Category Archives: dating advice

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!


Pros and Cons of online dating

Pros and Cons of Online Dating

Many of my Mingle Around clients and singles that I know ask me about my thoughts on online or internet dating and I’m always happy to share my opinion!

Online dating con # 1.

 False Advertising – At least when you’re at a singles event or out at the bar with friends, what you see is what you get….. Unless he’s wearing lifts or she’s sporting a “booty bump” – there won’t be major surprises (at least in the attraction department) on your first date.

Online dating con #2.

Time Wasting– You’ll spend an average of four-six hours texting, emailing, calling and winking at your potential date before a real date is set up. Then add up the time you take to get ready for the date, the commute to the location and then the average two-to-three hour date just to realize there isn’t chemistry (even though he/she may be just as good looking as the photo) and you’re looking at a lot of time and energy wasted.

Online dating con #3.

Privacy- What happens on the internet stays on the internet… FOREVER. The questions that some of the top online dating sites ask are intimate. Some of the questions they ask you- I wouldn’t even ask my closest girlfriends….But people are more than happy to share share and share with little thought of who will see these answers in the future.

Online dating con #4.

Your Boss– Speaking of privacy, you might not want to “match” you with your co-worker or brother. I’ve heard horror stories of both. Makes for awkward family dinners and board meetings. Not only is your profile up for everyone to see but you don’t know who’s profile you’ll run into on your quest for true love.

Don’t think I’m a hater of online dating. I’m not, there are some great reasons to date online. Just don’t make online dating your only source of finding love!


Online dating pro #1.

Gets your feet wet- Many of my clients are recently divorced and are nervous about dating for the first time in years. Try out online dating; the fear of rejection is lowered due to the anonymity of being online. Online dating can be a great way to boost your confidence, especially for woman as the ratio of men:women on these sites lean to the favor of the single female.

Online dating pro #2.

You get to BE SPECIFIC- For those of you who ONLY want to date a Jewish man over 6 foot or a Catholic female who lives 30 miles south of Chicago, online dating can help you narrow your search. There are niche sites for all religions, fetishes, hobbies, ages, and races.

Online dating pro #3.

Cost- It’s typically cheaper to “online date” then to visit a matchmaker or to spend every weekend out at a bar or social event.

Online dating pro #4 .

Deal Breakers- Get to know someone a little more before making your “move”. It’s kinda cool to read the profile of a hottie to scour it for “Deal Breakers” before deciding to pursue them online or not. You can’t really do that at a bar without approaching them, flirting, buying them a drink or two and then trying to get to know them. Plus it’s a dating rule that you shouldn’t ask about many “deal breakers” on a first date, let alone the first five minutes… It’s not like you can just say “hi my name is Jill- do you smoke, have kids, what’s your religion, would you rather read a book or go to a club, and do you like your mom?” Awkward!!!

Good luck on your search for love, lust and happiness. Remember, Mingle Around hosts singles events where you can meet singles in real life— not the internet!




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…

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!

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 😉

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