Hi Nichole,

I would:

1. Give it a year. Tell him you ARE (not “will”, ARE) dating other people. That he should do the same (as he obviously is now anyway). Tell him to please not bug you for at least a year.

2. At the end of that year contact each other (if you’ll even want to).

3. HE can move to Chicago to be with YOU this time! (This will be the real Test to see how he REALLY feels!)

4. Now that he is local to YOU, DON’T let him move in with you! That is how he got lazy and took you for granted/for a fool. This too is a test of his seriousness! After a year of being in a conventional relationship maybe there is a future there.

Obviously this may never work, but if all these things fall into place he will have redeemed himself.

Best,

Inky