run this to fix that: RUBY_CONFIGURE_OPTS="--with-openssl-dir=/usr/local/opt/openssl" asdf install ruby 2.2.4

gistfile1.txt

ruby-build: using openssl from homebrew
Downloading ruby-2.2.4.tar.bz2...
-> https://cache.ruby-lang.org/pub/ruby/2.2/ruby-2.2.4.tar.bz2
Installing ruby-2.2.4...

WARNING: ruby-2.2.4 is past its end of life and is now unsupported.
It no longer receives bug fixes or critical security updates.

ruby-build: using readline from homebrew
^[[A
BUILD FAILED (OS X 10.14.6 using ruby-build 20191102)

Inspect or clean up the working tree at /var/folders/y6/bxn_d19d6vv0zfhg0xm6f5xr0000gq/T/ruby-build.20191108135610.63235
Results logged to /var/folders/y6/bxn_d19d6vv0zfhg0xm6f5xr0000gq/T/ruby-build.20191108135610.63235.log

Last 10 log lines:
installing capi-docs:         /Users/joelarson/.asdf/installs/ruby/2.2.4/share/doc/ruby
The Ruby openssl extension was not compiled.
ERROR: Ruby install aborted due to missing extensions
Configure options used:
  --prefix=/Users/joelarson/.asdf/installs/ruby/2.2.4
  --with-openssl-dir=/usr/local/opt/openssl@1.1
  --with-readline-dir=/usr/local/opt/readline
  CC=clang
  LDFLAGS=-L/Users/joelarson/.asdf/installs/ruby/2.2.4/lib
  CPPFLAGS=-I/Users/joelarson/.asdf/installs/ruby/2.2.4/include
./init: line 77: ./install: No such file or directory

I had to switch to openssl@1.1 with homebrew in order to install ruby 2.7.6...after installing it, unlinked 1.1 and linked openssl 3...it's like asdf is not taking into account the flags I have set in my .profile, no issues using rbenv.