For example, I found myself in an uncomfortable situation with a neighbor in regard to shidduchim.
I wasn't sure if I handled a situation properly, with proper respect & derech eretz.
I asked my husband & someone else, both of whom said I handled it just fine & the neighbors understood just fine, no problem.
I wasn't so sure.
Unfortunately, based on the dynamics & personalities involved, it was a situation in which apologizing or even just asking about the issue could make things worse; bringing it up could create a problem that, for the moment, existed only in mind.
So I spoke to Hashem about it a couple of times, requesting that He enlighten me about what I needed to do (if anything) and whether the situation really lay at rest or not.
I didn't invest hours of hitbodedut in this; just briefly explained my concerns & doubts, and asked for help, for a sign one way or the other.
And I did this only a couple of times.
The first happy indication occurred when I went to knock on another neighbor's door to request something—and right then, the married daughter of the neighbor (about whom I felt concern) came down the stairs with her young children.
She greeted me with cheerful warmth, giving no vibes of coldness or hesitancy.
This was the first sign that as far as this young woman went, everything was fine.
(The situation primarily involved her & her mother, so the fact that Hashem brought us to the stairwell at exactly the same time showed me how much He cares & orchestrates things to the second.)
But still unsure how my neighbor felt, I briefly asked Hashem again to help me figure things out.
A knock on the door Rosh Hashanah morning brought me face to face with that same neighbor. She held a platter of homemade dairy delicacies, which she handed to me with a gracious smile & a warm wish for a good year.
Thank you, Hashem—thank you for both the reassuring answering to my quandary and also for all the lovely cheesecake & alfajores!
Later, she sent her teenage daughter with a platter of succulently prepared meat, chicken, and rice.
What a delicious relief!
Why This Works for EVERYONE
We don't always know.
And that's okay.
Sure, the problem might lay within ourselves. Maybe insecurity, overanxiety, a sense of over-responsibility, and so forth.
But maybe not.
While society is quick to label such a person as "overthinking things," "overanxious," "co-dependent," "needy," "obsessive," "neurotic," "too sensitive," and so on, you are who you are & whatever level you happen to be on now.
And you need to deal with yourself where you are right now & sort things out in a way YOU can understand.
Side point: I also noticed that simply calling people names—including psychology labels—has never been helpful. It's not like people who, say, overthink things magically stop overthinking just because you tell them. Most people need help & strategies to overcome a behavior, and not just be told, "Here—this is what's wrong with you."
And that is indeed if there is actually something "wrong" with you, and not just that the other person finds you annoying because he or she resists thinking about others or examining their own behavior, and therefore accuses anyone who does of "overthinking things."
Reaching out to Hashem & saying, "Help me. I don't want to be a source of pain for another person. Please show me the truth of the matter"—this usually brings an answer because THIS is one of the things Hashem wants most.
He wants us to be nice to each other—sensitive, compassionate, and caring.
Hashem also wants us to make amends when we've stumbled.
It's important to know that Hashem helps regular flawed people, as shown above, and even without investing hours of prayer in the issue.
Sometimes, people don't bother trying because it seems too confusing or too complicated, or too much trouble.
And yes, sometimes it IS pretty confusing or complicated.
But before dismissing something as too confusing, complicated, or too much trouble, it's worth turning to Hashem as you would a truly trustworthy Best Friend, a Best Friend Who can & wants to help you with anything & everything.
Just a few brief words, expressing, "I feel bad about this, not sure if it's just me, and not sure what to do about it, but would really like some kind of indication how I'm supposed to proceed. If everything really is okay, then I'd like to know that for sure. If everything is not okay, then I'd like to know what's wrong & how to fix it."
So I didn't invest in the conventional methods to work out the above issue because I needed to know FOR CERTAIN, and no method was going to give me that certainty—except asking Hashem for help.
And I'm far from being on a high level, so I don't deserve direct intervention, but Hashem gave it to me anyway because He truly helps us do the right thing.
He's Compassionate like that.