Category Archives: life as a matchmaker

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!




About last nights “CaffeineDating” event

I had the pleasure of hosting a speed dating event on Friday night with 22 of Chicago’s finest singles over 40. What makes this event unique is the fact it truly was “speed” dating… we were all hopped up on caffeine instead of liquor!

No offense to liquor, I do enjoy a glass of wine with dinner  or shot of tequilla on the weekend, but sometimes it’s nice to change the scenery. Argo Tea partnered with us and allowed us to use the private space upstairs from the Tea Cafe on 1 North Dearborn. This room had a pretty amazing view (okay, not amazing…we were only one story up…but it was a nice view with huge floor to ceiling windows!) and had the smell of teas and coffee tickling our noses.

Disaster #1… What room?

Upon my arrival I searched for the manager with whom I booked the room and scheduled catering with. He was no where in sight and my private room was full of students. I also was getting nervous because I was not seeing my catered foods and drinks…. uh ohh.

I’m thinking, “Did I book the wrong day? Did they forget my event? When is everyone going to show up? Why is the room so hot?”

I grabbed the barista from the cafe and asked her when my room would be set up and she looked at me blankly and said,”What event?”

“Ha! You’re kidding right? What room! Funny! Who set you up to this?” was my response.

She then explained that the manager who I’ve been working with all month was actually not with the company as of this morning…. WHAT!?

BUT, Argo Tea was super awesome and lickety split got my room set up and offered the daters complimentary food and great beverages from the cafe. It worked out well for us… just started out as an event planners worst nightmare!

Disaster #1 fixed.

Disaster #2… Too many men…

Speed Dating is a difficult event to keep the ratio of men to women even. No matter how hard I try something always happens. This particular event was booked even 11 men, 11 women. Then the day of THREE women called to cancel due to work or family issues. Three?! Come on, cut me a break here! I can’t have too many men, especially three men too many!

So, I post some quick ads on Facebook and twitter and get three great gals to fill the spot (I had a waiting list for the event, so filling the spots wasn’t a problem).  Great, back to even. Easy….or so I thought!

One male paid and didn’t show up, and another female showed up at the door with confirmation but I hadn’t had her name on my email list. (Website bug… fixed). So, I started out with too many men, now I have two women to many. Which I think actually worked out fine as we had 10 men and 12 women. The women had two rounds of “No date” which gave them time to freshen up in the washroom, text their best friend (hopefully telling them to come to a Mingle Around event!) or refill their beverage.

disaster #2…. fixed, but reversed!

Disaster # 3…. Is it hot in here?

I’m a nervous gal. Mingle Around is my baby and I’ve got my name all over it. If it fails, I fail. Hence, I get nervous before events because I want everyone to have a good time and positively speak to other single friends about Mingle (hopefully a 5 star Yelp! review too). So when I was sweating upstairs dealing with “disasters” I thought it was just me. It wasn’t. It turns out I was fine, the room was just hot. Like really hot. We’ll have that fixed for the next upcoming “CaffeineDating” event, I think the new manager just didn’t have the key yet for the heat control. So if you were at the event and sweating due to nerves, no one would know!

Disaster #3 not fixed, but could have worked in your advantage!

That’s it for the disasters.

The event actually ROCKED. About an 90 minutes of “mingling” and a 90% mutual match rate for our singles. The speed dating had a great crowd of attractive singles over 40 who really were personable and fun. Most of the speed daters hadn’t actually been to a speed dating event before, so it was a new concept for a lot. I sure hope they had a great time. I’ve received a few thank you emails the day after, I’ve attached a photo of one. The thank you emails are my absolute favorite thing about this job…. it’s wonderful doing something that people love!

Upcoming CaffeineDating Event- For singles in their 20’s and 30’s. Friday November 26

Other upcoming events

Thank you letter

Thank you letter

ABC came to film our singles party! (Nuts & Bolts Party)

The true story on how Mingle Around gets on ABC news— for hosting singles events.

I manage a restaurant, anyone who knows restaurant life knows not to call during lunch or dinner hours. Yesterday (thursday) I received a phone call from a strange 312 number that I ignore because it was the lunch rush and I was busy attending to 300 customers.  I didn’t wind up checking that voice mail until about 4:30 pm and had to listen about 4 times just to make sure that I heard right. “Hello Jill, this is ABC calling and we’d like to do a story on your Nuts & Bolts singles parties. Please call us back at 312-555-5555.”

HA! Yeah… which one of you pranked me? That’s all I could think of. I figured it was a joke until I checked my e-mail and an email was sitting in my unread box.

WTF!? is now all I could think. What would ABC want from me? Yeah, the parties I throw are fun. They do attract a diverse and amazing crowd, but it’s not like I’m throwing parties at the Hilton or inviting celebrities. I’m a normal girl average girl and Mingle Around is my baby- but it’s not making anyone a millionaire. Doesn’t ABC want really intense and exciting topics? Then I got to thinking that maybe I underestimate myself, my company and the potential (and current success) that it has.

So, I call back the producer and he asked me so kindly if he could bother me by coming out to our singles event on Friday night. Ha! Like I’d say no to that! I agree, thank him as professionally as I could, tried to act cool, like news stations call me everyday and as soon as he hung up I screamed and started a little dance in my kitchen!

I danced for a minute, enjoying the random good luck that was just bestowed on me and then I started to freak out. What should I wear? How can I lose 10 pounds in a day? Am I tan? Should I get my nails done? What will I say? Will I have a good and packed crowd? What if I stutter or sweat? What if I look like an idiot? What if….

The night was short and I needed to find an appropriate dress, shoes, makeup, accessories and all those fun girl things. I mean, I’m going on camera those precious 10 seconds of fame went straight to my head for a few minutes and I was ready to whip out all the credit cards.

Anyone who knows me, knows that I’m not “stylish”. I’m from the country, love to get dirty and don’t mind if I break a nail. Don’t get me wrong, I LOVE to dress up, but I usually take my sister with to help find outfits…. because to me, a too tight red mini skirt with leopard tights and a pink sweater would look hot. (yikes, someone call “What Not to Wear”!) I knew that wouldn’t work for television… I needed to dress the part.

Thankfully, a fellow matchmaker (Stef in the City) saw my excited tweets and contacted me. Gave me some great TV advise that I took her up on and I found a cute dress, shoes and accessories all downtown and on sale!

The event started at 7pm and the news reporters were there at 7:15 with a giant camera. Eeeks! They set up a great shot in the back room, sat me down and interviewed me. Of course I screwed up my words and when I spoke about nuts and bolts I said it backwards… “Girls get a BOLT and Guys get a Nut” (duh… wrong!) so I had a lot of do overs. The producer was so nice though… he even told me I was sweating too much and advised me to wear a jacket . So gross and embarrassing… girls shouldn’t say things like that, right?! I’m just keeping it real! You can’t blame me, there was a giant, hot spot light on me, a giant camera and two strangers interviewing me with a crowd of Mingle Members watching, who wouldnt’ be sweating!? I felt confident at the end of the interview, I think that I pulled it off .

After my little interview, ABC news interviewed a few Mingle Members about their experiences dating and then they took a few shots of the party. Around 8pm they took off and I could finally relax and enjoy the event!

This event was all ages, but the majority were 28-38 range. There were some  *really* attractive girls and guys here tonight and everyone seemed so nice! A lot of networking, some new friendships budding and two couples really kicked it off, while at least six more seemed to have some major potential. It seemed that almost every guy left with a few new phone numbers in his phone and every girl seemed happy for some great potential dates!

Ahhhh… it was a great night. So many new faces tonight and I love when people let me know what a great time they had, and how different a “Nuts  & Bolts” party is from any other night out. It’s just so easy to meet people and so much fun.

I can go to bed happy tonight, knowing that I threw a great party, there are a couple of potential couples, ABC knows who Mingle Around is and that I have such an amazing group of Mingle Members and friends.

The only worry I have, is for Sunday night when they air the little interview… please don’t look like an idiot Jill!



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.

About last night (10/14)

I host singles events in Chicago and after most events, I’ll blog a few thoughts about the night from both a matchmakers point of view and as a new small business owner.

Last night was a young professional’s singles mixer with at “Nuts & Bolts” theme as an icebreaker. I also had two singles on a first blind date, professionally matched by me. A lot was happening and that’s the way I love it! I was nervous about the blind date for my two single friends, and I was nervous that the party wouldn’t be as much of a success as it was. I had  no reason to fear- as the party was AMAZING and the blind daters are both very happy with each other.

48 sexy singles had RSVP’d and almost everyone showed up plus a few singles from the bar next door. I love when that happens- people peek into our private room and they get interested and started mingling with us!

The first two singles that walked in the door were very attractive smart girls who are brand new to Chicago. Without knowing anyone in this big city, they say it makes meeting people even more difficult and I understand. Both ladies approached me at the end of the night to thank me for hosting the party. Both ladies had met a few potential dates and had a bunch of new numbers in their smart phones.

Interesting turn of events, I had a (competing) professional matchmaker show up at my event and introduce herself to me. She and I had a chance to chat for a bit and she seemed like a sweet girl. I’m always flattered when other Chicago matchmakers ask me for advice or to discuss partnering up. This is the third time I’ve had other Chicago area matchmakers attend my events to either meet me or “scout out” the competition. It’s always a strange feeling knowing that your competition is watching every move you make, but it keeps you on your toes!

Speaking of competition, I had the chance to meet Ben Shimon- who runs S3 leagues– a singles sports league team in Chicago. He came out last night to introduce himself, meet some ladies and to hand out flyers for his upcoming fall/winter bowling, volleyball and whirlyball leagues. We had spoke earlier in the week about cross promoting and hit it off well over the phone. Though we both cater to singles in Chicago- we have different products, so working together seems smart. I’m glad he came out and am looking forward to working together with him on some large events in the future. Quick promo spot- Check out his website and join a league for the winter!

I must be starting to “come into my own” as everyday I’m receiving emails or phone calls from potential sponsors, partners and interested parties. It’s nice that after so long I’m starting to get to where I want to be. Hopefully by this time next year I’ll be able to focus 100% of my time on Mingle Around and produce amazing events every night of the week. My “day” job is great, but people always say the way to true happiness is to do what you love. I love Mingle and am excited to do what I love.

Back to the party! The party itself was great. There were a good mixture of singles and it’s always fun watching the natural interactions between people. Mixer events are truly one of the best ways to meet someone and events with an icebreaker (such as nuts & bolts matching) only help to facilitate the natural progression of mingling. When you have a superficial goal such as earning raffle tickets for prizes- you have a natural out of conversations that you don’t want to be in AND a natural reason to speak to attractive or interesting singles. Unlike online dating- you actually get to feel a real connection with potential mates and you save time when there isn’t one. Photos from singles event here!

As always there were a few “fails”.

 Fail #1. “The girl or guy who can’t hold her liquor”
Repeat after me: “Too much liquor makes you sicker”. When you’re the girl falling off of bar stools while asking to take someone home, you’ve probably had too much. If you’re the guy saying yes to the girl- you are either an asshole or a predator. Now, thankfully- this did not happen at the Mingle Around party last night, but I watched it happen at the bar after the event was over. I’m the one who caught her falling off of the bar stool. When I asked her if she wanted me to catch her a cab and to walk her out of the bar- the jerk of a guy she was talking with pushed me away and told me he’d be taking care of her. Of course he told me this with a wink. Really. A wink that said “Yes, I know this girl if drunk as a skunk, and I know you know… but yes, I’m still going to take her home and do all types of wrong things to her.”

Fail #2 “I forgot my shoes”
It’s happened before and will probably happen again, but I left my house in “house slippers” instead of my black heels. I hate heels and only wear them when necessary- so I had worn my glittery flats while dressing and to catch a cab. I had thought that I packed my black heels with my nuts & bolts party box, but had forgotten them by my front door. I’m not uspet, my house slippers are cool- gold sparkles and all, but it just goes to show that I really would forget my head if it wasn’t attached (though, it was nice to wake up this morning without aching feet!).
That’s it for fails, and I had to really stretch to find something. It truly was an amazing night.

I hope you can make it out to the next event we host and help make the night even more spectacular. Singles event can be found on our website

Have a great weekend everyone!


Thoughts about last night

Just in case you stumbled onto my blog, I’m a matchmaker and owner of My cupids and I host singles parties in and around Chicago and I update my blog with the good, the bad and the ugly. I’m a huge believer in love and in honesty. When a party or matchmaking event goes good, bad or funny, you’ll be the first to know. On to the story…..

I’ll be honest. I was really, really, really worried about hosting last night’s singles party for singles aged 35+. For one, I had it on a weekday night instead of my typical Friday or Saturday. Secondly, the party I threw two weeks ago (on Bears preseason opener) had a low turn out (though great guest list). Thirdly, it was my first singles party for just an “older” crowd. Typically I mix my crowds up with all ages.

It turns out that I had nothing to worry about as 90% of my RSVP list showed with a few more people showing up to purchase tickets at the door. (For anyone who has ever thrown a party- you know the pain of the RSVP’er who never shows up. With singles events this pain is triple as many singles purchase the tickets and then the day of, they chicken out and become a no call-no show. Being a matchmaker and focusing on having a fairly even number of compatible men to women at these parties is very important so when the RSVP’er doesn’t show it can ruin the dynamics of the entire night.)

The party started slow and one of my cupids whispered in my ear “it’s like an 8th grade dance in here”, which was so true. Gals were sitting at tables talking amongst each other and the  guys were at the bar looking slightly nervous but ignoring the situation. I knew I had to get things going. Thankfully for me I have some of the best cupids in town who are able to get into the crowd and liven things up.

Once we got the party rolling it all went smooth. The crowd was great with less dirty jokes than I expected and much more conversation than I’m used to. You see, typically these parties get people all riled up to “win prizes”. Everytime you find a matching nut or bolt you receive a raffle ticket. At the past few parties, I felt as if the crowd was more interested in raffle tickets than meeting matches but at this party I was pleasantly surprised at the amount of conversation that was happening.

Two couples last night left earlier together in the evening to grab cocktails away from the crowd and I’m hoping to hear positive things about their evening soon. Another couple left together at the end of the night, the man was being a true gentlemen and walking her to her car. I saw them exchange phone numbers and on their way out she looked back at me over her shoulder and mouthed “thank you!”. I am still smiling over this.

On a personal note I had a realization that people actually read these blogs and my facebook page. Maybe you (the reader) don’t realize this, but when I’m siting at home as I am now, drinking coffee and typing away, I often feel as if it’s in vain and that no one reads or cares that I’m trying to both make something of myself and to more importantly help all of us find love. But I’m wrong.

For example, I was approached last night by a man who thanked me for being his facebook friend and for writing these silly blogs. He’s been following and reading for a YEAR now, but had never had the courage to come out to an event. Now, this man was not shy or pathetic, he was well-educated with a great job. He was able to easily keep conversations with the ladies going and he was also easy on the eyes! He had just never been to a singles party. He was not finding high-caliber women at the “conventional” locations so thought he’d try it out. He told me that reading these blogs and seeing what happens here really made him feel comfortable with the idea of coming. I LOVE this feedback! He wound up making some new friends, but not a love connection last night…. but I feel that he’ll be back again soon.

Well, that’s all folks. I’ve gotta run- two matchmaking clients to meet today as well as my “9-5”.  I have a few more events for September in the making and hope to meet you all soon!


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…

Happy Mothers Day.

The day started out well enough. It’s a beautiful mothers day Sunday, I called my mom to say “Happy Mothers Day” and to ask if she received my gift yet. When I asked about her gift, she states that  all she wants is a grandchild. Ohhh, woe is her to have three daughters in their child-bearing years and not a baby shower in sight.

 “Jill, just settle down and get married already… you know what happens to women who are single in their 30’s right?”

“No, mom… please indulge me on your special day. I’d love to know what will happen in 87 days when I turn 30.”

“You know very well what happens, your child-bearing years are coming to an end, men start looking at younger women. You’re the matchmaker you should know this by now. It’s time to get serious about getting married… before nobody wants you.”

“Jeez, thanks Mom.”

I understand that she is ready to be a grandmother, but I’m not yet ready to be a mother. I’ve still got a few more years of frolicking up my sleeve and am not convinced that life is over as a 30 year old unmarried woman. I constantly match women in their 30’s and beyond with men who are crazy about them. Age ain’t nothing but a number… just don’t tell my mother!

Happy mothers day Mom. I promise you’ll have a grand baby you can spoil someday… will a grandpuppy work in the meantime?! Thank you for teaching me everything I know about love, life and relationships. And no, turning 30 in 2011 is not like turning 30 in 1980…. we’ve got plenty of time to figure it all out!

To all my single mothers out there, XOXO. Happy Mothers Day!

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