Whether Valentine’s Day has you cheering, groaning, or feeling completely apathetic, there are pluses and minuses on every point of the spectrum. Here are my picks for the top 3 worst and best things about Cupid’s day of glory. Let’s get the BAD out first:
1. This special occasion makes the process of scheduling a date, coffee, or time to get to know someone you are potentially interested in incredibly awkward. Do you bring up Valentine’s Day? Do you not? What if you’ve been together just a few weeks? What if you have been together longer but aren’t sure where you want things to go?

No matter what you say or do, women will (not surprisingly) read into everything. So take time to think about this. If you want the other person to know they are special to you, there is nothing wrong with playing up the evening, mentioning it, or buying something nice, as long as these things are your date’s style. (Hint: if she’s easily delighted by small gestures or tokens, all of the above should go over well. If she is a minimalist and isn’t into gifts or holidays, play it cool – send her a funny Valentine’s Day text and gauge her response/interest first). Whether you like the person or not, there are enough things to worry about without this anxiety amplifier. Sigh.
2. Flowers are stupidly expensive. It doesn’t matter why you are buying them. Maybe they are for your friend’s housewarming party, a niece’s dance recital, decorations to brighten your living room, basically anything aside from showering a loved one with Valentine’s day greetings. Chances are, you are going to pay a bucket-load more for them than you would on any other day. So either settle for a non-flowering potted plant or be ready to shell out some major cash for events you wished were on any other day of the year.
3. For a minimum of one weekend and potentially more, scheduling plans with friends is as hopeless as it gets. Some couples celebrate Cupid’s Day the weekend before, some the weekend after, and others on whatever day of the week the “holiday” actually falls. If you have a birthday mid-February, good luck. Chances are the day you choose won’t work for everyone, potentially your dearest friends. Do you celebrate without them, or wait until two weeks after your birthday to make a toast? If you have a significant other, another event might take precedence. Maybe you have to go to the birthday party for your weird aunt so you don’t infuriate your family. I feel for you.
Thankfully, there are also things you can look forward to during the season of love. For starters:
1. People are going to look particularly nice leading up to and on Valentine’s Day. Women tend to get their nails and hair done, men (who are smart) don their dressier gear – and guess what? They turn heads, and deservedly so. Who doesn’t like a man decked out or in uniform?
Who can’t appreciate a woman who went the extra mile to look her best?
Think of all the eyeballing that goes on when you hit the first day of summer. That same flash of brilliance people bring to the table on the 14th is an instant mood booster. So get your share by dressing up, keeping your eyes open, and basking in the compliments from people who know you or admire from afar.
2. Chocolate, chocolate everywhere! This aphrodisiac is in practically every location you can find, and often for free. Things that don’t normally come in chocolate flavors often do at this time of the year. (Valentine’s Day flavored tea?? I don’t know exactly what this means but it sounds delicious!) Keep your eyes open for free chocolate samples of every variety.

3. Date auctions – If you are looking for a fun night out, this is the way to go. And not just for those who are trying to win over someone on the auction block: from the cocktail hour and appetizers to seeing how high the bidding goes, these are truly entertaining affairs. They even spur some creative antics that you won’t want to miss. If in doubt, just take a look at these moments from the Sip with Socialites fundraiser last month.
 
A huge bonus is that that money raised goes to wonderful charities, such as the Social DC Public Relations fundraiser for Multiple Sclerosis. The auction featured ABC’s The Bachelor/The Bachelorette star Chris Bukowski and America’s Miss DC Sarah Hillware.
“Date auctions are always a fun way to fund raise ” said Hillware, whose date called in from Philadelphia to place his winning bid. “It even gives me an excuse to dress up!”
If you haven’t been to one yet, you’re in luck – Sip with Socialites has one more set for Wednesday, February 13. Whether you’re single, taken, or somewhere in between, you’re guaranteed a good laugh.
So whether you love Valentine’s Day or hate it, here’s a tip for everyone: please don’t get anyone this – unless they are on your bad list, in which case it may be a good use of your frustration.
HAPPY VALENTINE’S DAY!
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Tags: Listen to anything a pretty DC woman tells you
