All The Single Ladies

First dates Archives

Stop making excuses

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

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About a month ago I wrote a guest post on That Happened To Me about a date that I went on. As you can read in the post, the date was pretty freaking awesome and it was the first time in quite sometime that I really wanted a second date. I mean truly wanted to see the guy again. But, the second date never happened even though he pretty much planned the entire thing with me.

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In defense of the shy guy

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

 

Man in boxers crouching

Recently I made a new friend. I kind of use the term friend loosely here as I have been engaging in a little flirtation with him. Read that as I have been flirting my ass off. He knows it and it seems to be pretty mutual.

Anyway, upon getting to know this guy, he has openly admitted to me on more than one occasion that he is a really shy guy - actually to be technical here he is a shy guy who is also on the clean cut side. This is generally the kind of guy that I have a really hard time meshing with and I know it's a problem for other women too.

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Date Night Challenge Week 3: Things haven't gone the way I planned (yet)

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

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So it's week three of the Date Night Challenge. And this week I actually had a date lined up. I say that like I am a little school girl or something but I was actually pretty excited. Frankly, there has been a shortage of really awesome guys asking me out on dates lately - I am not sure why that is.

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Win a pack of FlipMe dating cards

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

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The anniversary for my blog was a couple of days ago which is a really exciting thing for me (don't worry I will post more about that later). So to thank all of my awesome readers I have another really fun giveaway.

FlipMe is a new and exciting way to date/meet people. In fact, when the people over at FlipMe contacted me to tell me about their service, I was extremely excited. As an avid internet dater, it's fun to mix things up a little sometime. After all, you can't put all your eggs in one basket, right?

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A date shouldn't be treated like a job interview

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

Businessman in Meeting

A couple of days ago a reader left an awesome comment on my blog which really made me think. The comment mentioned how a lot of women treat a first date like a job interview which is something that I feel is true. It's something that I will openly admit that I have been guilty of in the past.

Honestly, I wish we could get past this idea that you have to be completely perfect on a date. When I first moved to Chicago, I spent a lot of time dating like that. I have to tell you it honestly wasn't any fun. I mean, one time when I met a guy for drinks the first thing that flew out of my mouth was a comment about how I sweat when I am nervous. Clearly that's not hot in anyway but I also don't think that sort of thing is really that big of a deal. And I am pretty sure that I don't want to date a guy that worries about something silly like that.

I used to beat myself up about things like. And as I was getting ready to meet a new guy I would always go through the list of things that I did wrong on my previous dates. It was exhausting.

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First impressions are exhausting

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

My niece and nephew came for a little visit this past weekend. We planned to go to the Museum of Science and Industry and the Lincoln Park Zoo. As we were getting ready to go on Saturday, my niece picked out what she wanted to wear. She chose a pair of black leggings with a pink and black striped sweater dress mainly because I was wearing black leggings and a black dress and she loves to wear outfits that match what I am wearing. She also decided that she wanted to wear the socks that I bought her when I was in NYC.
 
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A spade is a spade

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

Senior man holding the ace of spades

A couple of nights ago, I had the opportunity to meet with the very talented blogger/writer Disaster on Heels. We had a pretty simple plan - flirt with some guys, celebrate National Singles Week, and of course enjoy the $2 beer special at the Kerryman. The night ended a little early when she realized she had lost her wallet which made her believe that she was living up to her name as a disaster (you can read more about that over on her blog).

She was more worried that she was coming across as that really bad date. You know the one where the person "forgets" their wallet so the other person has to pay. However, the bill was only a mere $20 so clearly that was not her plan. I was really just worried about her finding her wallet because I genuinely felt terrible for her. Plus, when the subject of my upcoming birthday came up she assumed I was turning 25, so I am pretty sure I would have forgiven her for anything after that.

At any rate, our quick lap around the bar to meet and mingle with some savvy single guys was pretty unsuccessful. We tried and I mean really tried but the only somewhat attractive guys were a group of three early 20 something's, one of whom was wearing a pink polo shirt. I wasn't even actually sure guys did that anymore and DOH mentioned you shouldn't do that after Labor Day. And she was a little distracted by the wallet situation. Can you blame her? That is one of my fears right there.

However, earlier in the evening, as we were about two beers in, we were chatting about the chaos (aka our internet dating lives) which obviously led to story swapping. I talked about a guy that I recently met and as I was telling the details I really started to think.

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I'm bored so do you want to go out?

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

Bored man waiting at table in restaurant

We've established that some guys need to learn what a date really is (and also a better place to meet women off the internet). Well, I kind of feel like we need to go into this whole asking a girl out on a date thing. I am just going to get straight to the point here, the words "I'm bored" should never be followed by "would you like to meet" (or any other derivative of that).

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Sitting on my couch is not a date

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

Destroyed couch

I've had a epiphany this week. Actually, back up for a second. Technically I have been thinking about this for a while, I just feel like it was fully confirmed this week. If you read my blog, you know that I am pretty open minded when it comes to dating and by no means am I a prissy princessy kind of girl. I have to be honest here though guys, sitting on my couch (or your couch) is not a date. Really, it's not.

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Guest post: So...do you want my phone number or what?

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

It's time for another guy to guest blog on dating rules. This time we have a post from Dennis Frymire about that whole "you have to wait three days to call a girl" rule.

Woman offering piece of paper with her phone number
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Planning a date in Chicago? Here are this week's spots

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

I Heart U

Chicago Center for the Performing Arts
777 N. Green St.

Fridays at 8 p.m. (ends June 25)

Kind of a romantic comedy, only better. A sketch revue about romantic relationships. Cost is $10

Chef's Cooking Class

Wave
644 N. Lake Shore Drive

June 5 from 2:30 p.m. to 4:30 p.m.

Executive chef Kristine Subido leads a culinary demonstration on how to make Indian and Middle Eastern street food followed by lunch. Includes wine pairings, one cocktail and recipes. Cost is $60 and RSVP is recommended.

Eastside Millennium Art Festival

Michigan Avenue and Lake Street
100 E. Lake St.

June 4 from 12 p.m. to 5 p.m.
June 5 from 10 a.m. to 5 p.m.
June 6 from 10 a.m. to 5 p.m.

It's summer, so why not try one of Chicago's many festivals? Here you can browse works artists including ceramics, fiber, glass, jewelry, sculpture, mixed media, painting, drawing, photography, wood and furniture. And the best part? It's free.

Italian cooking class

312 Chicago
136 N. La Salle St.

June 5 from 12 p.m. to 2 p.m.

Yes, I know another cooking class. Learn how to make homemade pastas with executive chef Luca Corazzina and his mother. Includes appetizers, recipe cards and a bottle of olive oil to take home. Cost is $45 and RSVP is required


 

Planning a date in Chicago? Here are this week's spots

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

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So my man Andy Avalos on NBC told me that it will be close to the 80's this weekend. For the city folk that probably means somewhere around 72-ish. Point being that we have a nice weekend coming up in Chicago. So if you are planning a date this weekend then check out some of these ideas.

Also, I say it's a great weekend to take a walk on the lakefront or check out the Lincoln Park Zoo or ven better, head out on Sunday for brunch. Don't know where? Well have no fear because the Queer Guy Tells It Straight has you covered with his weekly brunch spot.

Happy dating!

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Guest post: Don't be too available dammit

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

Since I have such a fun time talking about all the dating rules (and how much I think most of them are crap), I feel kind of like I need a guy's point of view. So I've asked some of my most favorite guy bloggers to tell me what they think about some of them and over the next few weeks I will be posting their thoughts. First up is Alex from the Urban Dater (a very awesome website about dating and relationships) who talks about being too available, or as he's titled it "Don't Be Too Available Dammit!".

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Planning a date? Here are this week's spots

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

 

Chicago Skyscrapers

I'm not a big fan of dinner and movie dates. Though sometimes planning a date can be a little difficult. However, this is Chicago and there are quite a few awesome (and inexpensive) things going on this weekend. So if you're struggling with what to do, here are a few ideas.

Happy dating!

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Please meet me in person before inviting me into your bed

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

man sits on the bed in de sleepingroom

A little while ago a friend wanted to fix me up with another friend and all the guy could talk about was having me over to his place. And he wasn't talking about cooking me a little dinner and playing some trivia on the Wii (read that as he just wanted to have sex with me). I guess he's had an issue with some women that are just too attached after the first date. So he's not to keen on the whole date thing. Apparently now he is punishing all women, including me.

This is not the first time I have been in this kind of situation.

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Planning a date this weekend? Check out these spots

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

 

France, Paris, young couple outdoors, man holding flowers behind back

Meat the Chefs

Paulina Market
3501 N. Lincoln Ave.

April 24 from 10 a.m. to 2 p.m.

Sample dishes prepared by David Digregorio, partner and executive chef of Osteria Via Stato. Bonus is this event is free.

Wine tasting

The Melting Pot
609 N. Dearborn St.

Fridays and Saturdays from 6:00 p.m. to 10:00 p.m.

This is the perfect kind of thing for a "just meeting" for a drink date. Includes two tastings each of red and white wines. And bonus, it's free too.

Whirled News Tonight

iO
3541 N. Clark St.

Saturdays at 8 p.m.

Who doesn't love catching the evening news? Audience members select news articles to inspire this satirical improv show. Cost is $14.

$50 five-course dinner with wine pairings

Sundays, Mondays, Wednesdays, Thursdays, Fridays, and Saturdays from 5 p.m. to 10 p.m. (ends May 9)

Chalkboard
4343 N. Lincoln Ave.

Here you can dine on a menu of: tuna sashimi spring roll, arugula salad, scallop with vanilla mayo, roasted halibut with crispy pork belly and bacon ice cream. Sounds tasty and (fairly) cheap.

Gold Coast Film Festival

Royal George Theatre Center
1641 N. Halsted St.

April 24 at 7:30 p.m.

The sixth annual showcase of Chicago amateur cinema showcases low budget and short films. This cost is $40 to $50, which includes two drink tickets at a pre-party at Landmark which starts at 6 p.m. The restaurant also offers a $35 three-course pre-festival dinner and an after-party until 3 a.m.

The Sunday Night Sex Show

The Burlington
3425 W. Fullerton Ave.

Every last Sunday of the month from 7:30 p.m. to 10 p.m.

Allen Makere and Robyn Pennacchia answer questions about people's love life and host humorous, sex-themed readings by local writers. Also includes trivia games and prizes. There is no cover and there is a cash bar.

Planning a date in Chicago? Here are this week's spots

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

Close-up of a young man tying a necklace around a young womans neck

 

Ctrl+Alt+Deport

Donny's Skybox Theatre
1608 N. Wells St.

Saturdays at 7:30 p.m. (ends May 15)
Except April 24

Latino cast Salsation Theatre Company performs a new sketch show which looks at the the ways in which technology assists and hinders personal and community relationships. Cost is $12; $10 for students.


The Super Happy Fun Show

The Cornservatory
4210 N. Lincoln Ave.

Saturdays at 11 p.m.

Corn Productions ensemble members Julia Weiss and David Kaniuk host an improv talk show with performances by a rotating roster of guest comedy troupes. Cost is $ 10 and it's BYOB.

The Wild Party Variety Hour

Prop Thtr
3504 N. Elston Ave.

Every 3rd Saturday of the month at 10:30 p.m.

Local performers Nathan Paul and Marvin Eduardo Quijada host a cabaret featuring burlesque, modern vaudeville, solo performance, stage combat and more. Live music follows. Cost is $10.

Spa Week Chicago

Daily (ends April 18)

Get select treatments for $50 at dozens of area spas and salons. Contact individual spas for appointments. RSVP is required.

Participating spas include:
Amber Spa
Aniko Salon & Spa
Channing's Day Spa
Continuum Studio
Exhale Spa
Kiva
Ruby Room
Shen Shen Health & Harmony
Siren Salon
Spa Space

Modern Vintage Chicago Spring Clothing and Jewelry Explosion

Journeymen Plumber's Hall
1340 W. Washington Blvd.

April 17 from 10 a.m. to 7 p.m.
April 18 from 10 a.m. to 5 p.m.
 
Check out indie designers and vintage vendors. Browse clothing, home furnishings, fashion magazines, jewelry, handbags and other accessories. Includes cocktails, informal modeling and styling and an on-site seamstress. Cost is $8-$10

Pizza-cooking class

La Madia
59 W. Grand Ave.

April 17 from 11 a.m. to 1 p.m.

Learn how to make and stretch artisan dough in the Italian tradition. Includes samples, and some wine. You will even get recipes to take home. Cost is $30 and RSVP required

The Deranged Minds

Water Hole Lounge
1400 S. Western Ave.

Every 3rd and 1st Saturday of the month at 8 p.m.

A stand-up showcase features local comics Marc Peurye, E-Dub, Fearless Armondo, Mike S., Marianna, Krazy Katie and others. As a bonus there is no cover.

Chinese Herb and Vegetable Class

Ben Pao
52 W. Illinois St.

April 17 from 10:30 a.m. to 12 p.m.

Learn how to grow and cook with Thai basil, ginger, cilantro, lemon grass and peppers. Includes a planting pot, seedlings, an apron, lunch and a $10 gift certificate. The cost is $35 and RSVP is required.

Wine Tasting

South Loop Wine Cellar
1442 S. Michigan Ave.

Fridays from 7 p.m. to 9 p.m.

A weekly sampling of five to ten wines with snacks. Cost is $5-$10 

Apparently even crazy comes in threes

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

Hand making three sign

Lately, I have been thinking a lot about third dates. I have noticed a pattern with the guys I date. And then I had a conversation earlier with a woman I know about how relationship milestones come in threes.

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Planning a date in Chicago? Check out this week's spots

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

Couple on a Date

The time has come for this week's date spots. There's a lot of fantastic things going on so grab a date and go check one out.

Happy Dating!

P.S. Want to meet someone to go on a date with? Come out on April 10th to the singles event hosted by All The Single Ladies and Sex and the Windy City.

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Help! I'm on a disaster date

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

Couple yelling at each other

Shows on MTV are quite entertaining and since I was sick today, I caught a whole marathon of Disaster Date. In case you don't know, the idea behind the show is exactly what the title suggests. People hook their friends up on blind dates who do everything on their list of dating don'ts. The date and everyone else involved are all actors. Then the friends are given one dollar for every minute they stay on the date, the goal being for the date to last an hour.

 
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Planning a date in Chicago? Check out this weeks spots

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

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I am sure you are tired of me making references to the weather and dating, but spring officially begins this Saturday. While the weather might not cooperate, there are still some awesome events going on. So grab a date and go check them out.

Happy dating!

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Planning a date? Here are some things to do this weekend

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

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Most of the city will be overdosing on all of the green festivities this weekend but that doesn't mean there is nothing to do on a date. Here are some ideas if you still want to be green (that don't involve getting completely smashed by drinking green beer all day) and a couple if you want to skip out on all the action altogether. Let's face it, that's probably not the best idea on a first date.

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If he doesn't want to ask you out, try making him jealous (Really?)

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

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I have started reading a new dating book called Date Like A Man by Myreah Moore and Jodie Gould. So far the book hasn't been that bad but then again, I am only 40 pages in. The main idea about the book is just what the title suggests, telling women how to "date like men." Basically the theory is that since men have so much fun dating (and aren't dead set on finding a partner for marriage) that women should date this way too.

 

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Planning a date this weekend? Check out these spots

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

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The sun is finally out in Chicago and, as an added bonus, there's talk it might actually be in the 40s this weekend (heat wave, I know). So since I am giving you some great events that are going on around the city that means there is no excuse to not have a great date this weekend.

Happy dating!

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Chicago singles scene: Speed Dating Events

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

 

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Speed dating is a great way to meet other singles (I am pretty sure I have said it before). Luckily there are a ton of places that offer it for all ages throughout Chicago. Check out one of these events and maybe you can snag a date. Plus, since I will be giving you a few date ideas today that gives you a perfect excuse to get out and find someone to actually go on a date with.

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Always try to keep an open mind when dating

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

 

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Let me start off by saying that I am not a big fan of The Bachelor/Bachelorette. Honestly, the idea seems completely ludicrous to me. I mean come on. You group the "beautiful" people together at some insanely gorgeous location then send them on dates with helicopters, waterfalls and exotic (read that as expensive) foods. Then, in the end, you choose the person you want to marry, probably propose, and then venture out into the real world to make it work.

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Planning a date this weekend? Try one of this week's spots around town

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

 

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There are some fantastic things going on this weekend. So grab a date, brave the cold and get out and have a great time.

Happy dating!

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Who cares who asks who out on a date

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

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Dating is already confusing enough and this whole idea of who should ask who out honestly just makes it worse. I continually read about it in every dating book that I pick up. The consensus essentially is that if you are a woman, you should never ask a guy out. Sure, you can hint around to it and try to convince a guy to ask you out. However, you should never actually ask him out.

This is a concept that I honestly don't understand. I mean did I miss something here, it is 2010 right? With everything else that is evolving in the world, why hasn't this?

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The great date in Chicago: This week's spots around town

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

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Planning a date in Chicago can be a little overwhelming. Let's face it, with the 999 events the city has going on at any given time it's hard to know what to choose.

Well, I have decided to help a little here. Every Wednesday I'll give you some events/ideas that are going on around the city that are sure to make a great date. Anything from great restaurants, to comedy shows, to concerts and festivals. You name it. I'll also include some budget friendly events because just because we are in a recession doesn't mean you can't get out and have a great time (and impress your date).

Also, if you have events that you know of please feel free to share with me by emailing me here.

Happy dating!!

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Have you ever double booked?

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

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Lately, I have heard a lot about double booking dates. The subject came up on a few shows and movies that I have watched lately. Then the other day I saw a couple of posts about it on Twitter.

If you don't know what double booking means, essentially it's having two dates back to back in one day. Now, I have to say that I personally have never double booked. Though I can't say it's because I think it's wrong, it's just simply because I have never found myself in that situation. Generally if a guy asks me out and I already have a date I tell him that I am busy and try to plan something for another day.

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Speed dating? No wait, speed hating

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

If you've ever been speed dating, you know that it can be a little intense. Let's face it, getting three minutes to shine so someone will check the little box that says "yes" next to your name isn't exactly the ideal kind of first date. Though I guess compared to some of my dates that really isn't all that bad and at least you don't have to come up with some clever get away plan if the date goes horribly wrong.
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Should I keep seeing him?

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

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I received an email the other day from a woman I know who is having a little dilemma with a guy she's recently started seeing. Here is the gist:

She met a guy through mutual friends and they immediately hit it off. A few days later they met for a quick drink and then that weekend they had their first "formal" date. Though he ended the date with a kiss she seems a little thrown by him. First, he asked her out via text, which is a huge no no in her book. Second, he didn't offer to pay for any of the date at all. Essentially she isn't sure if she should keep seeing him or not.

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First date etiquette: How to handle public transportation

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

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© Jeremy Atherton, 2006

One reader "Bald Chi Guy" (whose name I believe may actually be Dennis) mentioned the other day that he would like to know the etiquette for ending a date when you are using public transportation. Ah yes, yet another thing first daters have to be confused about.

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The non-drinking guy: Deal breaker or not?

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

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One of my fellow bloggers Sex and the Windy City, brought up a really interesting point the other day when I wrote about drinking on the first date. She asked "what if you like to drink and your date is a non-drinker, is that a deal breaker?"

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Drinking on the first date (when your date isn't drinking)

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

Drunk Girl.jpg

When I wrote for examiner.com, one of my dating don'ts involved the subject of who should pay on a date. More specifically how you shouldn't be rude about paying for a date. Let's face it first date etiquette can be a little tricky especially when it comes to who should pay. It's an age old question and honestly I am not sure if there is a right or wrong answer, it's just something you have to deal with.

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If he doesn't call to get his hat back then he's just not that into you

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

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This is not the actual hat. I am not sure if I would call a woman to get this hat back either.

I feel like I am a pretty smart woman when it comes to knowing if a guy isn't into me or not. You go on a great date, its been a couple of weeks and you haven't heard from him. Pretty clear he is not interested right? Maybe you send him a text or call him and he doesn't respond. Again, pretty clear he is not interested. Generally I feel this is pretty straight forward and I am not the woman who makes excuses about why he didn't call and so on.

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How to end the first date: The worst advice ever

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

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Dating books are a lot of fun. Generally I like to read them out of curiosity, I always wonder what other people have to say about dating and being single. Plus a little advice never hurts a girl right? Lately I have been reading this book called Why Hasn't He Called. Actually, I would like to call it The Cookie Cutter's Guide to Getting the Cookie Cutter Guy since I feel like that title is far more fitting for the book.

As a side note here, I feel like I should sort of defend the corny title here. Actually, I read the reviews on Amazon.com and that is what hooked me. Honestly, I couldn't believe that a book would actually recommend some of the things the reviews said so I had to see to myself. I am almost done with the book and I have to say the reviews didn't disappoint me. They weren't lying at all. This book gives some of the most absurd advice that I have ever heard.

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Deal breakers in dating: The bad first move

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

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When you are dating guys over say the age of 25, it is inevitable that they have been on a date or two. Which also makes it pretty inevitable that they have kissed a girl and probably done all that sexual stuff too. Now, I am sure there is a 29-year-old out there somewhere that hasn't really been on a date with a woman. However, most of them have been around the block one or twice (some of them more times then they care to admit).

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iphone Sleaze Detector App good for singles?

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

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I don't "i" anything. Translation? I do not have an iPhone or iPod. It's not that I have anything personal against these super high tech devices or anything. Really, it's more that I am a faithful Verizon customer and I believe there are plenty of other neat-o gadgets that will play my music that cost a whole lot less.

 

 

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Fun winter date activities in Chicago

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

 

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Time Out Chicago recently put out an article about a few winter tourist activities that even Chicagoans can appreciate and enjoy. The added bonus? Each one would make a fantastic first, second, third, or anytime date. So if you are looking for something that's fun and holiday-centric, I recommend suggesting one of these. Hey it beats the generic dinner and a movie date.
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The rules of dating

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

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Anyone who knows me can attest for the fact that I have somewhat of a rebellious side which means that I don't really like to play by the rules. I am not really all that into labels or stereotypes because I honestly feel that people are people and we should just be ourselves. These are things that I really love about myself but that sometimes can make my dating life a little crazy.

 

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There is no (good) excuse for standing a person up

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

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Stood up. Two pretty ugly words right there. I am pretty sure that's one of the worst phrases in the dating dictionary. It's kind of like dropping the f-bomb in front of your Grandma on Christmas morning. The worst part of it is that you can't really see it coming. I mean I have had it happen when I literally just talked to the man a couple of hours before to confirm plans for the date. How does that even happen? Really.

 

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He's sorry for blowing me off (really)

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

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As I have said before, I am a woman who  gives credit where credit is due. In light of some recent events, I sort of feel like I should tweak my thoughts on the guy from Facebook. Though, I can't really completely retract my opinion on the entire situation as a whole here. Frankly, what happened sucks and there is no denying that. However,  I do also know that doesn't necessarily mean the person sucks, people do make mistakes sometimes right?

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Smart phone feature smart for a blind date

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

Everyone has had a bad date; actually most of us have probably had more then one bad date. We are not just talking about the slightly unattractive date with the funky breath here. No, what I am talking about is the date where the thought of just sitting through a dinner with them makes you want to throw up a little. The total creep package - rude, obnoxious, not attractive, offensive personality, completely mannerless - you get the idea. These are the type of dates that caused the invention of the casual let's go have a drink predate so you can make sure you actually want to sit through dinner with the person.

If you have been on your share of dates like this, it's likely that you have a back up plan to get out of it. I am definitely a believer in the back up plan; it's a necessity ladies (and gentlemen). Of course I will openly admit that I have been a part of plans like this in all my years of dating.

Most people tend to go with a call from a friend. Slightly generic I will admit, but its fool proof. It may be a little harsh to plan your escape before you have actually met the date, but let's face it; there is no politically correct way to get out of this sort of thing. It's awkward and annoying no matter how you look at it.

I found this video on YouTube. The guy is a prime example of the date that deserves the back up plan. So take a look at it, have a laugh and hope you don't have to deal with this on your next date.

 

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Signal for sex on the first date

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

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Generally, I feel that you should go with the flow and do what feels right when on a date. Though, as a woman, sometimes I feel that there is a fine line between whats fun and what is just way too slutty. Which means there are things that maybe you shouldn't do on a first date. Back up for a second, there might be certain things you shouldn't do on a first date if you want a second date.

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Avoid the excuses if you aren't into me

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

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A couple of weeks ago I had a date. It was with a guy who sort of hit on me on Facebook. He read some of the things I had been writing on examiner.com and apparently thought I was attractive so he sent me a message. We chatted a bit, exchanged numbers, talked on the phone a lot and decided to meet.

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