Yikes. A long time ago I wrote a column with 10 basic legal truths. One was never lend anyone money ever under any circumstances, unless you’re a bank. Also, if you ignore this advice always get written confirmation of the loan, signed by the borrower. Banks call this a note. Others call it an IOU.
Your first problem is that the deal sounds a bit fuzzy with the agreement by her to go out on dates and “things like that” in exchange for money. If a court even vaguely senses that money changed hands for, shall we say, very personal services, you’re all done. Even an otherwise valid written contract can be held void for illegality.
But, if you have promises by her to pay back and you changed position in reliance on those promises, giving her your rent money, then small claims court might enforce the oral contract. Helping someone fix their car so they can get to work is one thing, a deal for “dates” is something else.
Andrew Myers of Derry has law offices in Derry and North Andover. He is a member of the American Association for Justice and the New Hampshire Trial Lawyers Association. Send questions to firstname.lastname@example.org.