Pour some sugar on me, 1988.

Okay, guys. I need some help.

It seems that my 20 Year High School Reunion is in three days.

I knew it was coming up. It is. In three days.

This leaves me no time to lose those last few pounds, grow out my hair, or become a surgeon. If nothing else, I’m hoping (with your help, of course) that I can choose The Perfect Ensemble.

The reunion invitation states that dress is casual. However, I think I know better than that. These women (of which I am one! A Woman! I know!) haven’t seen each other in two decades. (Unless, unlike me, they attended the ten year reunion. Or, unlike me, perhaps they have the ability to maintain friendships from their teenage years. I’ve been in touch with no one. NO ONE. In other words, I’m walking into a room of strangers, and the only thing they might remember about me is that I tend to wear fake glasses and I fall down quite a bit.) Where was I? Oh, yeah. These women haven’t seen each other in two decades. You can’t tell me they’re going to be all, “Casual! Great! Honey, where are my cut-off shorts and my INXS t-shirt?”

This is where you come in. I’m about to give you three options. Please tell me which is most appropriate.


Here we have a knee-length denim skirt, a black t-shirt, and a short sleeved jacket thing that originally sold for $116, but I managed to score it for $11. Also, red patent Danskos. Because if I’m going to drink wine and fall down, I want everyone to notice my shiny feet. Not my Hanes Her Way underpants. (Note: Why, yes. I often stand like a flamingo when I’m sipping wine (or Pomegranate juice, in this case). Thanks for noticing!)

Next up? The dress that shows a bit of cleavage.


I purchased this dress for BlogHer, and it’s the most comfortable dress I’ve ever owned. Also, it requires absolutely no ironing! Polyester! With dots! And although I’m sporting black shoes, I think this might look a bit more dangerous with red shoes. Maybe. What do you think? (My grandma gave that stein to Jeff for Christmas many years ago. He keeps it in the freezer, and when he drinks from it, he speaks nothing but German. Obviously, I’m lying. BUT, cool stein. Cold stein, even. Klirrend!)

The final choice is a literal one. If you’re telling me that this event is truly casual, well, this is what you’re going to get.


Ratty jeans that may or may not be too tight, a black tank top that never really makes its way out of my drawer, my Ben Folds Five bucket hat, and my scratched up sunglasses. Also, a big stupid bag of frozen fish sticks, because I have to be holding something or else my hands will constantly be nervously shooting up to my face. (We’ll talk about that next week.)

So, anyway. Help.

Oh, yeah. Get this. Ira Glass is coming to town the night of my reunion. This is a huge conflict for me. If you know me at all, you know that I would drop just about anything to see Ira Glass. Let me just say this: If I have to wait 20 years to see Ira Glass again, I’m going to be So Angry with these people who waited 20 years to see me again. (I realize no one has really been waiting. If this thing wasn’t being held at an Elks Lodge, I’m positive I could do the Fly on the Wall game and no one would even recognize me!) If you live in St. Louis, please go see Ira Glass Saturday night. And while you’re there, pour a little of your drink to the floor and whisper something like, “For my misplaced homey, Fluid Pudding.”

I wonder if I should videotape the reunion so you can see how awkward I am in uncomfortable situations. Do you want me to? Because at this point, I’ll do just about anything for you. ‘ ‘ ‘text/javascript’>

99 thoughts on “Pour some sugar on me, 1988.”

  1. Delurking to throw in my two cents. These days when I get a “casual” invitation, I assume it means business casual. So I vote the dress as well, because it covers the dress up-down spectrum so nicely. And I would love to see it with red shoes. The other outfits are very cute, too.

  2. I am brand new to your blog, and came across it due to the “pour some sugar on me” tagline…great song. While I was here, I decided I would look at your outfits since my 20 year was last year…I say #2, however, my fashion style consists of jeans, t-shirts and Birks…I am just saying.

  3. Mutha Mae, all the way. ‘Zactly what she said.

    And the dress could be ok with red shoes, as long as they’re not those Danskos. I think I’d prefer black shoes, though. Pop in some color with accesories, if you like.

    Don’t get me wrong, the Dankos ARE cute (helloooooo red patent), but with jeans only. Or maybe brown cords. BUT THAT’S IT.

  4. Love the dress- it looks great. I think is shows you to a great advantage.

    IMHO- stick with black shoes, red shoes with the dress for this event might look “trying too hard” while as it was photographed it looks “effortlessly fantastic.”

  5. Delurking to say #2. It is totally classy and yet isn’t saying you were trying to show up every other woman in the room (the women who dressed dripping in diamonds at my 25th this year – No, I didn’t go but I saw the photos – were totally trying to do that), it fits your gorgeous figure, I agree you should stick with the black shoes and the MOST important point is that you said it is the most comfortable dress you’ve ever owned.

    What’s more important in an already uncomfortable situation than something you FEEL good in?

    That’s only if you really decide to go. I’d totally skip it for Ira Glass. There’s always the 25th. (I’d totally skip THAT to dog sit for a friend. Which I did, in fact…)

  6. Mutha Mae and Blackbird have told you all you need to know. I won’t even add a reason (except that you look just byootiful in that dress).

    Disappointed about Ira! Just (yesterday) told the husband all about your love affair with all things Glass. But Ira will return, and “the 20” will not!

  7. The dress for sure. It looks great on you and “casual” is over-rated. It isn’t too dressy, just right enough.

  8. I’m going w/the second option, minus the black heels and plus some cute red shoes. And accessories. And maybe a cardi to throw on if it gets chilly? To me, “casual” means “business casual”, so I wouldn’t wear denim anything. And those clogs? NOT with that dress. I’d always rather be slightly over- than under-dressed, kwim?

    Have fun at the reunion, and good on you for going! I’ve skipped both my 10th and 20th, and have no intentions of making my 30th, either. ;)

  9. I say option #1. It’s cute and fashion forward, so though you may FEEL awkward, you’ll LOOK relaxed, casual and together!

  10. I vote #3 but only if you bring the fish sticks. I really wanted to see Ira Glass Saturday but we are broke and I am sad. I will join you at his next local show.

  11. Agreed, #2 w/ red heels. I would love to see Ira Glass, but I already have plans to see Jim Gaffigan at the Fox. My best friend and I are so excited we keep talking about how “Jim Gaffigan will make us laugh again.” And my mom wanted to know when I’d seen Jim Gaff before, since we were seeing him again.

  12. I went to my 20 year last year. It was way better than the 10. Really enjoyed talking to people with whom I’d had little in common in h.s. (when I was kind of a prissy nerd) and finding that we have lots in common now (books, kids, wine, etc.)
    I vote for #2 (really adorable on you), or #1 with a black skirt (fun and hip – but not too out there) – depending on whether you want to blend, or strut it a little more. Also – looks to me like WW did you right – I don’t see any weight that needs losing.
    If you go – have a great time! I didn’t regret it. Ira Glass will come again in six months- next reunion is 10 years away.

  13. I went to my 10th and 20th reunions and had a ball at both. Not because I as at all popular either. For a writer it’s like someone threw 6 months of research in a room and gave it to you. From that experience I say that dress + red non-Danskos = reunion GOLD! If the tan issue gives you pause bring a wrap or sweater.

    Have fun!

  14. Both 1 and 2 look fabulous, but since you mention that you’ll be feeling awkward all evening, I think you’ll feel altogether more comfortable in #1.

  15. I own that dress you wore to BlogHer, in a (cough) larger size. It’s totally comfortable, and won’t do anything unexpected.

  16. That sassy little number in the first pic is fantastic and I would love to see you add the accessory of the fish sticks, please? It would totally complement the red shiny shoes.

    Have fun!

    Ira is coming here in November. Want to just come visit me and ogle him together?

  17. I really like the cleavage one (not in a weird way), and I’m such a dork I’d probably end up wearing red clogs with it, so don’t listen to me. Since you asked (I think), if it were me I’d totally go see Ira Glass instead of going to the reunion. But that’s just me. I had my 20-year reunion this summer and apart from connecting with one long-lost friend (which in reality could have been accomplished by picking up the phone), I really could have skipped the whole shebang and saved tons of money (dress, shoes, hair, nails, serious undergarments, makeup, therapy) and stress for something else. But have fun!

  18. I’d be more likely to wear 1, but I say go for 2 simply because you look fantastic in it. And I have to agree, unless you can read your keynote blog at the reunion, (that would get things going) go see Ira Glass!

  19. Fishfingers in my culture, people. Fish FINGERS. Thank you.

    Otherwise, I can’t see the pics, but going on the description alone, I’d have to say #2. Reunion will be blogging gold. I await.

  20. i have a ticket for ira,but can’t go since i have a child attached to my breast. you have to pay for ‘everyone’ at the pageant. ridicule!!

    i like #1 since it seems more you. the dress is cute, though, so i won’ t be mad if you wear it.

  21. What 10 lbs? I like both 1 & 2 so wear what makes you feel comfy – cause they both look good. Definitely bring the fish sticks.

  22. Seriously, you don’t have 10 pounds to lose, you gorgeous woman. I like the dress the best. With a pair of red heels, if you have them.

  23. The first concert I ever went to was Def Leppard’s Hysteria tour…in Casper Wyoming. I remember the smug superiority I felt when, afterward, I was at a dance and watched a girl singing along with the song, crooning, “my love for sure!” instead of the accurate “one lump or two?”

    I really think I pitied her. Candidly…I think I still do.

  24. All of the outfits were boring, except for the jeans. You look older than you probably are. Find you a smoking hot outfit that everyone wished they had on. Try a younger outfit. something sassy.

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