This is an archetypal symbol! Jumping off the cliff...it symbolizes beginning anew. In tarot the Fool jumps off the cliff - he takes a risk - he may end up looking ridiculous or divinely inspired and genius for taking the risk he's taking - starting a new life a new cycle a new phase. The Fool embodies Uranus (FREEDOM to be who you truly are!!!) - which seems very apt for your man (what you've told us about him and freedom etc). He desperately wants to take the leap with you (leap of faith - as nothing is solid - there's no solid ground when you leap!) and perhaps in the beginning he felt like he was.....now it sounds like he's put the breaks on...but if Uranus is hanging around his chart...he might leap yet! He's not around 40 years old is he? (big Uranus transit where you want to leave everything and start anew - totally rebellious and 'expect the unexpected')

Very interesting...!

love T