I feel it’s like if a person is walking down the street and sees a twenty dollar bill on the sidewalk. I feel there are some people who would think “Great. I’m twenty dollars richer.” And some people who will think “Somebody lost twenty dollars. That sucks for them.” And most of us would probably think some combination of those two feelings. But I don’t think there are very many people who would think “Great. I’m happy knowing somebody lost twenty bucks.”
That makes no sense. You’re talking about strangers (in fact, people who never even see each other).
I agree with little_nemo that thoughtlessness seems a lot more likely than malice.
Think what you like. I don’t care. I know what I’ve seen and experienced.
I’ve already said it’s rare.
There are a disconcerting number of people who just don’t (can’t?) consider any point of view but their own. Sure, you’re going to be inconvenienced, but that has no bearing on the fact that she wants something.
Without reading the entire thread, this is what I suggest.
I have a lot of close relatives who will suck you dry if you let them, and you have to just be firm.
Most of us are socialized to not turn down requests, because we also are under the assumption that people won’t make requests until the other person really needs it.
However, moochers are breaking the unspoken rules of society and you have to set limits.
As @puzzlegal says, the best way is to simply decline all further requests because she’s not going to be reasonable. You absolutely don’t want to get into negotiations with her, because she’ll be constantly trying to bend the rules and the mental energy isn’t worth it.
Frankly, when someone becomes irresponsible with their primary plan being to mooch rides from you, then they need to be cut off and set free.
Also, quoting for truth:
Yep. There are a number of different possible root causes for this whole thing and (IMO) the only thing that’s likely to work for all of them is to yank the issue out into the open and discuss it like grownups. It’s likely to be awkward, possibly painfully so, and it might trigger a complete and undesirable change in the relationship, but adding layers of passive-aggressiveness, hints, excuses and other weird behaviour just means you’re becoming part of the problem rather than the solution.
OP, in my lifetime I have vacillated between being honest/direct and avoiding confrontation. In those moments when I’ve been true to myself, I have always left the interaction holding my head high and feeling content. In those times when I have scuttled my true feelings, I have always felt pangs of regret.
That is not to say that confrontation is comfortable. Even polite confrontation can be very awkward and unsettling. But I agree with the general consensus of the thread that you do not need to be this person’s rideshare, and should set boundaries that you are comfortable with. (Actually, my advice was going to be “ass, gas, or grass, nobody rides for free” but I see somebody already beat me to that).
My suggestion is to think of the sentences that most directly convey your feelings. Practice them. Perhaps you want to say “I am sorry, but I’m just not going to be available.“ Or if you feel like you need to provide some explanation, you could say “I’m trying to be really frugal right now, which means I am avoiding using my car for trips that I do not need to take. So I must decline the request.“
Or, as somebody already said up thread, no is always a valid answer. Remember, too, that “No” is a complete sentence. You can say it and just wait for the other person to reply.
Once you’ve practiced your declarations, it might be easier to have this conversation over the phone. In that case, I’ve found it’s easier to discuss uncomfortable topics if you are walking around as opposed to sitting down. And you might try closing your eyes when you say the confrontational parts. For some reason, it might make it easier to articulate your feelings.
What I am almost certain of, however, is that whatever confrontation you have with this neighbor will not be as uncomfortable or difficult as you fear. In my experience, it never is. My anxiety about confrontation is always worse than the confrontation itself.
As such, if you do have this discussion, I anticipate that you will update the OP with some positive news about your situation. Either the neighbor will have found another ride, or you will have a better understanding of why the neighbor is asking you for your help. Or, the neighbor will start to reciprocate with some favors.
Good luck!
I long ago decided to be direct and honest whenever possible. That way, if someone dislikes me or my actions/position, at least they are disliking the correct thing!
A tremendous percentage of people view directness as being rude or mean. That’s their problem.
If this happens to you a lot, you might be doing it wrong.
I think part of the reason for that is: a lot of people use ‘I was just being direct and honest’ as an excuse when they were actually just being an unnecessary asshole. Like blurting out the unsolicited opinion “Hey your eyes look like piss holes in the snow”. Doesn’t matter if it’s honest and direct and truthful. It’s also unkind, unhelpful and unnecessary.
That said, I think the OP’s situation does require an honest and direct approach, just tempered with a little diplomacy. Just because, until OP has that conversation, they are not dealing with the real actual problem - they are instead dealing with what they assume to be the problem.
I find merit in this observation. I’ve seen it in action more often than I wish. Some people consider it a personal affront just to be told no.
My father is such a person. One incident stands out in my mind: We were visiting Ireland and chanced upon a small but high quality jewelry store. My father is a jeweler. Of course we stopped in and my dad struck up a conversation with the owner.
At some point, my father proposed they do some business together. The owner was obviously well fixed and didn’t need to create any additional partnerships. He very politely declined my father’s offer.
The whole rest of the trip, my dad never stopped complaining about what a rude, awful man the owner was. How abrupt and disrespectful he’d been. To this day, if he relates this story, the store owner was a bastard.
“Hey, Dad. I was there. That’s not how it happened at all.”
All the man did was say no.
There’s a quote from somewhere, “People who say they are brutally honest are more interested in the brutality than the honesty.”
I’m talking about something different. People seemingly not wanting to express an opinion or preference - even tho they have one. Instead, they want YOU to read their mind and come up with what they want as tho it is your idea.
Or people not wanting to express an opinion - or even answer a simple yes or no to a yes/no question, because they want tho be able to change their mind, they fear someone else will dislike their answer, or they think vagueness helps reach consensus.
People excessively use qualifiers, in a hope that they will make their opinion more palatable, in a way that interferes with effective communication. I really dislike having to guess how to interpret ambiguous statements - about subject matters which are not overly complex or nebulous. Or having to ask a series of follow up questions to get at the direct answer that could have been given initially.
Yeah, I admit I’m not the most sensitive person. I’m comfortable that I do not intentionally say things in a way intended to make someone else feel bad. But I place a high value on clearly expressing what I wish to say. If what I wish to say is of less value that avoiding making someone feel bad, I do my best to keep my mouth shut.
I heard something like that from a psychologist friend who was kind of obsessed with the idea. He contended that when someone says, “I’m going to be (brutally) honest with you…”, it’s often a kind of sociopathy.
About dealing with abusers, tact is important, especially insofar as giving the abuser some wiggle room to save face.
There was a coworker who asked for work-related favors often enough to be abusive. Knowing I was the new guy, he’d try to get me to do things that would make his job easier. Once I realized what was happening and was able to determine that it was indeed abusive, I said something like, “It looks like you’re trying to get me to do your work for you. I must be mistaken, because a good professional like you would never do that.” He agreed that it was a misunderstanding, changed his story in mid-stride and never asked me for another favor.
That’s fair enough. I merely wanted to offer an explanation for why people might consider directness as rude or mean. It’s possible they have experienced abuse from people who claimed to be direct, but were just using it as a way to excuse themselves being rude and mean. It’s unfortunately common.
Or they may just have a victim complex like @Aspenglow describes.
One has hope. 
At least where i live, it used to be impractical to take a cab, because there weren’t many drivers and the experience could be quite unreliable. But now, with ride-share, it’s extremely easy to catch a ride from the shopping district to my house or vice versa. Unless Mary is too phone-illiterate to manage that, she’ll be fine.
I give friends rides if we are going to the same place, or if the drive is long enough that i don’t really want to drive on my own, but more and more when i offer to arrange a ride for a carless friend to visit me in my not-super-accessible location, they decline and say they’ll catch a Lyft or Uber.
Well, not that I think anyone is desperate for an update from me…
I had a (hopefully effective while still being nice) conversation with Mary this morning. She called, asking for a ride tomorrow, and the first thing I did was ask her exactly where she needed the ride to. She hesitated a second, as if startled, so I went on to explain that I’ve been blowing way through my allotted gas budget lately, and so I’ve decided I’m not going to give people (yes, I said ‘people’ not ‘you’) rides to anywhere outside my home town or maybe a neighboring town, except in real emergencies. “Like, you know, you’ve sliced open a finger and it’s gushing blood.”
She said, “Oh.” A little pause, then “I just wanted to look at the flowers at the Nursery, I always buy some chrysanthemums for my porch in the fall.”
I said, “Oh, that sounds nice, and the Nursery is only a couple of miles away. Let me look at my calendar,” I set the phone down kind of noisily and walked away for a moment, then came back. “I’m going to be going to the “How to Declutter” lecture at the Elder Housing Complex on Wednesday which is right around the same area. It’s at two pm – how about I pick you up about 1:45 and we go to the lecture and then hit the Nursery on the way home. How’s that sound?”
“Um,” she said. “I guess that’s okay, if they’ll still have lots of chrysanthemums so I can get the colors I want.”
“Fall is not even really here yet,” I said cheerily. “I can’t imagine they’ll be sold out. So I’ll see you Wednesday then. But do let me know if something comes up and you can’t go, right? Bye!”
So, 1) I’ve flat out told her no more non-local rides. 2) I’ve raised the point that gas costs money and I don’t have it in unlimited amounts, so maybe she’ll get the hint this time. 3) I made the point that I plan to work her trips to mesh well with my own activities. 4) Guess what? Having to around for the other person’s activity can go both ways.
I’m feeling rather pleased with myself – I managed to make my points clear, I think, without having to be rude or confrontational. I genuinely don’t mind giving her the occasional ride, I just don’t like her treating me without consideration for what I might need.