I am having this problem too. My mom's watch came last week and we set it up. My watch came today and I set that up. I am in her friends list and she is in mine. On her watch when I tap on my name the digital touch hand icon does not appear. On my watch under her name the digital touch icon is there but she doesn't receive anything. iMessage is working both ways correctly. I signed out of iCloud, iTunes, turned off face time and iMessage, unpaired both watches and then did a reset network settings on both phones. Then I rest both watches. I then turned on both phones, logged in to wifi, turned Bluetooth on, signed in to iCloud and iTunes, and turned iMessage and FaceTime back on. Once I was signed back in to everything I re-paired the watches and set them up as new watches (vs setting up with the back ups). I called Apple Care and told them everything I've done and they said I pretty much covered everything and they feel that the problem is with my mom's watch and want us to send it in for repair. I'm a little hesitant to do that because the iCloud and iMessages on her phone are working just fine. Additionally, after all of this pairing and unpairing her maps no longer show her current location or directions, and that was working before all this. Oh! Also, I deleted all messages between she and tried sending new text messages everything was fine there. I also deleted me as a contact on her phone and removed myself as a friend in the watch app. Then I readded my information with only my mobile number Apple ID email address and mailing address only. Didn't change anything when I added my new contact to her friends in the watch app.
Has anyone else experienced an Apple watch not detecting other users with watches and therefore not showing the digital touch icon? My dad's watch should be coming in June and he's really excited about being able to send sketches and heartbeat to my mom. He travels a lot for work and wants to send his heartbeat every night 😉 they're silly in love with each other even after 46 years! So, this is something that's really important for me to figure out for them!