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The Second City: U2 returning to Chicago is the new Obama Farewell Address

So maybe you didn't get a seat to that other big event last week, but for all of you who missed out on witnessing President Obama's farewell address in person, get ready for the next historically significant affair rolling into town: Bono, Drumming Bono, Bass Bono and The Edge Bono will all be...

The Second City Network

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Ask Anna: Dating & Sex

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  • Ask Anna: Is confidence really key?

    Ask Anna: Is confidence really key?

    I've been faking it but haven't made it yet. People keep telling me that women like confidence, but confidence in myself as a dating partner is hard to find. All of my experiences tell me I'm not the most physically attractive guy. My personality has gotten me a good amount of female friends, but...

  • To snoop or not to snoop?

    To snoop or not to snoop?

    I read recently about the new iPhone feature being able to accept up to five fingerprints to allow phone access. This has started a curious debate with my boyfriend about whether he should be one of those prints. The thought that he could have unrestricted access to my phone is abhorrent to me,...

  • Can I be friends with my daughter’s father?

    Can I be friends with my daughter’s father?

    Dear Anna, My ex and I have been separated since our daughter was 9 months old (she’s almost 2 now), and we still keep in contact, of course for our child, but also for non-child-related reasons. By the time I moved out of his house, he was already talking to a new girl, now his girlfriend, who...

Threesome

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More opinion

  • Threesome Advice Panel: Should I tell my Tinder match how tall I am?

    Threesome Advice Panel: Should I tell my Tinder match how tall I am?

    I've been talking with this girl [on Tinder] for about two weeks now. My first and only Tinder date this past summer wasn't that great, her photos were old and very misleading, which made things awkward for me as the attraction wasn't there for me. I'm a short guy, about 5’5”. She's 5’8”. Now should...

  • Ask Anna: We broke up and I need you to tell me it'll be OK

    Ask Anna: We broke up and I need you to tell me it'll be OK

    I had been with my (now) ex-girlfriend for two years, and this year has taken a toll on us. She lost a parent and then we broke up for two months and got back together, but it was rocky. We broke up again the day before Christmas. I love her, but I doubt we will get back together. I need some advice....

  • Threesome Advice Panel: My boyfriend and I might have broken up. How do I fix it?

    Threesome Advice Panel: My boyfriend and I might have broken up. How do I fix it?

    So my boyfriend of almost two years broke up with me two nights ago, and he says we won’t get back together because we broke up before and things went back to the way they were. But I’m trying to explain to him that we haven’t taken a couple of days apart, and now that we have, I’ve had time to...

  • The Second City: A year-end wrap-up from everyone's nemesis, the year 2016

    The Second City: A year-end wrap-up from everyone's nemesis, the year 2016

    Do you have any idea how hard it is to be a year? There’s a reason the job only lasts 365 days (or, for overachievers like me, 366). It’s tough to be compared with all the great ones that came before you, like 2008. And when I realized I’d never be the best, I realized I could be something else:...

  • Ask Anna: How will I ever afford a wedding?

    Ask Anna: How will I ever afford a wedding?

    I'm a 26-year-old lady dating a 31-year-old man. We've been dating for over 4 years now. He has been in and out of jobs, presently he is jobless and broke. He is not good with money either, doesn't know how to save, and is always in debt. I'm becoming worried that I might have been wasting my time...

  • 'Baby, It's Cold Outside' gets updated for the age of informed consent

    'Baby, It's Cold Outside' gets updated for the age of informed consent

    I can imagine a time when it seemed darling for a husband and wife to go around singing a little Christmas ditty about a randy man trying to seduce his reluctant date, as composer Frank Loesser and his wife, Lynn, apparently did in the 1940s. And I can give thanks that I didn't live in that time....

  • How to raise the cash to afford those Cubs season ticket price hikes

    How to raise the cash to afford those Cubs season ticket price hikes

    The Cubs announced that season ticket prices will go up almost 20 percent next year. Before you throw in the W flag, let's spitball some ways to raise the cash to pay for some World Series Champ-quality baseball. Cut the subscription cord Netflix. Spotify. Even Amazon Prime. Cancel ‘em. Sure, they...

  • Ask Anna: How can I be sure a sex toy will work for me?

    Ask Anna: How can I be sure a sex toy will work for me?

    How can I find sex toys that fit me well without spending lots of money? They're expensive and not exactly returnable.—Don’t Toy With Me Ask the store clerks for their recommendations, DTWM. They’re there for a reason, and it’s not just to quietly judge you for renting “Big Trouble in Little Vagina”...

  • Threesome Advice Panel: Can I just give my girlfriend cash to buy something that she wants?

    My girlfriend really wants a motorcycle, but I don't know [bleep] about motorcycles. I know about how much it will cost, but she's still unsure about which one she wants. Even when she sees one that she likes, she doesn't try it out because she can't afford it. Is it cool to just give her cash...

  • Super-thoughtful holiday gift ideas for all your 'loved' ones

    Super-thoughtful holiday gift ideas for all your 'loved' ones

    So, it’s time to buy people presents. Again. And while there are very concrete rules about what not to get the special people in your life, getting it right isn’t always as easy. Until now. Here are the most thoughtful gifts to get for your most cherished loved ones. You’re welcome. Your foodie...

  • Ask Anna: I've fallen for someone who's never dated a girl. Am I being friend-zoned ... again?

    Ask Anna: I've fallen for someone who's never dated a girl. Am I being friend-zoned ... again?

    I met this woman about two months ago on a camping trip and fell head over heels for her. At first it looked like we were flirting a little. But she was with a boyfriend, so to me it was just a game and nothing more. I figured maybe they're an open couple and if anything happens, it would be fun...

  • Threesome Advice Panel: My SO is always late. How can I ask them to fix it?

    Threesome Advice Panel: My SO is always late. How can I ask them to fix it?

    My significant other is constantly late for everything. At first I didn't mind, but it really started to bug me. I just feel like it's disrespectful to agree upon a time and just show up late, especially when it's so constant. When I bring it up, the reply is something along the lines of "I'm just...

  • The Second City's guide to gifts that will ruin your relationship

    The Second City's guide to gifts that will ruin your relationship

    Whether you’re more of a Black Friday elbow-thrower or a Cyber Monday add-to-cart-er, no one’s safe from dropping mad amounts of dough on holiday gifts. Even the most thoughtful among us know that “It’s the thought that counts” is a bunch of bull, the really expensive kind of bull that people like...

  • The Second City: Creative ways to hide your post-election crying fits

    The Second City: Creative ways to hide your post-election crying fits

    Whether you’re ready to move on or not, regular life is carrying on in our post-election world. Hey, you can go for as long as 45 minutes without remembering the current societal chaos! Perhaps you’ve even smiled once or twice? And then, out of the poorly-predicted-by-Nate-Silver blue, you’re crying....

  • Ask Anna: Can I hook up with my friend?

    Ask Anna: Can I hook up with my friend?

    Dear Anna, I am interested in having sex with one of my friends. Usually I need some kind of emotional attachment for sex, so this works out. The problem is that the attachment between us could be compared to the best attachment on the vacuum cleaner— you know, the one that never comes off the...

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