Tag Archives: advice

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.

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!



She’s 16- he’s 28

Someone, nameless, asked for advice yesterday.

He thinks he’s in love with a 16 year old family friend. Not lust, he pointed out, but love. He’s 28.

 Bits of his e-mail: “I’ve been close to her for a long time, given her advice about love and family and friendship… I know she’s attracted to me to becaus she shows off more and more skin, giggles and flirts with me now…. what should I do? I really love this girl, but don’t want her parents and my parents to hate me. I understand that it is illegal until she is 18, but people can’t help but who they fall in love with right?”

 — My answer:

DON’T be a fool! This girl may be attracted to you and may be showing off and flirting, but she is just practicing on you. Girls at this age have just realized their sexual “power” over men and boy oh boy- she’s got you under her finger. Do you realize what deep shit you’ll be in? If you tell her parents, they will ask her about and no doubt, she’ll deny it and make you look like the asshole. If you really love this girl, you’ll wait to make your move. You’ll deny any advances she may make on you. Do not be alone with her. Wait until she is 18, or better yet 21, then see if there is still love.

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!?