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Dear Captain,

A year ago I (she, 26) made a male friend (25) over OkCupid. We were both just looking for new people to hang out with, I was lonely after  moving to a new city, and also happy to make a male friend because all my other friends are female. We started hanging out pretty regularly, just watching movies at home or going out for coffee or food.

Fast-forward a year, I invited him to my birthday party. At midnight  everyone gave me their gift, but he said that he would only give me his  when he leaves, so he doesn’t have to see me open it. He had done the  same at Christmas, so I wasn’t surprised, but imagine my shock when this  time, instead of a cute plushie, I opened the wrapping to see…a purple dildo. I was so shocked. The card he gave me explained how it was supposed to fit all the things on the list of “things I like” that I mailed to all my friends who weren’t sure what to gift me and I guess it was sort of a clever and funny play of words?

My friends laughed hysterically for like an hour, and I laughed with them, but the more I thought about it, the more disappointed I was. I have, I guess you could say a *thing* with presents, which is that I really really hate things I cannot use. I grew up poor and I like owning things of value and he knew that. I mean, that’s the whole reason of why
I sent that list around. But instead of respecting my wishes (and really, it’s not like they were outlandish, I wrote “stuff for my balcony” on that list so he could’ve literally just gotten me a plant), he chose to make a joke that *he* thought would be funny. Maybe I’m
being selfish, but to me, that’s an insult. It’s not even about the fact that it’s a sex toy (he knows I’m asexual), I wasn’t mad about that. I was mad that he didn’t think about what *I* would want.

I then told him that while it was funny for a while, I would prefer him to take it back and just give me the money. He refused, telling me how “disappointed” he is that I didn’t like his “troll gift” (literal quote), thus making everything about himself again.

Since then I’ve been unable to get myself to like him again. It’s like the floodgates have broken and I’ve started noticing other stuff that has been bothering me for a while but that I’ve overlooked – him never offering to do the dishes when we eat at my place, leaving behind a huge pile of trash when we get takeout, never checking in over Whatsapp how I’m doing, almost never being the one to set up the meeting place and
time for our meetings, never talking about #deep stuff and just joking around when I try…

He’s not a bad person, I know that if I tell him what bothers me, he will probably try to work at it. But why should I be the one to teach him basic manners? I’m not sure I want to take on that emotional labor. I can’t stop comparing him to my female friends, and I work a lot so I have to carefully choose the relationships I want to invest time in. Am
I really going to end a friendship over a dildo? On the other hand, were we really such good friends in the first place, or was I just lonely? Will I like him again if some time passes? Please help?

–Disappointed Birthday Girl

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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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