I have a dear friend that is ALWAYS late. I have been able to maintain a good friendship with her for about 6 years. I learned early on, NOT to depend on her for anything important and just arrange dates and tell her to show at at the place designated without it impacting get togethers. I don’t get rides from her as she would be late and so far is has worked ok. However, I am frequently asked to give her children a ride to school after mass. She usually will drop the kids off at the church. After a few times of being late, I immediately asked her to please out of respect for Our Lord, she needed to drop the kids off on time. She “promised” she would do better, etc. I even asked her to drop the kids off after mass (at least they wouldn’t be disruptive) We go to daily mass and this is a very small chapel, so that when you come in, the door squeaks. Anyhow, I have already told her how disrespectful her behavior is, but it is fallen into deaf ears. Any tips on how I can handle this in a compassionate manner besides praying for her and the family

???
You may have to tell her to make other arrangements, especially if she continues to be late. Could it be cultural? I worked and lived in Italy for a month, and it was very normal for people to just be late for everything. We were warned about it beforehand. Trains and buses were always late, stores would open late, people would never show up at the time they said they would be there. We’d be asked to show up for rehearsals at a certain time and sometimes our conductor would be an hour or two late. We just had to expect and accept that we were never going to start at the time stated. Fortunately, our stage director was American, so we just worked on staging while we waited. Although I loved Italy, it was difficult getting used to that particular aspect of the culture, coming from a culture that values punctuality.
I also grew up with it. My mother’s side, including my mother, is late for almost everything. It has nothing to do with passive aggressive behaviour or controlling issues. I believe in that regard it’s cultural because everyone I know from my mother’s culture (unless they are completely “Americanized”) is late. The joke is that if you want any of them to show up on time, you tell them to arrive three hours earlier. It drove me nuts growing up with that, as my father’s side is very punctual… coming from an extreme German-Protestant work ethic and punctuality. Imagine the opposites from my mother and father. It was the one thing my father almost broke up with my mother over when they were dating, but her positive and wonderful attributes completely outweighed her tardiness. Her lateness with almost everything has made my sister and I paranoid about being late to the point that I’m teased about feeling late if I’m 15 min. to a half hour early and my sister being teased that she feels late if she is an hour and a half early (she actually drives me nuts with that. lol!) My mother has tried very hard to be better with timing. Sometimes she’s good with it. Other times she fails. It was a lot worse when we were kids and she many more stresses and responsibilities in life. Now, she is learning to not be as overwhelmed and is better at being on time… she’s not even late for mass anymore. But work will now keep her late. My dad often has to drag her out of the office. She’s always trying to help out my father’s patients with insurance issues and doesn’t want to stop until she can get it squared away for them so that they can get coverage for certain procedures at the hospital or other offices. I always show up an hour later than when she tells me to come pick her up so that I don’t have to wait around at the office for an hour.
That all said, now that I have children, it is sometimes very, very difficult being on time. When I didn’t have children it was easy to say how rude some people were when they were late and that having children was no excuse. Boy, did I eat my words and I regret being judgmental about it. I try to plan to be ahead of the game, sometimes hours and hours earlier than needed but sometimes, even if you prepare and plan, something almost always happens. Someone throws up on you and himself, the baby has a poop explosion and needs a bath, while you also have to change your church/work clothes because the poop got all over you, the dog decides to get out of the yard and you have to find her, another decides to take off all of her clothes while you are trying to change the other one’s diaper, one decides to have a meltdown right before you leave, the dog gets into the trash or decides to chew on your daughter’s favorite toy or the dress shoes you were planning to wear to church, etc. etc. etc.
You don’t have break your friendship with this person, especially if she has other wonderful qualities and this is one of her weaknesses. If punctuality isn’t her thing and it really bothers you how late she is when dropping off her children, especially after having a heart to heart with her, then either smile and accept it or just say you can’t be available to watch the children. I wish I had more advice for you.
Edit - I do have one bit of advice… if she is usually a half hour late and you used to have her arrive at a time like 9:00 a.m., tell her that your schedule has changed and you need the children there at 8:30. She’ll then have the kids at 9:00. Just don’t tell her your reasons for the time change.