Tag Archives: dating

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 @ Jill@MingleAround.com 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 www.MingleAround.com 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!


Dating younger men

That hot stud in the office wants to take you out tonight huh?  Some hip new club where the girls wear little more than two inches of fabric and heels 3 miles high? To see a band with a 8 word name that you’ve never heard of?

SHIT! What’s an older gal to do?

“I’m not a cougar.” you tell your best friend “I’m only a few years older than him… cougars wear clothing way to tight and have botox, fake breasts and lip implants, right?”

Your mind races… do you mention that you are probably 8 years older than him? Does he not realize that you are 38… And all you want to do on Friday night is curl up on your couch to watch the Netflix movie that just came in?

 Of course, you are flattered… I mean… normally you get hit on by the 56 year old Fed Ex driver and your friends dorkier friends…. But this is different. It’s fun. It’s exciting. You’ve been (dare I say) flirting with this hot young stud in the office for weeks now. ONLY because you never thought he was an option right?


Girl… every man over 18 and not married is an option! Don’t you forget it!

You’ve flirted with this young hot thing for weeks. Don’t pass it up! Maybe nothing will come of it but a fun night out. Maybe it will end in a long good night kiss. Maybe the night will be pure torture and you fake a migraine and leave early in a cab, but at least you GOT OUT OF THE HOUSE AND MINGLED!

Do you see where I am going with this? Every chance that isn’t going to hurt you, that isn’t morally or ethically wrong, should be taken. Who care’s if he’s a few years younger. Once you’re past that college age, we basically all want the same things. He wouldn’t have asked you out if he didn’t find you attractive and fun. Don’t let the age thing worry you. If he hasn’t asked how old you are, or if your age isn’t public knowledge, then don’t fret. Let him assume you’re 2 years younger. Heck… you spend all that money on anti-wrinkle cream for a reason right!?

I’m here!

I love, love.

That is why I host speed dating events, singles dances and social events for single men and single women. My name is Jill M. Jackson and I’m a hopeless romantic.

  •  I believe in love at first sight.
  • I believe in dating until you find someone who makes your toes curl.
  • I believe that there is someone special for each of us and it is our duty to find them.

My mother and my mother’s mother are both matchmakers. Not professional mind you, in their day and age women didn’t have business cards with that title on it, but it was known. If you wanted a mate for your son or daughter- you called one of them. Growing up I witnessed countless courtings and marriages that started with two people that had the luck of knowing my mom or grandmother.

During high school and college I was the go-to girl. I had a rolodex full of all my single friends photos, names and stats. I’m not shy- if I saw a man that would be great for a friend I’d walk right up and find out if he was single and then hand out her name and number.

Looking forward to posting more in the future about love, dating, relationships, internet dating sites, free dating websites and mine and my friends experiences in dating after divororce, dating with children and just relationships in general.