If It's Your First Date
Wow. You've planned your first date on Valentine's Day. That is extremely bold of you. Anyone who agrees to a VDay first date has a pretty solid crush, so you have that going for you. However, you are entering into territory with high stakes so don't expect too much to happen or you'll likely be let down.
To Give Him: If he's cute? 15 minutes of hardcore kissing. Valentine's Day is not—repeat not—the day to go home with a guy on the first date, if that's something you typically are into. Also, don't get him a gift, unless it's something very insignificant but sweet.
To Get from Him: Flowers. He best be packing flowers if he's taking you out on Valentine's Day. If you're gonna do it guy, do it right.
If You're a Few Dates In
Things are going well, but you're still getting to know each other. Likely neither of you expects a huge sweeping gesture this early on (if you do, you need to check your expectations). In fact, neither of you are planning to make a date to go out on Valentine's Day.
To Give Him: You can send him a silly or fun photo of yourself by text. Say something like, "Out with the girls." It at least reassures him you're not on a super romantic date with another guy.
To Get from Him: He might try to avoid communication on this day like the plague. Or he might text something like, "Where do you come down on this whole Valentine's Day thing?" to gauge the temperature. If he was super into it himself you would already have plans on the books.
If You've Been Dating a Month
You've seen his place. Met his cat. Spent the night perhaps. Things are going well, all things considered. An actual gift is not off the table. If Valentine's Day is important to you, my advice is to let your guy know well in advance, so he doesn't disappoint you either way. If he shows up at your place with a horse and carriage waiting outside and you're in your pajamas it might get awkward.
To Give Him: If you're sleeping together? No need to break the bank, but wearing a matching bra and underwear set is a nice touch. Doesn't hurt to add a bow.
To Get from Him: He might do the traditional flowers or chocolates, but ideally he will take the opportunity to buy a small but more thoughtful gift such as the DVD of that childhood movie you mentioned you loved. This won't be a big gesture, but a token of affection. And no, don't expect the horse and carriage. I was joking. If he does that, he's very serious about you.
If You've Been Dating Three Months
Things are getting real. Likely you've had "the talk" and are exclusive. If you are on the same page about celebrating this holiday this may be the first time you have a chance to offer significant gifts to each other. At the same time, it's Valentine's Day, not his birthday. So it's not the time to necessarily go too big, but you can still be thoughtful.
To Give Him: Balance the attitude of "this is going somewhere" with "this is a romantic holiday" by doing two gifts. The first is for him: Something he has mentioned in passing that he wanted to try. Don't break the bank. It can be his first set of cuff links, for example, or an intro yoga class. One gent I know pointed out that a bottle of tequila would also work. The second gift is for you both: This is a good opportunity to introduce sexy lingerie into the relationship.
To Get from Him: He might have squirreled away a thoughtful gift or two in the previous month. Similarly, he didn't shell out tons of money, but it might be something sweet reflecting on the time you have shared, or tickets for a show you guys have talked about seeing together.
If You've Been Dating Six Months
You guys are the real deal. Assuming things are strong, you have talked at some point along the way about how you feel about Valentine's Day. Either you take it seriously or not, but what you decide here will set the precedent for the rest of your relationship. If you have a frank talk and say, "Not for us," cool. But if you decide this is a chance to celebrate love, kick it up a notch.
To Give Him: Extra special sex. At this point you guys may have fallen into a certain groove in the bedroom and this is a chance to shake that up a bit. Alternatively, a meaningful gift that the two of you can share: couples massage or tickets to a football game.
To Get from Him: Flowers should be a given. Also, a heart-felt card. But he should have lined up dinner reservation weeks in advance and planned a nice night out with you. A thoughtful present might be a part of his plans, but the night out together is the main gift.
If You've Been Dating a Year
Congratulations. You guys are probably making big enough strides in your relationship to the extent that Valentine's Day is talked about more like, "What should we do Thursday" than "OMG what's our dynamic on this weird holiday?" It's likely not even your first Valentine's Day, but it might be the first one when you give each other gifts.
To Give Him: This is a nice opportunity to surprise him with that "I would love it but not gonna splurge" item he's been eyeing.
To Get from Him: He should reciprocate with a thoughtful gift for you (and by thoughtful I mean gifting you that bracelet or clutch you've been dropping hints about). Or he might buy some lingerie for you to wear. After all, we are pretty simple, us men.