Gaining

I say go for it! I weigh about 370 pounds and I'm loving it. Yeah, the concern about what other people think is definitely a thing, but if you learn to love yourself and put yourself first, you'll find that it doesn't last that long.

You have to go with your gut I also struggle with worrying about what others think, but have let myself get up around 250 lbs to enjoy food and fattening without reaching a size that would be very concerning to some of my family. I have dieted down (like right now) but usually just get fat again... it would probably be better to just stay fat... certainly more fun. Maybe try gaining a bit more and see how you like it. Usually others are not thinking about your weight nearly as much as we imagine. Plus they have already seen you chubby.

If you always worry about what people think, then I say no, you should not gain.