Category Archives: men

Where are the Chicago Single Women? (Great pick up bar)

A great Singles Pick Up Bar - Mingle AroundOkay, I hate the idea of a “pick up bar”, but I just have to say it- I found a great Chicago “pick up” bar!I went to The Joynt last week and again this week for work related matters and the place was SWARMING with gorgeous single ladies. No rings on those fingers, guys!

It’s kinda my duty as a matchmaker and social event coordinator to inform YOU about these things, so here I am, telling you. Listen up!

The Joynt is a swanky retro styled piano bar in River North, Chicago. It’s upscale, but not overly pretentious. The guests are classy and very attractive. This place has live music every night, which keeps the ladies dancing and keeps them coming back for more! Don’t fret about going alone, the place is so busy that no one will notice if you’re sitting at the bar by yourself, of if you’re with a huge crowd of friends.

Dress code- I’m not sure if there was a “dress code” but the ladies were all dolled up, the men were in suit jackets and dark jeans (God, I love that look!)

Other notes- If you want a little more privacy and a quieter space, head downstairs. There is a “lounge” area that’s much more chill.

If you’re striking out at the  Joynt, there are about 10 great bars in that area for you to hit up next. But if you keep striking out, you might want to consult a matchmaker or a date coach to see if there are some things you could tweak to improve your skill.

Best of luck!

Please, email me if you know a great “singles bar” in Chicago. I’ll check it out and write a little blurb! Also, check out our upcoming singles events. No need to find a singles bar if you know someone who hosts great singles events!

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.

Picking up girls at Lollapalooza

Lollapalooza: More than 130 bands and artists on eight stages play 11:30 a.m.-10 p.m. Friday-Sunday in Grant Park, Chicago. Over 100,000 people expected… maybe your Mrs. Right will be enjoying Muse with you.

Concerts and festivals like Lollapalooza are one of the more difficult places to meet a girl but can be one of the most rewarding also.

Why the cards are stacked against you

1.    Beer and E. Drunk or high might be fun for a bit, but not girlfriend material.

2.    They are there with friends. Picking up a girl within a group of girls is hard but picking up a girl at a festival surrounded by her besties is almost impossible. She’s there to have fun, not get a phone number.

3.    It’s loud and packed. She is going to have a hard time hearing your great pick up line that you’ve been working on for the past 10 minutes. What’s worse is when you have to yell it 3 times before she hears you.

4.    She’s not local. Unless she’s looking for a Lollapalooza fling she probably isn’t going to be looking to exchange facebook information with you when she lives 800 miles away.

How you can make it work

1.    Be the planner. Pack sunscreen, a soft cooler with extra water bottles, a LARGE blanket. Share what you’ve got with her group of gals and she’ll be lying in your arms enjoying the things she forgot to bring by the time Girl Talk is playing.

2.    Don’t talk to her during the set. She paid big bucks to see Coldplay. Don’t ruin it by asking her what she does for a living. Watch the band, look at her and smile. When they play Yellow and she’s been giving you the eye all night slyly sneak your arm around hers… (warning… this is an advance move and only try if you’re sure she’ll respond positively!!!)

3.    Ask her and her friends out to one of the after parties. Follow this link for a great list of Lallapalozza after parties. Make sure you are on the list with a few plus ones. Grab a cab together and get to know her better.

4.    Don’t be “that guy”. Really. Us girls hate that guy. If you can’t hold your liquor, get in a fight at 2pm or pass out drunk you have no chance with her. Be the (semi) sober one who makes sure she gets back to her hotel safe.


Good luck and enjoy!


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…

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!

How to put your bolt into a nut. (Nuts and Bolts Party info)

How dare the host give you a tiny bolt? Really, come on now… was she trying to question your masculinity? You just saw that guy in front of you get an 8 inch bolt with fancy threading and he obviously doesn’t know what to do with it. … yet you get this tiny 1 incher. Jeez. …. now what?

Well, now you walk up to that leggy blonde who just swaggered by you and you politely ask her to see if your bolt fits into her nut. Without laughing. Or making a comment that your…. ahem… real bolt is much larger… *cough* *cough* *wink* *wink*.

Hopefully it fits, but if it doesn’t fit you don’t need to move on to the next girl, what you need to do is ask her how the night is going. How did she find out about the party? You know, get the conversation moving. If she responds positively to you and even asks you a few questions, then offer to buy her a drink or to sit down in the private booths to talk more.

What if she doesn’t act interested or even states she needs to move on to find a matching bolt? Well, you move on to the next girl too. Bid farewell and let her know when she has a slightly smaller nut to come find you.

Then move on to the next girl who tickles your fancy!

The next “Nuts & Bolts” party is March 25th. Its at Fado Irish Pub in Chicago and starts around 6:30/7.  Tickets online are $20, includes light appetizers at 7pm, drink specials, live music after 9pm and a huge organized singles events. Tickets at the door are $30. Don’t be late…

You can purchase tickets at or but do it soon or else all the good nuts will be taken 😉

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!


Chicago Date Ideas #365

Every girl I know wants to be taken on those carriage rides in Chicago, up and down Michigan Avenue. You know… those slow horses that cause you to miss the light that are filled with tourists and 18 year olds on prom night? Well… thats what she wants to do tonight. I Promise. Rates start at $40 a half hour (may be negotiable, but don’t haggle in front of your lady). It doesnt’ matter if it is a Monday night or a Friday night, surprise her and take her out on the town. After the carriage ride, take a stroll down Michigan Avenue, keep her on the east side of the street if you don’t want her wandering into Tiffanys, but wouldn’t mind wandering into La Perla. 😉 Finish the night with hot chocolate at Ghirardelli Chocolate on 830 N. Michigan. 

Date night cost $60-70  (Ride, tip, hot chocolates)


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.