Reader question #48: A cool, nice guy asked me to prom, but now our awkward silences are making me worry.

Dear Captain Awkward,

So my prom is coming up (it’s at the end of May) and I was asked to prom by this guy. He’s been in some of my classes and I’m really excited that we’re going together. We hang out, but our conversations always turn out, well, awkward (as in lots of awkward silences). I think this guy is pretty cool and I’d like to go to prom with him, but I’m just not good at having conversations. This isn’t just a problem with this guy, it’s kind of a chronic issue. I just don’t know how to have a conversation or just “hang out” with people (the exception is close friends, but this guy was more of an acquaintance until a week ago). I usually hang out with a group of people, but that doesn’t exactly work with a date. Can you give me some tips to make this prom, and all of my conversations, less awkward?

Awkward Prom Date

Prom is fucking weird.  Dating is fucking weird.  I think that formal dances like prom were supposed to maybe prepare you for adult dating?  Maybe that was true back in the day where you sort of met your future husband a couple times at formal dances before you became his property (close your eyes and think of England!)  Now proms seem more like 1) excuses for makeover montages in teen movies and 2) preparation for dating reality shows where everyone goes on very stilted, awkward manufactured “dates” and then stands around crying in prom dresses over whether some bland dude is going to give them a rose.

And now, a poll. Which is worse?

This collection of bad prom dresses from the cast of the Bachelor, present day?


This collection of bad cocktail dresses I wore to school dances, circa 1989?

Let your eyes recover from that for a moment….

Okay!  Your question!  While you and your date have temporarily entered a dimension I’ll shorthand as “A Michael Cera  movie with extra stilted pauses” the good news is that actual proms are not like movie proms, and that you’ll probably have way more fun if you and your date go with a bunch of friends, so it will be like hanging out with people you like except everyone is more dressed up and one of them is designated Your Date.  There is safety in numbers, and you will remove the pressure to magically connect romantically with this dude.

I also think you can use the weirdness of the occasion in your favor.  You are two normal high school students who are undergoing a very weird ritual together.  Fortunately you have a script for the night – one of you will pick the other one up, and then there will be posing for photos with parents while they coo over how grown up you are (weird!), corsages (weird!), promenading around while trying to walk in dress shoes (weird!), seeing everyone dressed up (weird!), seeing your teachers in formal wear (really weird!), trying to slow dance to whatever bad songs the wedding band hired for the occasion will try to cover…(and if you want to see something weird, go to that video and see the message the guy who uploaded it posted under it), whatever gross rigamarole your school goes through to elect prom king and queen (weird).  The collective weirdness of the night might make talking to each other seem really normal by comparison and you will have bonded in the face of adversity.

So for prom:  Try to band together with friends and go as a group.  Don’t force it, watch the drinking, don’t feel like you have to have a romantic connection, definitely do not feel like you have to have sex, and whatever you do, don’t wear floral print because your moms will keep and display those photos forever.

For conversations in general, eh, my dad gave me advice for dealing with big networking events with strangers by saying “Everyone feels weird at those things, so pick out someone who is standing alone, go over to them, introduce yourself, and think about how by being friendly you are making it less weird for one person at a time.”  It’s okay to be a small group person, or a one-on-one person, and it’s okay to be quiet as long as it’s a “I’m listening intently to the other person” silence and not the silence of “Oh god, I am so self-conscious right now I can’t even hear what the other person is saying so I just try to nod and smile” silence.  (The good news?  No one can tell the difference most of the time.  Bad news – You might find yourself nodding and smiling at the wrong time and eventually get called out on it).  Everyone is a self-conscious awkward freak inside, so you can maybe let go of some of your own self-consciousness by doing what you can to be kind and attentive to others.

And hey, the other good news is that I talked to my prom date on the phone the other day and we’re still friends after…eep…21 years.

Readers? Got any good prom stories or social anxiety advice?

20 thoughts on “Reader question #48: A cool, nice guy asked me to prom, but now our awkward silences are making me worry.

  1. My prom date was a guy I knew from music lessons who went to a different school. I could tell he really wasn’t into me… I just didn’t realize exactly how not into me he was until I heard many years later that he’d been fired from his teaching job for molesting the young boys in his class. Kinda I didn’t see him again after prom!

  2. I was “fortunate” enough to go to 2 proms. One my Sophomore year with boy from next town over and my Sr Prom. Sophomore year, yikes. My date was someone who prided himself on being as much like “Silent Bob” as he could possibly be, down to the no talking and undying love for Star Wars. (not insulting the “geeks” of the world, I’m one too!) I later found out that he was incredibly shy and liked me. Nice guy, but it wasn’t going to happen. To make our incredibly long uncomfortable silences slightly more bearable, there was a running gag about long awkward pauses that just wasn’t funny. My Sr. Year prom, as close to a typical story as you get. I went with my boyfriend, hung out with my closest friends, and spent the weekend at the beach with friends etc etc.

  3. This happened to me! Only things were even more awkward because when the cool, nice, awkward guy asked me to go to the prom with him, for some reason, I blurted out, “I’ll go with you if you tattoo my name to your chest! Haha! Kidding!” He looked really scared after that, and our encounters were awkward and silent for a couple of weeks.

    But then we went to the prom and I wore a stick-on skull tattoo on my leg and we did silly dances and we’re still dating 10 years later.

  4. My prom date (who professed to be in love with me at the time and subsequently turned out to be gay) and I got lost on the drive from dinner to the river boat on which our prom was being held. We had to chase the boat down the river and catch it when it got to a boat lock. As we climbed aboard, we heard the DJ announce, “Let’s hear it for B and E, who just got here!” The rest was pretty standard, including 4 AM diner pancakes and someone getting in trouble with someone else’s mom for being drunk. Ah prom…

    1. The theater/chorus kid and the gay prom date? NO. I DON’T BELIEVE YOU. 😉

      1. B may have been fooling himself, but he did not fool me. Need I even mention that he also asked me out on a date to see the national touring production of Beauty and the Beast?

  5. Advice for making small talk with anyone:

    Always have three interesting out-of-nowhere stories on you. Something science, something celebrity, something history.

    Just look up a science blog, or a history blog, or a music blog, whatever, and if you have gotten past your hellos and the awkward begins (noting that some awkward is good to get used to), go ahead and say Oh! I was reading this super interesting thing about… and explain the phenomenon or the recently discovered civilization or the famous person who also has a doctorate or whatever. If he has any social grace at all, it will remind him of something HE read, or he’ll react to what you tell him.

    By having three “safe” stories tucked in your head, you have 3 awkward moments saved. I have to go to a lot of conferences and this method has saved me dozens of times from serious boredom and awkward moments.

    1. As someone who’s critically Small-Talk Impaired, this is some of the most useful advice I’ve heard in a while. Usually, whenever awkward silences come up, my mind jumps straight to interesting animal mating habits and has trouble going anywhere else. Awesome in some situations, not so much in others.

      Anyway, thanks!

  6. I can so totally relate! I used to be the queen of awkwardness, and ended up having discussions with both my mum and my psychologist about how to actually talk to other people.

    Best advice I ever got: Most people like to talk about themselves, so ask them questions. Preferably something you’re genuinely interested in, but stuff like what hobbies they have, what they like to do/watch/read/listen to, future plans (further education, summer holidays, jobs, etc), and family (do you have any siblings? Pets? What do your parents do?) can all work. Don’t be afraid to be a little nosy.

    Something I learned later was to just start talking to strangers as if I’d already met them before. Choose the same conversation topics that you’d use with your friends: recent events, big news stories, mutual acquaintances, what are they doing this week/weekend, topics you know they’re interested in, classes you both have, and so on. “How are you?” may be a good one to start with. (Where I live it’s a culturally automatic conversation opener, and people may either say ‘good’, or actually elaborate.)

    One last thing, because this is getting long: Don’t be afraid of silences! Sometimes you just can’t think of anything to say, and that’s all right.

  7. ALSO! It’s very important to have some planned ways to get a break:

    1) I see my (favorite math teacher/person I owe $4 to/nemesis) over there, and have to go (say goodbye/pay her off/hide).
    2) Excuse me for a moment while I run to (the ladies room/the bar/the smoking area).

    The trick is: do NOT hide in the ladies room all night, and don’t ditch him 15 minutes after you arrive and have pictures taken. Both of those routes are unfair to the date AND to you!

  8. One time I went to a concert with a guy I used to know real well but hadn’t seen in years. At the end of the night I told him how great it was that we could have those companionable silences that we didn’t feel forced to fill. What a hallmark of our deep friendship, etc. And he sputtered, “Those felt companionable to you? I thought they were awkward! I’ve been in agony trying to come up with something to say!” Go figure.

    Love the advice given so far about conversations and chatting. That’s a skill that will be useful your WHOLE life, and something that’s great to start developing now and keep working on.

    One of the best conversation-starters I ever heard a guy use (as an adult) was “tell me about your high school prom” (which he then followed up with a gripping tale of his own prom disaster; it was fabulous) but that won’t work for you yet, obviously.

    It’s definitely good to have some ideas in your figurative pocket. I can’t tell you how often magazines have saved me by keeping me up on the latest pop culture stuff. Entertainment Weekly for the win! And yes, people love to feel like you’re interested in them.

  9. Also, if you do do the “talk about other person’s interests and hobbies” thing and you don’t have things in common there, see if you have a funny story about that thing which illustrates why you do not do it. Example, I was making small talk at work with this dude I was helping train, and he was really into skateboarding. I am the least athletic person ever, so I told him about my many hilarious attempts to do athletic things like ice skating and roller skating/blading, that always end with me falling down at least 3 times a minute. This also allows your acquaintance to tell a slightly embarassing but funny story in return. In general, it’s kind of good to have funny stories you can pull out of your life. I usually go with what was funny to my friends when I told them (and is apppropriate to the occasion).

  10. My crucial piece of advice: if you do not normally wear makeup, do not wear makeup for the prom. It’ll be hard to do it right. I was not familiar with cosmetic techniques and didn’t own any (or have money to run out and buy), so I asked my girlfriend to do it for me–because she did it on herself so well. But it was really not suitable, and I feel horrible every time I think of what I looked like that night!

    My awkward prom issue was that the guy who asked me was just a casual classmate–we admired each others’ sense of humor, but would never have considered dating–and I was like, a 10th choice. But he insisted on conducting the evening like it was a big prom date, so we ate at a fancy restaurant and went to a romantic spot at the end of the evening…totally not me, and made me feel very consciously like a stand-in for someone else. Then he complained to everyone the next day that I talked too much at dinner and made us late to the prom itself…whatever dude. A disaster all-round!

    1. If you don’t normally wear makeup, it can be fun wearing makeup to prom since the contrast will be quite striking.

      But yes, don’t get a friend to do it– they will probably do your makeup like they do their own, and this might be all right, or it might be utterly horrifying. Go to a spa or cosmetic studio like Merle Norman or whatever and have it done professionally (if you can afford it, of course).

  11. Thank you (all of you) for the advice! My prom was so much fun and not awkward 😀

  12. So I just asked a boy in one of my classes to come to prom with me, and I think he’s really funny but when I talk to him about prom it’s always really weird. I think he wants to go with me, but I don’t know what to do before hand because I think making him hang out with my friends would be weird and his friends are not even going. Also, this guy is really hard to hold a conversation with because he’s just a socially awkward person. How can I improve this situation?

    1. You can’t make someone less socially awkward, but you can suggest a casual hanging out – to the movies? To grab a bite? – to get to know each other better, which means he might relax a bit and be easier to talk to. Have fun!

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