Whittling is also a good one, low investment and relatively simple.

Oh, absolutely. This has always bugged me, but memes don't always follow logic once they've caught on.

I think approaching this in a level-headed, communicative way is your best option. Steer clear of openly professing your love for them, just ask them if they'd be interested in going on a date. In your shoes, I'd also make it clear that I value their friendship, and if this isn't something they'd be interested in the last thing you want to lose is a good friend. Feelings happen, handling them in mature way when they aren't reciprocated is the key to not burning that bridge. No matter how bad a "no" might hypothetically feel, not knowing and living with that regret will always be worse. On your other notes about how you see yourself, I've been there too. Clothes that fit and a nice haircut can do wonders (not assuming you don't do these things, just putting it here in case). All that aside, you clearly have a lot to offer as someone they enjoy talking to so frequently. Remember that when you ask, confidence can go a long way.