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Tag Archives: Valentine’s Day

I don't need to flirt, I will seduce you with my awkwardness.I’m filling in to teach a class for a sick friend + have a giant pile of work to do, and there’s probably no way we’re topping this as a Valentine’s Day post, so, here you go. [<3]

Consider this an open thread to share stories of ways people (friends, family, partners, teachers, coworkers, anyone!) have shown you that they’re on Team You.

Every Kiss Begins With Kay

I grudgingly bought you this ugly necklace because commercials told me I was supposed to. Now you have to wear it and pretend to like it for the rest of time.

Hello, it’s time for the day where if you are single you feel pressure to be in a couple and if you are in a couple you feel free to do something “special” and romantic that will satisfy the other person’s secret unspoken hopes and expectations for what Valentine’s Day should be like.  The potential for Overthinking It + Trying Too Hard = CAPTAIN AWKWARD GOLD.

First, if you’d like to give Captain Awkward a valentine, you can go vote for my guest post (The Man Who Would Not Break Eye Contact) at Sexy Typewriter.  Or vote for one of the other posts – it was a carnival of hilarity!

Second, a reader writes:

Hey Captain Awkward, I’ve been seeing this girl for about three weeks and I kind of blanked on Valentine’s Day, but now it’s here, and we’re supposed to hang out later, and I don’t know if she has expectations that we should do something special.  I’m a college student and don’t have a lot of money to go to fancy restaurants, and everything’s super-expensive tonight anyway.  Any advice?

This kind of question is what sends otherwise brave men to the terrifying pink and red aisle of the pharmacy or grocery store.  Resist!  If you like this girl and things are meant to be with her, it will be okay for you to just say “Hi, I kind of blanked on the whole Valentine’s Day thing, but I do really like you and am really glad we got to hang out today.”   Then you should just do whatever you did those other times that you hung out over the past three weeks, maybe with some extra kissing thrown in.  If you really want to go over the top, a couple weeks from now, get her flowers (NOT RED ROSES, THEY ARE PLAYED OUT – think tulips or irises or lilies) for no reason other than “I’m really happy with how things are going and I thought you might like these.”

MehIf you’re the guy who blanks on Valentine’s Day, but she is a girl who expects les fleurs et le chocolat and dinner at a place with prix fixe and fondue and gets disappointed when they don’t appear because you didn’t magically read her mind or save up hundreds of dollars to celebrate a “special” day in exactly the way that everyone else celebrates that day, every single holiday is going to be a study in disappointment.

A good guiding principle:  If it’s not fun for you and doesn’t come naturally, don’t do it on Valentine’s Day or any other day.

Let me also say:  Except in the minds of all mainstream marketing and media outlets everywhere, Valentine’s Day is not some holiday where men “prove” their devotion by buying crap for ladies.  However, the questioner is a man thinking about whether to do something special for a lady, and I’m going with his flow.  Hopefully his lady also has some butterflies in her stomach and will be doing something nice for him tonight.

I think the best gifts are ones that showed that you pay attention.  I read a lot of student screenplays where the writer is at pains to represent romance visually, so they are full of generic symbols like flowers and heart-shaped boxes of chocolate and stuffed teddy bears holding hearts and engagement rings (that are thrown in the lake when the relationship sours, which seems expensive and wasteful to me).  Probably the most romantic Valentine’s gift I’ve ever received was an external hard drive that I still use to this day for video editing.  It was a new relationship and the person (Intern Paul, if you must know) showed me that he understood what I was about.

In the past, when a boyfriend sent me a big bunch of roses at work, it felt a) like he was territorially peeing on me by displaying to everyone that I was ‘taken,’ and b) like everyone in the office was way too interested in the whole thing.  I was in a special Club now, the Club of Women Who Get Roses on Valentine’s Day, and who are somehow Special and Chosen, and women who were not in The Club were looking at my flowers and feeling bad about themselves or about me, like “Wait, I’m single and she’s not?  But she is so fat and crazy and weird!”  I don’t know, maybe for some women it’s really important to be in The Club, and what men do by sending Valentine’s Day flowers to work is give them the gift of being in The Club.  Having been in The Club, I’ll take half a terabyte of video storage from a dude who knows my deep abiding love of Final Cut Pro.

If you did leave things until the last minute, and you do feel like you want to make some gesture, here are a few inexpensive catch-all suggestions.

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