In the following days, he made it clear that he wanted to continue to see me and I realized his strategy would be to woo me with his money.
Playing it cool and not getting too involved may make you feel safe, but you risk coming across as aloof or remote, and may turn the other person off.
You want to get to know the person and each have a chance for a fresh start.
Carrying old baggage into a new relationship amounts to clutter.
So if you want to keep something on hand, go with a classic gift that says, "Thanks for giving me something to do this Valentine's Day so I didn't have to sit at home by myself." A cool bottle of his favorite booze, a Netflix gift card, or a book you think he might like are harmless yet amazing gifts for anyone, really.
And of course, it wouldn't be Valentine's Day without candy, and chocolate bars are definitely dude-friendly.