Believe it or not, you were on the right path.
I really need to write a MyTake about this and I can't find where I first discussed it, but you need to use a method that I will call for the moment the "Damsel In Distress Method" although males can use it to. I know - I did 31 years ago this coming week.
Basically, what you need to do is "go on a date without going on a date".
Here's how this works...
What you want to do is create a situation in which you get him alone spending time with you but not have it come across as a date or any kind of overtly romantic thing.
So, how do you do that?
You do this sort of thing:
"I made conversation one day by asking him for help with something. Next, I plan to offer him something like gum or candy. I want to build up our comfort with each other so that it’s not weird and out of the blue for me to invite him to hang out."
That first sentence of yours is key: Ask for help. This is a form of kryptonite for men; we are evolved to assist females in distress, so, when a female needs our help, we generally will assist.
However, when asking for help, you should immediately make it worth his while in a way in which you'd spend time with him. For instance, ask for help but, at the same time, "If you help me, then let me repay you by making dinner for you." So, in this scenario, he comes over to your house, helps you with whatever, and then you get to spend one-on-one talking while you cook and have dinner with him. See how that works? It's not a date, but, for all intents and purposes, it is as good as a date.
Let me give three examples...
1. In 1980, I was friends with this girl for 2 years. I used to help get her a boyfriend too! Well, when I was a senior in high school and she was a junior, she asked me to tutor her in physics - the class that I was an expert at the previous year. She was smart and really didn't need my help, but I was over her house a lot and so it was more hanging out than physics. One day, I said "Let's go to the laser show at Vanderbilt Planetarium." and we did. That was my first ever date, 20 NOV 1980, although I don't know if it was an official date from her perspective. Soon enough though, one day, she took the initiative and French kissed me after I leaned in to kiss her to thank her for something. After that, she said "It's about time, Vin!" I was not very secure with girls, but she was great and was my first girlfriend. She gave me my first broken heart on 01 JAN 1982.
But, think about it: She needed help. I helped. We became a couple after hanging out so much.
2. 31 years ago in August 1990, I met - really met - a beautiful girl. I met her 3 months earlier, but I assumed she was bitchy. I kept seeing her that summer at college and, by happenstance, on F 10 AUG 1990, I was alone in our school's Rathskellar. She visited me and I got to really meet her. I was smitten like I hadn't been since 1971. OK, so after doing some snooping with friends wondering if she was available, I decided I needed to act. This was not like me. BUT, this is when I came up with the date-that's-not-a-date method. I knew the restaurant where she was a waitress; it was literally a few houses away from my apartment. I also needed to know the C programming language and knew that she knew it. So, I decided to go to her restaurant and ask her to help me: If she'd help me learn C, I'd take her out to dinner anywhere she wanted. To help with my cover, I had 3 little girls who lived next to the restaurant who'd often visit me. I decided I'd take them to lunch with me when I asked this waitress for help. I went to the restaurant with the 3 girls and asked her on S 18 AUG 1990. Sweet story and it all worked out as we became a couple on W 22 AUG 1990.
She became the love of my life but she broke my heart on 12 JAN 1992 and I never recovered.
3. Watch the "Everybody Loves Raymond" episode "How They Met". I'm out of characters, so watch it.
Well, let's think about it. Do you know a particular type of gum or candy that he likes? A shared fondness for something can at least give you a topic to talk about. And adding in a "thanks for helping me the other day" can help him feel appreciated. Yes, you probably thanked him at the time, but still.
Do you consider yourself unapproachable because you give standoffish vibes, or because you feel you're social awkward, or some other reason? If it's the former, it'll make less of an impact if you're the one doing the approaching.
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Do online gaming. Or visit places that people gather and chat with strangers... something you enjoy doing. To be honest this site helps some people too. Be on websites like this. Be active within any of those community. It will give you more confidence to talk with people and build conversations.
Know the feeling I'm fairly shy aswell, But that's the best way i think anyway, If that doesn't work then it's not going to work anyway.
That sounds like a good step. Maybe try finding out an interest or two
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