My boyfriend was laid off from his job two years ago. At first he lived off his savings and 401(k) but when that ran out his father offered to give him money to pay his bills and not lose his house. For the first year his father also lived with him but for the second year his father has been in Assisted Living (after having an accident that left him needing more care than he could get at home). His father has continued to give him money though. His father receives a pension & social security which pays approximately 65% of the Assisted Living bill each month and he pays the balance from his savings. However, that money is running out. If he needs to apply to Medicaid to pay the difference on his Assisted Living (or eventually Nursing Home), will he be penalized for the money he's been giving to my boyfriend to help him out? They both live in Connecticut (not sure if that makes a difference). Would he even be eligible for any Medicaid since he gets a pension & social security?