How should one ask the Lord if someone that has recently come into your life has done so because it’s part of His plan? I’ve recently had a few encounters with someone that I find very engaging and who always wishes me a Blessed Day (that’s meaningful, significant I think, as a Catholic). I don’t know if these encounters are part of His plan for me or just random.
Any specific Saints that I should pray to, or prayers to the Lord that I can ask for guidance?
This is tough. I believe God has put so many amazing people in my life at the right time (or sometimes a later point if I missed them the first or second time around ; )
Here is a story, which is why I say that it can be tough.
When we were kids, my Mom took my two Brothers, my little Sister, and I to our local diner. While we were waiting on our food, my Brother pointed out the window at a man with a white beard and excitedly shouted “Santa!” My little Sister turned and looked and whispered to herself, “Saaaaanta.” Our food came and we thought nothing more about him. When it came time to pay, the waitress told us that it had been taken care of by “Santa.”
Now my Mom is not the type of person to let the kindness of a stranger go unnoticed and so she became Angela Lansbury and set out to find out who this man was to thank him. She discovered that he was a truck driver from the other side of the Country. She got in touch with him and this was the beginning of a strange time in my life.
He introduced my Mom and Step-Dad to a young woman who had just got out of an abusive situation. We found out later that this single Mom of two was a strıpper, which is where “Santa” had met her. This girl started coming around our home to use our swimming pool and my Brother (a Freshman in High School) took a liking to her (of course he was too young for her, but he’s always been a dreamer ; ). He began watching her two boys while she would go to work. My Parents thought God had orchestrated all of this, from encountering “Santa” to meeting this girl in need, so that they could help her. They began inviting her to their Presbyterian Church on Sundays. And they helped her get a better and more respectable job.
But, I say it was a strange time in the life of our Family, because it turned out that this truck-driver had a Wife back home that was dying of the “c” word, while he is hanging out at strıp clubs and greasy diners! My Brother was play wrestling with a strıpper in our pool. And my Parents were acting different during this time as well. My Mom started dressing a little different, but I don’t know if it was because my Step-Dad was in a Rock Band or because they were hanging out with this girl.
Eventually, the girl and my Parents went their separate ways. She had gone back to her abusive ex and life went back to normal, as if this time had never happened (or at least this is my recollection of this time in my adolescents life).
Did God put “Santa” in our lives for some reason? Did he introduce my Parents to a girl who appears to have made many poor life choices in her life? We won’t know on this side of Heaven, nor may we ever know.
You have the right idea. Talk to God and ask Him for guidance. And discern whether this individual is taking advantage of you or if they genuinely need a Christian hand to lift them out of their situation. It is difficult sometimes to know the difference. St. Padre Pio was believed to be able to know the hearts of men, before they even confessed to him. Maybe Pray to St. Pio for his Prayers and friendly insights on the matter. And know that I too will say a Prayer for you.
Thanks, I’ll pray about it including to Padre Pio.
Cade’s suggestion is good. Maybe ten years ago, I started chatting with a woman while we were waiting for the shuttle bus after work. She is a devout Baptist. We were bus buddies but became good friends. We pray for each other and our families, and she came to my wedding five years ago, and her son took photos and recorded video of it, and now my wife and I are friends with her. We are all sure that God put us in each other’s life. As for my wife, I met her through Catholic Match. We both were widowed. God certainly brought us together, and in marriage prep we had to answer a lot of questions and learn about warning signs (we didn’t see any, but one of them was “Does he leave things where you can’t find them?” and I said, “No, he leaves things where he can’t find them,” and I told her that after we married it would be her job to watch where I leave things 
)
Another thought: the Quakers, Catholic Workers, and Franciscans (and others I am sure) make big decisions as a group. An actual example is whether to offer hospitality to somebody, as in the case of Cade’s family. If a group makes a decision together and assumes responsibility together, it makes the decision and its results more manageable. This may not apply to DCM’s case, but there may be one or more wise people available to consult. When I started looking for a companion for the remainder of my life, I talked with a mature Christian man I knew and respected.