew better. She is at a great college pursuing a major and minor not even available at AG. Plus the cost is lower!
Both of my kids were/are at the right school. Zero regrets.
I have several schools that I did not want my kids to consider. I didn’t bring them up, and they still have no idea they even exist. We did look at several schools that I would not have picked for myself OR for my kids, and thankfully they didn’t like them either.
One is at a school that I wouldn’t pick for myself, but she likes it.
Northwestern staff, faculty, & financial aid have been spectacular, but kiddo probably would have fit in better with the less-quirky students at Notre Dame, BC, or Dartmouth (which were my favorites).
U Chicago. I used to live in Chicago and would have loved her to attend there. DH wanted her to attend MIT. She decided on full tuition scholarship with Vandy. Yes, we are full pay. While she never looks back and really thrived at Vandy, there is very small part of me who believes that our frugal living style affects her decision. But she is doing CS with premed, the choice of school opens the possibilities for her.
Another UChicago regret. DD18’s older sibling goes to UChicago and I thought for sure that DD18 would fall in love with the school and the “life of the mind” during our visits to Chicago. Alas, DD18 didn’t want to walk in her brother’s shadow and decided to apply SCEA to Harvard and was accepted. I was happy for her when she got her H acceptance, but a piece of me was very sad when I realized that my dream of seeing both my kids together at one parents’ weekend would never be.
Rice. My H took our D on the tour and fell in love with it. Happy kids, great academics, well thought out campus, and housing situation helped to promote the full integration of diverse kids. (It really bothered us when we made some tours at other schools and saw kids self-segregating into groups of kids that looked like them). For me, I liked Rice because it is a direct flight for us and doesn’t have a liberal or conservative bent.
I thought at the time that my D should have picked Michigan over UDel. Partly because Mich is my alma mater, but mostly because i just got a vibe at UDel that didn’t seem right for her. Well, it totally wasn’t and she was miserable, but then she transferred to an LAC and was extremely happy, so maybe Michigan wouldn’t have been right for her either. No way to know.
S also chose another school over Michigan. That school (Columbia) was right for him, then wrong for him (bad personal experience led to him leaving after 3 1/2 years), then right enough when he finished another six years later. It worked out fine in the end but I think he would have been overall happier at Michigan.
Yes… While ours picked a great school with the athletic team that fits best, we wanted him to go to a similar school in size and academics a little further away from home and girlfriend. His school is residential and about an hour away, and he’ll be busy with athletics on top of academics, but still. It’s clearly where he wants to go and we are coming around.
My son made a level-headed decision that was a financial win. I wouldn’t change it for anything. I DID make comments throughout the process about where I would go in his shoes. But we are two very different people with different interests and abilities. He understood that.
Bloom where you’re planted. Both are happy and doing well. But I would have enjoyed Notre Dame football …
No regrets. She chose the perfect one, and she is totally happy there. It is the right fit for her in every sense. UChicago.
My D would say no way - she has loved every minute of her time at NYU. But I still harbor regrets that she didn’t have more of a “traditional” college experience. (A quad, sporting events, greek life etc). Also - NYU is so large, and there have definitely been times when I wished she was having a smaller, more personal experience. BUT - it was her college choice, not mine to make 
I would have loved my daughter to be at UVA. I just loved everything about that school from the history to the students to the libraries to the awesome town. She wanted University of Richmond (which I also liked a lot for her! great fit! smaller than UVA but great students). She will be attending Vanderbilt (which was her first college crush before we looked at other schools) because her FA pkg was the strongest of the three. I/She will always regret we had to follow the money instead of her heart. Oh and I always wish she had applied to either Princeton or Dartmouth; but she wasn’t interested in going that far north.
No. His college seems a perfect match for him.
To answer the question posted by the OP: No.
Just adding a different twist to the thread. My DD ended up exactly where I had always hoped and dreamed she would go; she just finished her sophomore year and tells me regularly that it’s the perfect place for her and she could not love it any more. I had a sense that she would thrive in the academic and social environment there and it’s gratifying to know that my hunch was correct. (So much of parenting is guesswork …) . It happens to be my alma mater and we both have enjoyed the mom/daughter bond, especially when she joined the sorority I was in and the same chapter advisor who initiated me was the one who initiated her (with the sorority pin she used to initiate me in the late 1980s).
I bent over backwards not to talk up the school because I wanted her to own the decision. The only “guiding” I did was to encourage her ** not ** to apply to a different and less selective school that was ED because of the likelihood she would get into it ED. In the end she decided to apply SCEA to my alma mater and ended up withdrawing her app to the 2nd choice school in late January.
I have had a (different) favorite school in mind for my DS, a rising senior, since this past fall. Again, it’s based on my sense of his personality and the school’s particular flavor. After 2 visits with him and a lot of research I think it would be a great place for him. It’ll be interesting to see if he ends up there. I’m keeping my fingers crossed. We still have several more schools he wants to see before making his final list.
We shall see what he (and, of course, the admission committee) decide.
I think my kids picked the right schools for them – although I do think D1 would have thrived at Willamette if she’d visited and applied there. It was on her list at one point, but off the beaten path for visiting, so it got dropped. I visited it recently, and could see how she definitely could have picked it.
I certainly see schools I wish I’d known about 40 years ago!
Michigan or anyplace other than a service academy/military, but he’s very happy where he is. My “wishes” are irrelevant.