In many ways, I'm still not comfortable around boys, but that's OK; I'm a guy, so I can talk from the other perspective. I've helped a number of women get to be more comfortable talking to men, and I've also had the flip side experience of getting comfortable talking to women.
Keep in mind through this whole process, whenever you're involving others, it's important to keep others appropriately informed of where you are on this process and what your intentions with them specifically are. Different people are different, which means we all have difficulty communicating with some other people, even those who speak all the same languages as we do, so somebody will probably get their feelings hurt. But by doing your best to communicate where you're at in this process and what your goals are, you reduce your risk of hurting others, and maximize your chances of keeping communication lines open when it does happen, leading to quicker resolutions.
first steps
Hanging around people like your best friend while they hang around guys is a good step one. So far, you're doing pretty well. Maybe you feel like you're a bit behind, but apart from a few special cases, I wasn't comfortable talking with women until I was significantly older.
Another good first or early step is to talk with guys online. At this stage, you don't have any long term goals with the individuals you're talking to, you just want to get familiar with it. While it may feel odd to do it, pretending to be a guy for this might make things a bit easier/less awkward. When I was first doing this, I felt nervous about it because there was so much I didn't know about how to be a woman, I felt like I couldn't possibly pull it off online.
Except here's the thing: for most online interaction (i.e. outside of an interactive audio or video environment), you can just choose to not talk about anything that would give you away. Also, different people are different, different schools are different, and so forth. Any failed interactions here are frustrating but OK, so long as nobody's hurt. You're not playing you, so anything they may say about you doesn't reflect on you.
If you can talk with your father... remember he's a guy, too. Presumably, one who knows you fairly well and is fairly protective of you. Talk with him, he may have some useful insights. I'm not going to suggest you ask him for any matchmaking help because there was never a time when I was at all open to any matchmaking help my mother wanted to provide. Considering the situation you described, this would probably need to be a phone call, but that should be fine. Of course, a lot of this would depend on your father. My ex father-in-law has always been useless at offering social guidance.
Your mother found a boy she liked enough, and also should know you fairly well. She might have some pointers for you, too. Sure, it was a very different world when she was going through getting comfortable around boys, but she's lived through all of the times between, so she may be able to translate some. Or maybe not, my mother never could. But my ex mother-in-law was able to give my ex the guidance she needed, and continued to be able to do so even through to marrying a wife of her own, which was very different of my ex mother-in-law's personal experience.
second steps
You don't have to be finished with the first steps to start the second steps. But I wouldn't have been ready to contemplate the suggestions on this list without having gained confidence from the first set. Also note that moving on to this list doesn't mean you have to stop with the first list.
There are really shy guys, too. Maybe your best friend and her boyfriend(s) could help find one for you to hang out with sometimes. This is still not an attempt to find a lasting relationship, but since it's in person, the stakes are admittedly higher. This doesn't need to be someone at your exact level of awkwardness, but just someone who is still a bit shy, and remembers what it was like to be very shy.
Babysit. Boys who are 1-14 years old are much less intimidating, especially when you're in charge. This is absolutely not a suggestion to do any more than the job entails. But once you're comfortable telling little boys what to do, and you've come to terms with many men just being big boys, the confidence you have with little boys may translate to confidence with big boys.
This is not something I was able to do much; guys really aren't entrusted with babysitting opportunities like gals are. But many of the shy gals I've talked to have told me that this helped them a lot. They did need to have a bit of confidence to start, which is why this is a second step rather than a first step.
third steps
- Figure out what your long term interests are in guys. This is not just a rough orientation question. Ideally, for this point, you can determine a type of guy that you would like to be friends with, but not want to be more than friends with them. Try to identify such a person, preferably who also doesn't have romantic interest in you, and start hanging out with them. It's fine to initially do this in the company of others, before migrating to doing it with just you and them. It's also fine to never migrate to doing it with just you and them.
I'm pretty sure I've missed a number of important options for you to increase your comfort dealing with boys, especially in the second and third steps sections. Hopefully, now that there's at least an incomplete answer on the Internet, someone will come by and fix it.
Past this point, you probably have more questions. Some of them may have been answered on IPS SE, and others may not have. Look for these questions before you ask them, just in case someone already did. But in any event, they're separate questions.
More than 20 years ago, when I was looking into how to get comfortable around women, most of the guides I came across ended with "ready to date". I knew enough people then to know that's not necessarily what you have in mind, so I'm not going to say that. I've since met enough people who found the person they were wanting to find and get to know while they were involved with this journey, possibly even as early as first steps.
As such, I'll just end with, be careful and good luck.
