what text messaging app are you using?

 

I've never had texts break at 140 characters, and I've never long-pressed on anything. Admittedly I also don't use Google's Messages app, so it might be worth trying a different app, though SMS should be SMS regardless of what app you use.

When you say you have this problem when texting "non-Android phones" is that a code for iPhones, or does it include dumbphones as well?

The subject line mentions MMS, and some apps have a setting to send long messages as MMS. If Google's app doesn't have that then it's definitely worth trying a different one (the apps I've used in the last few years, which included Textra, Chomp and QKSMS, all have that). Though I'll note that I've never used this option (SMS are free, MMS are **** expensive with my carrier, so I don't use MMS for anything ever).

For the record I'm using a Pixel 2, currently Android 11.

 

I've never had that problem either...but I do receive some that way for iPhone users sometimes.
Join the Beta for messages & use RCS.

BTW: using Signal as of late.