Blind date: There’s no shame in being set up for a date by your friends or family. They just want the best for you, bud. Show your date that you just want the best for them (at least, in theory) by giving them a “promise ring." It'll give them tangible evidence to show their matchmaker at the end of the day. Plus, the Jonas Brothers are so over at this point that promise rings should be hip by now. (Ring from Urban Outfitters, $20)
In high school: She's your childhood sweetheart? That’s so sweet. Why not get her a digital photo frame so you can display all those years of extracurricular PDA in one convenient spot? Also, when the inevitable breakup occurs, it’s much more environmentally–friendly than making effigies out of your old photo albums. (Coby DP700WD 7-Inch Widescreen Digital Photo Frame, $30)
Hookup: It’s near impossible to give someone a present when you meet cute and fuck cute in the same hour. Plus, you met at Smoke's — no offense, but your whole romance reeks of desperation. So do the bare minimum: buy that lucky stranger a drink. And don’t forget a condom… you don’t want a belated Valentine’s Day present on November 14th. (Free at Penn Women's Center)
A week ago: This is really great timing, man. Not only did you snag a date for V–Day, but you guys are still in the honeymoon period. Nice. Celebrate your lust with some assless tights for her and some nude–colored tighty–whiteys for him. Stay classy, American Apparel. (Buy the Baby Rib Brief for $12 Sheer Luxe Cut-Out Pantyhose for $22 at American Apparel)
Feb Club: The birthstone for February is amethyst. Put that on your bling of choice, and suddenly meeting at Feb Club is not nearly as embarrassing. (Legit amethyst is probably pretty expensive, man.)
OCR: You were supposed to find a job. Instead you found love. That was the plot of Moulin Rouge!, too, except without the tuberculosis. Show your commitment to each other and your commitment to finance with a set of personalized business cards. (Buy 250 for $10 at Amazon.com)
Two months ago: Let's be honest; you're probably getting bored with the whole "dating" thing by now. Much like cramming for an essay the night before, you should probably just stick to traditional safe fare this Valentine’s Day before your plans become riddled with incoherency and Freudian slips. Frogro’s got the flowers, Wawa’s got the chocolates. You know what to do.
A couple years: You guys are practically married now. Just propose already, you crazy kids.