Just because you've locked down a beau on Valentine's Day, doesn't mean your life is all red roses and lingerie - there are still serious challenges: First, picking a gift that best reflects how long you have been together. Translation: where are you on the relationship scale from socks to whiskey rocks to hoverboard?!? Second, remember that the thought counts more than the money spent. So if he has a super sweet tooth, the retro V-Day candies could be the best gift out there! Third, remember any clothing you buy him is free reign for you to borrow (hello, cashmere sweatshirt). Let the stress of DTR-ing commence.