OOP wants to give a big gift without making it weird

I am not OOP. This was originally posted by u/AmbigrammaticAir on r/Advice.

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ORIGINAL POST - Dec 11, 2020

My coworker recently lost his car–don’t know the details, probably broke down or something. He had to cancel his own wedding for his son’s funeral last weekend. He’s in a really shitty spot. I don’t think this guy is one of those “make someone feel sorry in order to take advantage of them” types so…

I was already kinda half-ass looking around at newer cars, waiting for a deal for a few months now but not needing one ASAP. When I heard this guy was ubering to and from work every day I was like, holy shit I’ll just go ahead and pull the trigger on a new-to-me car and give him my old car.

I have decided I’m going to do it but I have no idea HOW to do it. I want to preserve his dignity so I’m not going to make a big show of it, in fact, I really don’t like the fact that our coworkers will figure it out when they see him driving my car. I don’t feel like I’m doing it for self-aggrandizement, everything just happened to line up to where I can really help this guy. I’d have donated it to NPR because I wouldn’t get much in trade and don’t want to hassle with selling.

How should I approach this? What is the most graceful way to give this to him, and refuse payment if he offers it, and not let it be weird? I mean, I know I can only control my side of things but if there are some things I can say or do that would make it easier I’d appreciate some insight.

In my mind, I was thinking of inviting him into an empty office and just being like look dude. I want you to have this. But then… what? What if I offend him? What if he refuses to take it and continues to Uber into work? What if he gets weird afterwards? My boyfriend said I should offer to sell it to him for a super-low price so it doesn’t feel like charity, but I feel kinda tacky being like “hey I know you have all this shit going on but if you give me 500 bucks I’ll give you my car”? Nah that won’t work for me. Maybe I could offer to sell but be super insistent that I will NEVER ask him when he will pay me and he can get it back to me whenever he wants, 5 bucks at a time if he needs to but really I am not trying to make money off this. I just want to help my colleague. He’s kind, warm, and hard-working and he’s dealing with a bunch of shit. A big steaming shit pile. I can’t sit here KNOWING I can help him and just …shake him down or do nothing.

How do I even remotely handle this

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UPDATE added as an edit.

So, I showed up right as he was walking across the lot to his truck to leave for the week. I ran up and was like, “hey! How you holding up?” He sighed heavily and said “I am getting through it because I must get through it.” I asked, “Have you come to a solution for your car problem?” And he sighed again and said, “Yes, the solution is that I must have one and can’t afford another.” We were about 20 yards away from employee parking and could see both my cars so I said, “Well, this weekend I bought that car (point at new car) and so now I would like you to have that one (point at old car).”

He was absolutely speechless, so I kinda started talking fast and was like “I couldn’t find the title–it’s in my closet somewhere–but I have all the necessary paperwork you need to bring to the Iowa DOT to transfer it into your name. I’ll pay for a replacement title if I can’t find it, and it’s overdue for an oil change so I’ll get that done this week while you’re out too. I’ll leave the keys on my desk so you have them if you get back after I leave on Friday.”

I attempt to look in his eyes but his mask has fogged his glasses. I continue.

“Yeah, they only offered me 98 dollars for the car and I didn’t think it was worth it and I didn’t really want to hassle with selling it online. Also I don’t have space at home to keep it, so I thought to myself, why not let [coworker] have it? So here we are.”

He has begun shaking. It’s 15 degrees so I am getting pretty cold at this point and I start hopping a little.

“So…would you take my car please?” I ask, by way of concluding the offer and requesting some kind of feedback.

Immediately, he grabbed me around the shoulders and pulled me in for a long, strong hug. He is openly weeping into my hair now. He is saying something but my scarf is muffling his words, but I let him hang on until he decides to pull back. Finally he removed his glasses, and he looked me in the eyes and said, “You have changed my life with this gift. I cannot describe what you have given me.” So of course I started crying and we hugged again. Then, he said I must be freezing and I am to go into the office immediately, so I did. He sat out in his truck for a while before finally leaving for the week, and I feel content that he did not insist on haggling over money. Perhaps if he decides later to bring it up, I will entertain what he has to say, but for now I am well satisfied with how this turned out. Now I just have to find that damn title 😵

I want to say thank you from the bottom of my heart to each and every one of you who read this and took the time to reply.

As it turns out, I was totally overthinking how this was going to go!

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Reminder: I am not OOP.