Category Archives: life as a matchmaker

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!


Dumped on Valentines day & list of parties tonight

I was in major puppy love. Sixteen years old and in love with the most popular senior in high school. We had been dating about two months now, with romantic gestures, letters, poems, flowers, candy and the whole nine yards for the entire relationship. I thought I was in a “so bad it’s good” 80’s movie.

Imagine this naive, love struck girl going into her locker and to her surprise instead of a love letter she finds a breakup letter… on the most romantic day of the year. A three page, tear stained breakup letter with lines such as “it’s not you, it’s me” and “there are other fish in the sea”.

*Enter overdramatic break up scene and my mother threatening to call him and find out what kind of boy breaks up with a girl on Valentines day. Helloooo high school drama*

I’ve been able to top this dramatic heart wrenching break up with other heart breaking Valentines days though. One ex admitted to cheating on me after one to many glasses of red wine and promises to love each other no matter what….

“Jill, you love me no matter what?”
“Of course, love of my life, what is it?”
“Well, you know last weekend when I told you I had to work late?”

BAM! That one hit me right in the gut! I should have known it was coming… Happy Valentines Day to me!

I haven’t let these heartaches in the past ruin my optimism for future relationships and either should you. Your past relationships shouldn’t ruin your future ones.

Let go of the pain someone may have caused you.
Let go of the guilt if you have caused someone else pain.
Apologize or accept apology and move on!
Life is really, really short and love is really, really important… get out there and find it!

Here is a short list of great events for singles in Chicago this weekend. None of these events are sponsored by, but they all look fun! For more ideas become a member or member!

Some events this weekend for singles in Chicago
Fado’s Irish Pub– Get a free beer if you bring a photo of your ex.
12th annual “Screw Cupid” event
A singles party in River North
Laugh it up!

About last night…

I hosted a Singles “Nuts & Bolt’s” party. As usual I was nervous as could be. It is stressful throwing a party, let alone a party with over 150 guests who all have the same goal and have paid me to help in finding it.

Two of my “cupids” had family emergencies (my heart goes out to both of them) so I was already down on my help, this was only my second event in Chicago since moving back from good ‘ol Tennessee… I forgot my pens… I lost a bag of nuts on the way in… my heels were killing me.  Oh… and it just started snowing HEAVY. After handling these emergencies I finally got the bar set up, tables arranged with mints on the tables, lit the candles and set up the name tags and placed the nuts and bolts out. I was nervous, but I was ready to rock! The remaining cupids showed up, my photographer arrived early and things were looking great. Looks like my bad luck was over and the good luck was starting to roll in because the singles started arriving at 7pm.

 By 7:30 we had about 30 singles ready to mingle. By 8:00 we had close to 100 and at 8:15 we surpassed our RSVP count and were over 150 singles. WOW!!!  The nuts and bolts party was in full swing. You had a 1 in 5 chance of finding a match and everyone was searching for that match. I had bought extra large and extra small bolts and the matching nuts so it’s fun to watch the guy with the TINY bolt trying to make a fit to the lady with the gigantic nut! Always guaranteed for a few laughs. A few of the singles were a bit shy and hung out in the back, just observing but I noticed after about 30 minutes these shy singles were out there shoving their bolts into nuts and nuts into bolt, laughing and cracking up with everyone.

The people:  Talk about a melting pot!  I had Brazilians with sexy accents, cowboys with sexy hats, cougars looking for boy toys, sales executives, lawyers, a  doctor, a veterinarian, two school teachers (both of them were HOT!), sexy ladies in their 40’s and 50’s, three police officers, sexy men in their 40’s and 50’s, a few people in their early 60’s, college girls, a brewery owner,  frat boys, Hispanics, African-Americans, Caucasians, Jewish guys and gals, Catholic guys and gals, a Wiccan, Republicans, Democrats, a lot of 30-39 year olds, a firefighter, a brick layer, two office managers and someone who works for Groupon. I had “matchmaking” form that people filled out; it’s so neat to see how different we all are, but how similar we all are too.

The raffle tickets were a bit of a hassle. Being down two Cupid’s, I had to utilize only one raffle ticket and nuts/bolts exchange station. Trust me, it got crowed. Finding a match is great, but getting a raffle ticket for cash, Victoria’s Secrets presents, gift cards and perfumes can be the icing on the cake… and no one wanted to miss out on this!  I’ll make sure the next event has two raffle stations.

My Cupid, Colleen, mentioned at the end of the night that she saw two people leaving together hand in hand. I received a phone call this morning (a little too early – and you know who you are!) thanking us for the night. She and he went out to grab a bite to eat and to talk a bit more. She says that he walked her back to her car around 1am, gave her a quick kiss goodbye and then sent her an email 30 minutes later saying how great it was to meet her! They have plans for next weekend. I love hearing this. It makes everything worth while.  This love connection wasn’t the only one. I personally saw 3 (THREE!) couples getting close on the dance floor and maybe even swap a kiss at the end of the night (I notice everything!). I wish them the best of luck and tell them to call me if there is a love connection!!!  A few people told me that they exchanged phone numbers and many people told me how much fun it was and how different a Nuts & Bolts party is compared to a typical night out.

About the bar:

Houndstooth Saloon  is one of my favorites. The decor is cute and sexy, the music is great and the drink specials are outstanding. The only problem is all the singles had winter coats, but no coat room. Another issue (my fault) is the bottle neck that happened when you walked in. We had placed the check in tables to close to the entrance and caused a bit of a hold up. Live and learn, right? I thought my cocktail waitress was right on it- even with all these customers she was friendly and sweet. She also kept asking me to find her a date, and I’m going to keep my word and find her someone sweet. I’d love to do more events here in the future.  

Over all, the night was great. I personally met some awesome new friends and made some love connections. More events are coming; I hope to see you at the next one!

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