Came here to recommend this podcast (or his books https://www.amazon.com/Discernment-Spirits-Ignatian-Everyday-Living/dp/0824522915 but the podcast is freeeee.)
> However, short of visions and deep meditation, how can we actually measure our personal relationship with Jesus if not by an emotion or intellectual stimuli?
St. Teresa of Avila (who is a doctor of the church and a good resource on mental prayer) says that the way we judge this stuff is by looking at whether we love our neighbor (if we "love God" but this love does not overflow into caring for our neighbors, we're probably fooling ourselves), and whether our prayer life is bearing fruit in good works. Very concrete and fairly objective. Our prayer life could be totally dry and painful, and a fight against boredom and distraction every time, and we could still use this way of judging whether it is bearing fruit. Prayer changes us; a close relationship with Jesus changes us; at some point this will even be evident to the people around us whether we want it to or not.
The emotions we feel in prayer and so on are "consolation" (this is a gift from God and it's up to Him to decide whether it is good right now for us to have it); I recommend having a look at https://www.amazon.com/Discernment-Spirits-Ignatian-Everyday-Living/dp/0824522915
> and the ongoing dialogue I thought I was continuously having with him?
Anything that you thought you were saying to him, certainly you were saying to him; and certainly he was listening to you with love. So, half of the dialogue, we don't need to worry about. As for the other half, sometimes we imagine things, and sometimes we have what I would call "a holy imagination" like when we imagine ourselves in a scene in the Bible (God can speak to us through our imagination and inspire helpful feelings or helpful thoughts even though it is in fact our imagination), and sometimes maybe God speaks to us fairly directly, but I would not spend a lot of time fretting about which of these things is going on; I would measure everything by the same yardstick as I would if I was sure "this is me deliberately imagining a response": does it help me to love God, to serve God, to love and serve my neighbor; is it in accord with the teachings of the Church; if it is not helpful or is in conflict then discard it.
> It's perhaps important to note that I've had this 'want' to kill myself, since I was a kid.
I agree that's important to note. If you are not getting help for it yet, get screened for depression by a medical professional. Our mental health impacts our spiritual life, more than we give it credit for (just like physical health and mental health affect one another.)
> what does it mean to love God? I don't know. I've tried,
That is a good question.
If we experience spiritual consolation (this means enjoyable feelings in prayer or while doing religious-type things like going to Mass) then it's very natural for us to have warm feelings towards God and to feel happier about the idea of praying or going to Mass. It is like, if I eat a healthy meal, and I was hungry, and it tastes good, and I feel good after I ate it, then I feel more like I want to eat healthy and it is easier to form a habit of eating healthy meals.
If we are often depressed or if our lives are difficult or if we are in a "dry spell" where we do not experience spiritual consolation in prayer, then it is like eating a healthy meal when we know we need to eat but aren't feeling hungry (because we have been ill, or have been under a lot of stress, or have not eaten in long enough that the feeling of hunger stops) or when food does not taste good to us (because we cannot smell properly right now, or, some other list of reasons). It is a lot harder to get yourself to eat properly then.
One way that we can "love" ourselves is to make sure that we are eating the right kinds of food often enough, even if we do not feel like it. I put love in quotes because this doesn't feel like the way we expect love to feel. (Eating a slice of chocolate cake feels like the way we expect love to feel.) And one way that we can love God is to do the things that we ought to do, even when we do not feel like doing them.
It is more fun to do the things that we ought to do when we are getting enjoyment out of it. Usually, we are doing those things partly because we do get enjoyment out of it. Someone who feels "in love" with someone else does not mind doing tedious or unpleasant things for them, because they are feeling this "in love" feeling; but, at other times in their relationship, they might not be feeling that way, and might have to force themselves to do those same things.
So in fact you have been loving God, because you have done these things that you listed without the spur of "I really enjoy doing them and have warm feelings towards God". Keep asking God for help to do this (we are literally not able to do it without His help, so, He has been helping already). Do what you can to take care of your mental health as well. If there are things that make you happy (e.g. maybe being outside in nature lifts your spirits), do some of those things and "invite" God to be there with you (He already is, so this is simply a matter of remembering that He is with you, and talking to Him a little bit about how you are feeling.)
For more about consolation and desolation, see https://www.amazon.com/Discernment-Spirits-Ignatian-Everyday-Living/dp/0824522915 (or the author's podcast series at discerninghearts.com if you prefer audio or prefer "free".)
Maybe you are talking about consolation... it's a thing that can happen, but it's also normal for it not to happen.
I recommend reading https://www.amazon.com/Discernment-Spirits-Ignatian-Everyday-Living/dp/0824522915 (if you don't want to spring for the book, the author has a free podcast series on discerninghearts.com )
If you have not read https://www.amazon.com/Discernment-Spirits-Ignatian-Everyday-Living/dp/0824522915 I recommend it to everyone.
> With almost no prompting I started remembering sad and hurtful events with friends/ family in deep and exquisite detail.
There are multiple reasons why this could happen (natural or supernatural) and the reason is honestly not that important. What you do next is the important thing.
When something like that happens I try to turn my attention to the Passion, e.g. think about one of the sorrowful mysteries of the rosary or something in the stations of the cross or just being figuratively stabbed in the back by one of his closest friends (Judas was an apostle and had been through a lot with him) and hearing Peter lie about having never even met him. Jesus knows what it's like to suffer, whether physically or on the inside. If we are thinking about him suffering (innocently, and to save us, when we don't deserve it) then we will stop being sorry for our own selves or angry at our own experiences and we will love him more and feel compassion for his suffering.
> And it’s hard to explain I just felt this deeply angry and disappointed presence as if some invisible force just really didn’t like me.
Demons are real and they hate us. Realistically I feel like it's safe to assume we're always under some kind of attack and it is just the type (and obviousness) that varies.
However, they are also chicken. (In any case the only thing we should be "afraid" of, in this life, is our own ability to choose to commit sin.)
In a moment like that, I would say a Hail Mary (if that's not your cup of tea, call on God for assistance in whatever way is normal to you, e.g. the Jesus prayer, or make the sign of the cross which is itself a prayer). St. Teresa of Avila (who has earned my trust, YMMV) said holy water was very effective and I now bring a little squirt bottle of it in my purse if I am going somewhere where I am likely to need it. I holy-watered the painted "buffer zone" stripe on the sidewalk outside Planned Parenthood when I was there yesterday at a prayer rally thing (not at Philly but in support of that one), because of reasons.
Fr. Timothy Gallagher, author of Discernment of Spirits also has a podcast on the 14 Rules of St. Ignatius of Loyola and many other related topics worth checking out here. The rules are definitely beneficial, I highly recommend the podcast if you're not sure about where to start.
If you would like an Ignatian approach there are a couple of good books (choose whichever seems to fit your case better)
Sometimes God does allow the enemy to put obstacles in our path; these could be adverse circumstances (things that we might call "really bad luck"), or these can even be feelings of fear or aversion or that it is hard to take the step to do something (there is an example of this in The Seven Storey Mountain) when there is something that we know we ought to do.
We are all also supposed to discern whether we are called to a religious vocation (when considering careers) so if you have skipped that step then I would give God a quick "hey let's get this out of the way" question about that.
Ok. I will give some general advice.
I recommend https://toptalkedbooks.com/amzn/0824522915 to anyone who has gotten more serious about the spiritual life.
> My trust with God has been steadily deteriorating since this time last year.
You go to daily Mass, you cry "God help me", you ask the Blessed Mother for help. These are good things. It might feel like these are not doing any good. That would not surprise me. They have an effect, but we are not always given a sense of what it is (we can really only sense natural things, and if we do sense something else, like consolation or peace, it is because God wills us to sense it. It is not like Spider-Man, who always has a spider sense which belongs to him. Rather, each time it happens, it is a gift and not a thing that belongs to us, and we should expect that sometimes we will not have it.)
God likes for us to learn to trust him more. What he really wants is for us to trust him enough to have a total, child-like dependence on him, the way that Jesus in the Gospels has total filial trust in the Father (in the saints you can see a lot of variety in how this looks: we might look at an extravagant example like St. Francis, or a subtle example like St. Therese of Lisieux.)
Grace builds on nature, and by nature the way that we get better at something is through practice (which is fatiguing and slow). The way that we get better at trust is by being out of our depth. I remember my father teaching me, in a swimming pool, how to float on my back. It was not possible to learn how to do that while feeling totally safe (you have to have enough water under you to float in, and it feels like this is also enough water to sink in, and even though your dad is right there you are nervous), and it took some practice. I do not like to float on my back because I get water in my ears and I do not like how that feels, but I do know how to do it, and I know that it's necessary to be very patient when teaching someone else to do it.
When we are thrown into a situation in which we can no longer feel totally independent, totally self-reliant, and able to cope with everything without God, then it is very upsetting to us. It is like having to step out onto a bridge that is a sheet of glass: we can't see that there is anything holding us up, there isn't even a railing to hold onto "in case". Even when we are more used to "having to" trust God more, we don't necessarily like it, any more than I like having water in my ears.
Society says we should be self-reliant, and so we might (unjustly) question our competence or our worth when times get hard or things fall apart. People who hold to the "prosperity gospel" (and some kinds of atheists) say that if someone has misfortunes it must be because they deserved it (just like people asking Jesus "why was this man born blind - was it because of his sins, or because of his parents' sins" even though there were already teachings that that's not how it works.) So we wonder "what did I do to deserve this".
If someone has turned away from God, encountering difficulties might be a wake-up call, and this is why I asked first about prayer. For someone who has not turned away from God, difficulties in life are not a punishment, but an opportunity (I can't help thinking of a friend who used to work for a large company where there was a rule that you couldn't say "We have a problem" in a meeting, you had to say "We have an opportunity", to encourage positive thinking I suppose - but instead people said "opportunity" in the same "this is really bad" tone of voice that they would have said "problem", lol.) I think actually we are supposed to be thankful for difficult times (in the Mass after we say "it is right and just" the priest usually say something like "it is truly right and just, our duty and our salvation, always and everywhere to give Him thanks") since even things that suck are part of "always and everywhere", but right now that is, as they said at my previous job (for the type of quarterly goals that we knew we weren't going to hit), "a stretch goal" and we have to learn to walk before we can run.
When someone has many trials, they should also keep an honest eye on their mental health, since maybe clinical depression will be added to their stack of trials, and should take care of their physical health (mental, physical, and spiritual health are all interrelated somewhat and affect each other, which should not surprise us since we're not made of water-tight compartments like a submarine), eat regularly, sleep enough, get some sunlight and exercise, the basics. First things first: get a job that you feel ok about, make sure you have a place to live that you can afford, reach out to people you know so that you have a support network, do not worry about the perfect lives of your secular friends (everyone has a turn to have their life fall apart at some point.)
https://toptalkedbooks.com/amzn/0824522915 is worth reading.