I'd rather see him with Natalie Portman.
Me, too. But alas, despite his attempts at courting Ms. Portman, she apparently did not respond.
I don't have much problem with Reese. IMO she's just really white-bread boring and probably on the rebound.
As for a woman with children, there is a critique.
I think Jake needs someone whose focus is on
him for once. His love life has been rocky to non-existent, filled with alcohol-addled party starlets or dates that went nowhere. It would be nice to see Jake with someone who really appreciates him and puts his needs and wants first as he will put hers. As a mother, Reese's children will - rightfully - always come first in her life and any man second.
This is always a problem when dating people with children. You will never be first in their lives.
Jake is still young enough that he can find a woman without the additional baggage of someone else's children. Finding love is hard enough without the add-on stresses of instant families and ex-husband/fathers.