1.) Book the dinner reservations immediately. Things fill up fast and many restaurants have a set menu for the night. Avoid those and get a good table somewhere nice, this will allow you to
2.) Let her dress up. Most women absolutely love dressing up. They love wearing a nice dress, they love taking photos while dressed up, and they just feel so much more confident and sexy. This wont fly at your local greasy spoon, so pick a restaurant accordingly where this kind of apparel is normal.
3.) Most women HATE being unsure about what sort of dress is expected on date nights, as they both want to fit in with the environment and be prepared. Be very cleareven if its a surprise (not usually recommended unless its something truly memorable and extraordinary)so she feels very confident going into picking out her outfit.
4.) That also means you have to dress up. If youre not a typical suit guy and dont feel bulletproof in the one hanging up in your closet, run it over to a tailor ASAP, it wont cost an arm and a leg. Shell notice how much better it fits and its also something that youll be able to use again and again post V-Day. If the environment calls, you can also roll with a shirt/tie/sweater combo, like Mr. John Legend pulls off nicely above, assuming you look as cool as he does in the photo.
5.) If the restaurant lets you bring your own wine for a corkage fee, bringing the bottle youve been saving for a special occasion is a nice touch.
6.) If you want to add to the specialness this year, try doing a little staycation over the Valentines Day weekend. Pick a nice resort to stay at within a two hour distance of your home. No hustle and bustle with hoping on a plane, just a one (or ideally two or three) night stay somewhere really cool.
7.) Get flowers delivered. If you bring a big bouquet of flowers to her when picking her up the day/night of, she has to deal with the trouble of finding the right vase, cutting the stems, and all that other nonsense. Your best bet is to send them to her office the day before. Shell feel left out if other girls in the office have flowers and she doesnt, plus shell get to look at them a lot longer.
8.) You dont need to buy her affection with some crazy expensive present. Just get her something thats in a comfortable price range for you that MEANS something. We highly recommended these.
9.) A card is also clutch. Even if you havent said those three little words, writing something heartfelt and charming will leave her incredibly happy.
10.) If youre comfortable enough in the romantic aspect of your relationship, skip the cheesy and cheap lingerie that will make her feel like a prostitute. We recommended something from La Perla. Classy, quality, but still dangerously sexy.
11.) Pick up a disposable film camera for a few bucks and snap a few shots of you two while out and about. The not knowing what they look like right away factor is a lot of fun, it will force you to take a whole bunch of photos you might not normally take, and almost every person looks better on film than they do digital.
12.) Enjoy it. Be comfortable, confident, and fun. If youre having a good time, shell be having a good time.