The Clueless Single Guy’s Guide to Valentine’s Day

Most women love Valentine’s Day with a fervor equal to the level at which men hate it.

But if single men were just a bit wiser to the ways of the holiday, they might find it less daunting and a lot more exciting to look forward to. These five simple questions will help guide you through this potentially treacherous holiday.

1. Surprise … or not? Some women just love surprises. Others, not so much. For example, if you surprise your date with a weekend away at a luxury resort, you may think you’re giving her an amazing gift. She, however, might appreciate the gift of a little forewarning so she can make sure she has a suit that fits (and a few days of crash dieting) as well as a bikini wax. The exception? Popping the question. Should you choose to use this day to propose, just be sure that you’re not the one surprised. Remember, you’re shooting for screams, tears, and a resounding, “yes,” not a long, awkward pause.
2. Chocolate, flowers, or both? In most cases, one might think “both” would probably be the best answer. However it is here where it’s important that you know your girlfriend … well. Is she the type to respond to your chocolate generosity with, “What? Are you trying
   to sabotage my diet?” If so, stick with flowers. But your worries aren’t over yet. There are flower types … and colors. Pink roses? Red? And if you think you haven’t been dating long enough to get her roses, you’d better reconsider before substituting carnations. That is, if you ever want to see her again.
3. Casual … or dress-up? Most women will love the opportunity to put on a dress and heels. So, unless you’re absolutely sure your girl would prefer a casual night out, opt for a dressier dinner. But, that also means you have to be up for the occasion, too. The clueless guy won’t understand how showing up in jeans ruins her outfit. You don’t have to understand. Just know that it’s true, and dress appropriately. Besides, seeing you in a suit and tie or at least a dress shirt is as effective an aphrodisiac as a full order of oysters … and cheaper, too.
4. When to ask? This is a toughie. And a lot depends on how long you’ve been dating. If you’ve been together long enough that a Valentine’s Day date is expected, then you can wait. But, don’t wait too long. You see, part of the fun for her is the anticipation. She wants to be able to tell her friends what you’re both doing long in advance. And she may want to prepare with a new outfit, too. If you haven’t been dating too long, don’t ask too soon. It could scare her … or you … away. But, if you really like her, make sure your contact with her stays steady up until the day you do ask. Somewhere in the middle? Then your date request is somewhere in the middle, too. Wait too long, and you could piss her off irreparably. Ask too soon, and it could signal something more serious than you’re prepared to, well, signal.
5. Sexy gift … or simply friendly? Again, this answer depends on how long you’ve been dating … on both ends of the spectrum. Give a sexy gift if you’ve been dating long enough to be able to talk (and laugh) openly about the sexual aspects of your relationship. New relationship? It’s probably a good idea to stick with #2. Valentine’s Day is special enough. Finally, if you have been dating so long that you’re spending Valentine’s Day with your girlfriend, a pizza, and a movie on the couch (and you’re both okay with it), then be careful. Sexy is okay, unless it comes with a note including any of the following phrases, “just a reminder,” “you owe me,” “I’ve forgotten what it’s like,” or “it’s been so long.”

Remember, you’re just five questions away from a happier, stress-free Valentine’s Day!