Category Archives: women

She is a 10- but doesn’t get hit on.

Last night, I celebrated Halloween with a few friends. We stopped by the Roof on the Wit, which was full despite the chilly weather.

Typically when I’m out at a bar I can’t help but watch the crowd dynamics. I like to see who’s flirting, who’s singles, who’s taken and who’s cheating. Naturally, I’m a people watcher and the Wit was giving me a great show. My single friends know that going out with me usually ends up with a long night of questions on their perception of others. I like to know what people find attractive and the best way to do this is to play  a non killing version of the Shag, Marry, Kill game with total stranger as our victims.  “If you could take any person home tonight, who and why?” and “If you had to marry one person here, who would it be and why?”   Not the most professional way to extract information from someone, but guaranteed to be interesting.

The most popular girl in the evening to both marry and shag in the bar tonight was “The Swan”– a tall fit blonde who was a “10” in anyones book. She was wearing what appeared to be a white swan dress with feathers and sequins everywhere. It was classy and form-fitting but not the typical “slutty version” Halloween costume. unfortunately for her she had been sitting surrounded by girlfriends and looking very unhappy all night. I noticed men looking at her, but no one approached.

A little later in the evening I had happened to strike up a conversation with Swan while waiting for the washroom. Swan was out with friends, though didn’t have a date. She also confessed (it’s amazing what a little liquor does) that she felt silly in her outfit, and wishes she had worn something more revealing because none of the men would talk to her.

Being a matchmaker and dating coach I had to let her know that the men were looking at her and attracted to her, but she was giving off bad body language. By sitting with girlfriends on a couch with her arms crossed around her body she was not giving off “come hither” signs.  I told her to look up from her drink more and smile while keeping her arms UNcrossed and just at her sides. I also told her to step away from her group of gal pals, as men are often intimidated of a group of girls. Her choice of outfit was not a hinderance, in fact the costume flattered her and left something to the imagination. The only hinderance was her attitude wearing it. Swan said she didn’t realize she was giving out “No” signals and was going to try to look approachable.

About thirty minutes later I noticed Swan and a zombie getting  to know each other. She had taken my advice and was a few seats away from her friends, giving good body language and appeared to be interested in him. He was digging on her too. She smiled at me when I as leaving, and I was happy to have helped make a love connection for a love hungry swan and blood hungry zombie.

Happy Halloween to my readers! As a treat (not trick) for you, please enjoy 25% off Friday nights (November 4th) Nuts & Bolts Party- follow this link and enter “blogread30” as the coupon code.

Chicago Matchmaker FAIL

Matchmaker fail last night. Really, I don’t fail often so it’s hard to write about it, but a great learning experience. I match at least a couple a week, and I’ve had a pretty good run so far. Some matches are “meeh” some have continued to see each other and some part as friends, but I’ve yet to have a couple HATE each other after 2 hours. especially a couple I thought had so much in common.

He’s a pretty boy, well brought up, high maintenance. Tall, broad shoulders with a deep voice. Very attractive. He works in a stressful and very time-consuming position in the financial district, doing something he doesn’t really love, but it is what is expected of him to do. He says he’s looking for an equal in the relationship, a true partner. Someone who understands his long hours at work and waking up at 5 in the morning to hit the gym, says he wants someone who has also “made it” in the world and has a strong will.

She’s hot. Really, really hot. But not in a sultry way. More in the high maintenance way. She’s also very intelligent and doesn’t take no for an answer. She’s a bit of a ball buster. She told me she wants a man who knows who he is, knows whats he’s doing in life and is ready to start a family- but understands her career is very important and won’t mind if she works long hours. Shes the “everything” kinda woman who you imagine wakes up after 4 hours of sleep every night looking just as amazing as ever and is ready to conquer another day.

Disaster. What I found out AFTER the date is the truth about what they both want. Unsaid expectations make it really hard to properly match a couple. I think that many people have expectations on a potential partner that even they don’t realize.

What he actually wants is someone more like his mother. A woman who worked in real estate until she had her first child and then gave it up to raise a family. He wants someone who is smart, attractive and has it “together” but is willing to give up the career in order to take care of him and the family.  He does want someone strong, someone active and a ball buster, as long as it’s not his balls.

She…. she’s a different story. Raised by a single mother and as an only child, she expects to and wants carry on with her career after having a child. She feels like there always needs to be a “plan b” in case something goes wrong, and giving up her successful career isn’t an option to raise a family. She turned out alright with her mother working long hours, there is no reason why she can’t carry on the tradition. She is attracted to strong men, but is very competitive and truly wants to out do her partner- not in an angry way, but in a way that says “Look! Your great, but I’m great too!”

Disaster. I should have known better. Oh, she’s a republican (die-hard) and he isn’t involved in the political scene (much to the dismay of his family). That was a deal breaker waiting to happen.

Dating tip: When back out in the dating world, it’s important to really know what you want and what sort of future you want. When you can describe how you see your life in the next 5 years, and what sort of partner will make you happy, it’s much easier to find the perfect partner.

So…. about the date.

I’m a fan of laid back “first dates”, and asked the two of them to meet at a local coffee shop at 7pm. They had each others photo and phone numbers.  Both were excited to meet and when hearing about each others backgrounds and traits, were comfortable with the idea of meeting.

He said “Jill, she was 10 minutes late and I was talking to a couple next to me whom I’ve seen around before in the neighborhood. When she came in, I recognized her immediately and thought she was even hotter in person. Until she sat down with a scowl on her face asking who I was talking too… I thought Damn…. not one of these types.”

She said “I was running late and tried calling him but my call went straight to voice mail. When I got to Starbucks, he was sitting across from a pretty cute, younger girl with his arm on her shoulder, laughing it up. I wasn’t jealous, but I was annoyed already at this point.”

Then they both go into details about arguing over the national debt, the Rahm inauguration, whose job is more time consuming, etc etc etc.

FIRST OFF! Don’t talk about politics! Jeez people. Sex, Religion, Money, Family Disaster and Politics. STAY OFF THOSE SUBJECTS on a FIRST DATE!

to be continued…

Getting asked out is hard work! (Girls only!)

Girls, do you think just sitting on the bus with your nose in a Kindle is going to get you a date on Friday night?  If you answered yes… well… you better be Megan Fox in a bikini on a crowded 157 bus, otherwise it probably isn’t going to happen.

 Getting asked out or becoming approached is hard work, don’t let anyone tell you different. Let the man know you are interested… make it easier to make the approach, show him you are available for conversation and you won’t push him away with that “I’m taken” or “I’m a lesbian” line women are known for. How do you do this? Easy… 1-2-3.

1. Smile  

The best smile in this situation is the “coy” smile. Eyes down… then back up- glance at him and when he catches you, wait 2 seconds and then glance down and smile (closed mouth little smile… like you just thought of a funny joke at a funeral and don’t want to be disrespectful) – He’ll see this and be on the seat next to you shortly… trust me.

2. Open Arms, Open Heart

Don’t have anything in your arms. No phone, no book, no stack of paperwork, no burger from Epic. Nothing! If… if you are on the bus or another spot where you just have to have something, make sure your arms aren’t crossed, the book isn’t clutched tightly in your hand in front of your chest or under your nose. Your phone is not pressed against your ear or attached to your fingertips for quick texting. Nothing should be blocking the energy between you and Mr. Right.

3. The Bump

Warning! For experienced Minglers ONLY! You’ve made the smile, the eye contact and you’re not buried under your book, but he still hasn’t taken the bait? The last measure is “The Bump”. It’s a crowded bar or bus and he’s just a few feet away. You’ve made eye contact once or twice but he hasn’t approached. Find a reason, any reason to get closer to him and gently… causally bump into him. As you brush his arm in a quick apology walk away. If he’s smart he’ll be thankful that you made it easy for him to approach. If he’s a bit dense, he’ll just be happy for a reason to approach!

Let him find you in a bit to ask if you’re okay, he didn’t mean to bump into you(If he only knew!).  Take the conversation from there, but always let him think he did all the hard work!

Happy Mingling!

P.s. Check out the upcoming Singles Events to try out your new “approach” skill!


Jill Jackson

How baseball is like dating. 5 dating tips for Chicago singles

Spring is in the air. Its baseball season, love is blooming and the short shorts are coming out! (Time to get back into the gym!)

Here’s a couple of tips to get you into the season.

If you are a Chicago Single, you are going to want to check out the baseball themed singles party we are hosting May 27th at Fado in Chicago.  You’ll be mingling with 80-100 local singles while trying to earn raffle tickets for some awesome gifts!

Continue reading

I just met Mr. Right… for you

 I have the unique view into many single mens (and womens) dreams, hopes and desires as a personal Chicago matchmaker and ladies, let me tell you that the good ones aren’t all married or gay. Just today I sat down for a first meeting with a successful man in his mid 30’s.He’s attractive, just over 6 feet with blonde hair and blue eyes. He is built like an athlete but doesn’t spend time in the gym though he does run ever morning rain or shine. Don’t worry ladies, he owns his home and gets along with his mother and his ex mother in law, he hates to cook but loves to clean. This catch has a great personality, puts people at ease with an upbeat personality and light-hearted humor.  He also hasn’t had a date in just over a year.

Why?  Because he doesn’t believe a great gal would want to date a single dad who went through a bitter divorce. He has full custody (that he didn’t have to fight for) and raising a five-year old daughter consumes most of his free time.

As a matchmaker I get to see into people’s life, they share things with me that they may not share with even their best friends. All the guys in the office think Mr. Right is dating a new chick every weekend. He says he has never told anyone he’s been on dates, but people assume and he never wanted to squelch the rumors. In his own words “The dating life the buddies at work think I have is much more exciting than what the truth is, so I never really set them straight.”  He won’t go out to speed dating, or even a nuts & bolts party because he doesn’t know what to do or expect and frankly, he’s scared. This is where I come in. I get to learn a little more about Mr. Right and help introduce him to a great match.

The first meeting will be casual, I’m a huge fan of a first date activity such as mini golf, ping-pong, bus tour of Chicago, etc. The activity will give them something to 1) talk about and 2) do. Having a three-hour dinner date sitting across the table from a total stranger can be very intimidating, especially for a guy who hasn’t been out on a date in a year. I’ll let you know how his first date goes!

It’s nights like tonight that I hate being single.

An e-mail I received tonight and reprinted with permission. Do you ever feel like this?

Dear Matchmaker:

It’s nights like tonight that I hate being single. 10pm and I’m looking for someone to talk to, someone to cuddle up next to. Thoughts of heading to the local pub across the street enter my mind… maybe I’ll meet someone and sparks will fly. This thought exits just as fast as it enters after I remember the crowd that usually mills around on a weekday after 9pm. Maybe I’ll walk down to Starbucks and start a conversation with that cute guy who I always see sitting in the window seat.  Who am I kidding… I’m 34 years old, way to old for those kids who sit around coffee shops.

I’m tired of cooking for one. I’m attractive and skinny. I am not socially awkward. I have a great group of friends and I’m not a “man hater” or “gold digger”. I just can’t seem to get men in my age group interested in me. It’s like they glaze over me to look at the girls who are 10 years younger… I didn’t think 34 was to old to date, but now I’m starting to wonder.

I’m getting older by the minute and don’t want to stay alone. Do you have advice for someone on nights like this?

P.s. I am coming to the event downtown, so I do try to do “singles events”…


My reply: (After I asked and got the okay to post)

For nights like this…. first off, don’t run out to the bar just to find someone to take home for the night! You are lonely, not horny (well, maybe both… ;p) ) Being lonely is a fixable situation and by looking over your profile, you are going to be an easy gal to find a date for!  First things first, please don’t start talking about how “old” 34 is. YOU are just entering your sexual PRIME baby!  Here is a few ideas to get you cooking meals for two soon!

  1. Change your path.  Literally. Take a new route to work. Take a different bus. Stop at a different Starbucks. The trick here is to KEEP YOUR EYES OPEN! Smile, make small talk and MINGLE with new people, enjoy the new visual sensations. One of my favorite things to do is to eat breakfast at a different local diner every morning. 6 am- you’ll be one of the few people there. Find a diner with a counter, order your coffee and before your check comes I’m going to guarantee you’ll have met 2-3 new people… they might be old, might be gals or might be gay, but every new person you meet makes your social circle that much wider. With a wider social circle comes new (single) friends to meet!
  2. Wear Red. Lame tip? Well, it’s proven to attract the opposite sex. A proven trick up your sleeve never hurts. 😉
  3. Research. Spend the night researching upcoming events in your ‘hood. It will give you something to do with your night and keep your mind off other things. Find an event that should attract the type of men you are interested in. Plan you attack – what will you wear? What single girlfriend will you bring? How will you introduce yourself to the man of your dreams? Think positive!
  4. Call a friend. Not your mom. At least from my experience, calling Mom when you are down about not having an SO (significant other) can be one of the worst things you can do. Moms are well-meaning and can give great advice, but sometimes you want kind words, not advice. Actually,I want to change this to Call your dad. He’ll probably threaten to kill any man who doesn’t jump on the chance to date his darling daughter, and gush about how amazing you are.  That always makes a girl smile!

Can’t wait to meet you! Keep your chin up sexy!!!!!


Anyone else interested in having some non professional advice? I love to give it and you don’t have to take it!

E-mail me @ or find me on Facebook (Jill Jackson), Chicago’s matchmaker and singles events planner. Hope to see YOU at one of my upcoming singles parties.

 Check out upcoming events on the Mingle Around website. Follow me at Twitter @MingleAround

Why’s he single?

As a Chicago matchmaker, I often run into objection from my singles looking for love when I describe a person that I think would be a good match. My favorite objection is “Well, if he’s so great, why’s he single?”  Ladies…. come on! While constantly looking for negative you’ll be missing out on all the positive. 

Why he’s single (Perspective from some of my single ladies)

  • He’s not single. He’s married with 6 kids and a wife who has no idea what kind of scum bag she’s married to.
  • He’s a liar.
  • He’s a cheater and a liar.
  • He lives at home with his mom.
  • He lives in his ex wifes basement.
  • He doesn’t have a job. Or he does have a job and he’s a con artist.
  • He is unattractive.

Why he’s single (The truth)

  • His wife passed away 2 years ago and he’s just now getting back into the dating world.
  • He spent his 20’s and 30’s building a business and spent little to no time finding a date.
  • He just got dumped. But his ex swears up and down that he’s a great guy.
  • He hasn’t found the one.
  • His last girlfriend didn’t want kids.
  • He chooses to be.
  • He broke up with his last girlfriend because she cheated on him.

The truth can be boring. The truth for why great guys are single fall under the same categories as why great girls are single. Not all the good ones are taken (or gay)… next time someone wants to set you up, say yes. A good single man isn’t hard to find if you open up your eyes!

Ready for a good match? Come to a singles event in Chicago. Visit and find a party near you!



All men want is sex. Dating, Chicago style.

“Every man I meet wants one thing.”
“All women are the same… looking for a free ride.”
“Every man cheats.”
“Every women changes after they get married.”

If I hear these lines one more time I think I’m going to puke. Not very professional, I know.  Being a Chicago matchmaker is much more than finding the perfect woman for a certain man.  Almost everyone I’ve worked with has had hang ups that come from past relationship pains or misconceptions developed from watching negative relationships with loved ones.

I’m going to say something that might blow your mind….  those lines above are true;  just as much as they are false. WAIT… hold your hate mail…

People have a need, a desire, a want for physical connection (sex). People would rather marry or date someone with enough money to support both of them. People do change after they are married. People do cheat.

The problem is that many singles (you?) like to use those lines as a false security. They stay away from relationships because “every man I meet only wants one thing”.  When friends ask how the dating life is going, many people find comfort in those lines.  There is nothing wrong with YOU if every man only wants to *&^# your brains out… you’re the good girl who is staying pure and not dating until you find “the one”. So being single is suddenly a better option than beating these men off with a stick.

Don’t use this false security! It’s a line. A lie. There are millions of GREAT men and women. Not only are these men and women honest, commitment focused singles, but they are attractive, confident and at the top of their career.  How do I know? I meet them every day. I have lengthy discussions with them and get to know their character and past. I know some personally very well. These are people who would rather get to know you well before sleeping with you, who don’t cheat, who don’t want you for your money and who won’t do a 180 after the ring is on the finger.

These people are the majority. The liars, cheaters, gold diggers and losers you’ve been dating are a minority. Don’t give up on dating just because you have found a few bad apples over the years!

If you are finding it hard to meet quality singles, come out to a Mingle Around event. The events are low key, laid back and fun. They also draw out Chicago’s sexiest singles.  Bring a single friend with… mix and mingle and enjoy the night. There is a HUGE Nuts & Bolts party this month at Fado’s downtown and a few speed dating events. Come out and enjoy the night. Just leave your hang ups at home!


A great wing woman is hard to find!


I think that every women needs a good hairdresser, a perfect black dress, a pair of heels that will last the night and a  great wingwoman. A good wingwoman is one of those girlfriends that you can call on Friday night 7pm and she’s already ready to go out. She doesn’t “box lock” and won’t get jealous if you score and she doesn’t.

A friend won’t tell all your other friends about that gross guy you made out with when you had beer goggles on. A wingwoman will stop you from making out with him. 

A friend will hold your hair back if you’ve had a little too much to drink. A wing woman will make sure you don’t drink too much.

A friend won’t box lock you out when talking to that cutie from South Carolina. A wingwoman will find that cutie’s twin brother and start conversation with both of them for both of you.

Most of us have a great group of fun female friends that we love to hang out with. As luck has it typically these friends are usually  married or in serious relationships.Though spending the night out with them can be fun, it doesn’t always get the job done. All they want to do is get out of the house and relax, while you might have ulterior motives on you mind like finding the love of your life or at least a date for next Saturday night. These married girlfriends are notorious for accidentally box locking and for picking Friday night hang out spots that aren’t always packed with single men. (Have you ever tried to find a suitable man at a Friday night martinis and manicure followed by the ballet?!) Also, hanging out with a group of girlfriends can be very intimidating for most men to approach.

Your best bet for some hot Friday and Saturday night action is finding a like-minded wingwoman. Look for a woman who has different taste in men. She likes blonde jocks and you like dark-haired musicians? Great team! You love geeky pencil pushers and she loves blue collared construction types? Wonderful! Let the games begin! She may never understand why that man in the corner with the eyeliner and band t-shirt on turns YOU on, but you’ll never understand why that guy with no  neck and 20inch biceps just turned her head.

Where to find  a good wing woman:

  • At a singles event. Caution! Women at singles events are known for being territorial and may be cautious of your intentions.
  • A hip work out classYou’re both busting your butt to look hot on Friday night, might as well do it together!
  • Alone at a trendy bar. She’ll be sipping on something fun and looking super confident. Have you seen these girls? They are a rare breed and typically don’t work in a team, but if you are able to impress them with your uber-cool personality and exciting plan for the weekend you may have just found a best friend for life.
  • A friend of a friend. A safe bet and usually easy to find. Facebook is the way to go.
  • While doing a new hobby. Websites like are great ways to meet new friends, just type in an interest (book clubs, whiskey tasting, karaoke) and you’ll be introduced to 100’s of similar people!
  • Dining out. There is this website called that sets you up with 12 other random people. A dinner out is a great way to meet someone and to tell if she has wingwoman potential!
  • A wingwoman party. From time  to time I host wing women parties. You’ll meet 10-20 potential great wingwomen in one fun evening.  



    Getting crazy with my wing woman!











You’re so vain. I bet you think this post is about you.

Girl at computer

Searching for love in all the wrong places.

Online dating can and will break even the most self-confident person down. Winking, gifting, messaging, viewing and chatting with someone (or lots of someones) that are interested one day and gone the next can be frustrating and might cause a sort of confidence bust.

I’m here to tell you that it shouldn’t. Online dating is the freak show of the dating world. Really popular, fun to watch and can be even more fun to participate. You’ve got 1,000’s of people listed as single. A smorgashboard of potential suitors. The choices can be just too much. Today you can e-mail men who make over $1,000,000 a year and don’t have children. Tomorrow you can email only men who are artists and live at home with mom and dad. Too much choice can be debilitating.

I’ll never be able to explain why people don’t return the wink or the e-mail. I don’t want to. There would be over a million reasons explaining it, but chances are it wasn’t about you. Maybe she only dates black men. Maybe she is looking for someone with kids. Maybe she hates dogs and you’ve got one in the photo. Maybe she hooked up with her ex boyfriend last night and is hoping that will pan out. Maybe she only dates PhD’s. Maybe she’s only online to make her ex jealous.

Who knows. Who cares?

yeah. I know, you do.

Just keep at it. Don’t let online dating be your only social networking though. It can start to be demoralizing. People can be crueller online, thinking they are hiding behind a wall of security because you aren’t face to face. People can also be who ever they want to be online. They can be the conceited bitch or the player, even if in real life they are pussy cats or guys who let the last girlfriend walk all over them.

If you are constantly rejected online take a close look at your profile. Have an honest friend review it. Did you say something that makes you look like a total ass? Does your profile picture of you in a giant funny fake mustache (really popular for girls on OKcupid I’ve noticed) kinda make you look like a freak? Tweak the profile. Change your approach. If something isn’t working don’t keep doing it. But please, don’t give up on dating, just because your online dating world isn’t holding up to what you hoped it would be. Remember in on-line and off-line dating it isn’t always about you.

Get out of the house, get off the internet and Mingle with local singles. Really. You don’t have to be at a dating event (even though MingleAround does have some great ones coming up!). You can mingle at the supermarket, the zoo, the movies, the art gallery. You can mingle at work (proceed with caution) or at your friends upcoming birthday party. Just get out and do it.