The “Rules” of Dating


First and foremost – you make your own rules. Only you can decide how a person is allowed to treat you, what you are comfortable doing and when you are comfortable doing it. Whatever you do choose to do – own it. You are your own woman.

The question then becomes – what does that mean? It all used to be so simple. Now, not so much. With the 4th Annual CLE Have A Heart Charity Date Raffle right around the corner, love and dating are all about having fun. To get into the spirit – I’m breaking down the FAQ’s of dating.

Is It Okay For A Woman To Ask A Guy Out?
Typically, I say no. You gotta have him chase you. (Unless you’re at a Date Raffle. Think of a Date Raffle like a Sadie Hawkins Dance. Make a move. Flex your flirt muscles.)

How Many Dates Until You Offer To Pay?
Never. Don’t do that. If you are dating the guy that asks you to pay or go Dutch…there is a serious conversation in your future. It’s not about the check, it’s about how much he values you and your company. Chivalry is not dead. He pays.

How Many Dates Until You Have Sex?
I don’t think there should be a rule on that. If you’re feeling it, go for it. Own it. However, sleeping him on the first date does risk sending him the wrong message if what you’re wanting is not a one night stand. If he doesn’t call you the next day, you probably shouldn’t have done that. Typically, sex and especially blow jobs are boyfriend privileges. Once he commits, girl – you hand it out like candy. Before he calls dibs on you, you are a Big Mac….more where that came from.

One Thing To Never Do On A Date:
Talk about yourself constantly…just too much. Make sure the conversation is a two way street. Guys can’t handle all the chit chat.

The Key To A Man’s Heart Is…
An open oven😉

The Key To A Woman’s Heart Is…
Just tell her she’s cute all the time. (Kidding) Actively listen to and validate her – emotionally, physically. Give her lots of compliments, find ways to let her know you’re picking up on the details…women love that stuff.

How Many Days Should You Wait Before Calling After A Date?
Don’t. He should call you first. And I mean, actually pick up the phone. If he doesn’t, he’s just not that into you…move on.

Guys – Give it about a day. Same day/night is runs the risk of coming off as creepy and the 2 day rule is antiquated. You want her to know you’re into her, right?

The great thing about the CLE Have A Heart Charity Date Raffle? There are no rules! See you all next Thursday, June 23rd, 6:30pm at Barley House in Cleveland. As a thank you for being a loyal reader, use promo code WAGS5 to get $5 OFF your tickets at

How To Be Single This Valentine’s Day

How To Be Single opens on Friday, February 12th and I CAN’T WAIT!


I have had a hard time coming up with something heartfelt (no pun intended) to write about Valentine’s Day. Single or Taken – I’m not a Valentine’s Day girl! Although, bonus! For all of the packed restaurants and overpriced floral items – condoms are half price at your local drug store over Valentine’s Day weekend. Go stock up. You’re welcome.

I do have a certain amount of empathy for the insecurity that comes with those days that seem like they were placed on the calendar just to point out your relationship status. Let me assure you, they’re not. Whether you are lucky in love or perpetually a bridesmaid – I feel like every woman can relate to “How To Be Single“. The struggle is real. We’ve all been there.

Although there’s not much to be found online in terms of spoilers as of yet, after much research I can already tell this flick is the most quotable movie since “He’s Just Not That Into You“. Like life, “How To Be Single” is a comedy. Kind of like that moment that you turn to your girlfriends and ask, “are we on candid camera?” Dakota Johnson, Rebel Wilson, Alison Brie, Leslie Mann and Lily Collins put a voice to every woman’s inner most single-girl thoughts. In a Carrie Bradshaw-esque manner, “How To Be Single” is an anthem for the past or presently single you- that the best parts of you, your character and your life, happen when you give yourself the space to explore the notion that perhaps it is the moments when you’re not in a relationship that define your life.

For a quick girl-power recharge…Check out my Top 8 Favorite Quotes on “How To Be Single“:

8. The Theme Song.

The Trailer starts with Rebel Wilson’s voiceover “I know breaking up sucks – but you know what’s even worse? Missing a night out in New York City.” cue the hook from “Baby I’m worth it” by Fifth Harmony. It’s not just a song, it’s an attitude! Breaking up does suck. Been there. Trade the ice cream therapy for dance therapy and get out there! Cuz baby…you are worth it!

7. “You don’t buy the drinks. Boys buy the drinks.”

My mother taught me this one in college. It’s called “Go in broke – come out drunk”. Sometimes it goes by “flirting” for short. Ever wonder how to start a conversation with a guy? Talk. Smile. Ask him what he’s drinking. When he offers to buy you a drink…say thank you. No, this doesn’t require you to do anything in return. Except be kind and have a good time. Fun is required. Which brings me to…

(Modified move for beginners: Have a mocktail in your hand. For vodka drinkers…go with a cranberry/soda or straight club soda. For ?+coke drinkers…just order a coke. If you are already holding something in your hand all he has to do is ask what you’re drinking…when he does, tell him what you really want. The “tell him what you really want” move may also be applied in other future scenarios. I digress… )

6. “If you’re not having fun when you’re single then you’re not doing it right.”

Nuff said.

5. What’s Your Number?

According to Wilson, “In every male-female friendship there is a total number of drinks – and if you hit that it means that you will definitely have sex.”

I have heard of the whiskey test, but this is new – makes so much sense! What’s your number?

Whatever your number, Wilson also teaches us that Pedialyte doubles as a cure for hangovers. Thanks Rebel!

4. Don’t Fall For Someone’s Looks Alone

Chemistry is most definitely important. The movie’s official Facebook page has a great quote about why it is important to not fall for someone based on looks alone.

How To Be Single” star Brie warned everyone who is currently looking for a relationship that it is a good idea to avoid falling in love with those who have a “fake smile” on their faces.

3. Love Is Not The Enemy

It is important to be happy if you’re single, but that doesn’t mean being in love is always a bad thing. Love isn’t a bad thing. Love is a leap. You have to be inspired to jump.

Collins pointed out that “love between us is better than being single.”

Her words are an important reminder to everyone who is currently navigating the wonderful world of dating that love is not the enemy.

2. Relationships Are Fun

The final “How To Be Single” quote is from Wilson, who said “let’s be honest-I love relationships!”

Although being single and hanging out with friends is a perfectly valid choice, there is also nothing wrong with wanting to have a boyfriend or girlfriend either.

1. “The thing about being single is – you should cherish it.”

Cherish the nights when nobody’s around to witness your single girl habits; The things you do when no one is looking. Cherish that precious time when you make your own rules, watch what you want on TV without compromise and dance to your own beat. Timing is everything. So, while you’re looking for the one to inspire you to make that leap of faith in love – become the person you would make that leap for. Don’t be shy.

On that note, and just for fun… take a page out of Dakota Johnson and Leslie Mann’s book – during a recent interview for HOW TO BE SINGLE, they hilariously hit on former Cleveland heartthrob and 2013 Have A Heart Bachelor Chris Van Vliet from WSVN in Miami.

Try this line on for size: “Can you take off your shirt?”

Have a question? Want to tell me your dating story? Email me!

New Year. New You.


I love this time of year. There’s something magical about it. Maybe it’s the lights or the next-level kindness that seems to pour out of people. It’s sometimes hard to spot this beauty in human kind the other 11 months of year; It’s there. December though…December is like karma-recharge month.

December also holds the record for the highest suicide rate. Why would that be? Some might argue it’s Aunt Elsie’s Fruit Cake. (Still don’t understand why they still sell that stuff!) Let me ask you this – as you are sitting there on your sofa promising yourself you’re going to lose 15 lbs. in 2016, quit smoking & drink less, land that great job, call your parents more often, take that dream vacation and make the next move in your love life – are you happy?

I’m guessing 90% of you took a pause. “Fine” is the Midwestern response to just about everything. But really – do you live with a smile on your face more times than not? When you wake up, what makes you excited to start the day?

Most people live life with a checklist – New Year’s Eve being the beacon of reflection on this checklist. Success and happiness are often defined by how many boxes we are able to check off the list, and therefore how reality matches up to the plan.

As someone who has an app on her phone dedicated to managing checklists, take it from me. If you spend all your time waiting on a job or The One, you waste a perfectly good chance to be happy. Life is short and while having goals is good, 5 year plans are kinda bullshit. Single or taken, working or not, never wait for anything outside of yourself to change before you choose to be happy.

Make that choice now, if you haven’t already. The past is the past. Trying to predict the future will drive you crazy. It’s now that counts. Bonus: Happy is like gravity. You can fight against it, but it exists;  it’s always there. So, choose to be happy and all the rest, with a little elbow grease, will be drawn to you. I promise.

New Year’s Resolution -> Kiss the new you at midnight.

See you in 2016!
Your Cleveland Matchmaker

Have a question? Want to tell me your dating story? Email me!

Cuffing Season



Tis the season for pumpkin spice lattes, Christmas Ale, and cuffing…apparently. I just learned this term. If you’re as out of the loop as I am, “Cuffing Season” is defined as:

“During the Fall and Winter months people who would normally rather be single or promiscuous find themselves along with the rest of the world desiring to be ‘cuffed’ or tied down by a serious relationship. The cold weather and prolonged indoor activity causes singles to become lonely and desperate to be cuffed.”

Thank you Urban Dictionary!

So, why the sudden interest in “cuffing”? No, I’m not feeling the itch. My seasonal allergies do not include an irrational need to join Tinder. Though it is becoming progressively more awkward to maintain my “Rosie the Riveter”-like exuberance about living the single life when ALL of my (formerly single) friends are going two-by-two into coupledom like the next great flood is coming. What can I say? I love my life. It’s gonna take something undeniably special to change my single status. (Fast Fact: Love should add to who you are and enhance your happiness; not be used to make you happy or to define you. More on that next time.)

To these recently cuffed lovebirds….congratulations! Now, you get to ride out the cold Mid-western winter months curled up next to someone. Fast Fact: According to Facebook’s Data Science Team – The November through March stretch kills about two-thirds of relationships. Facebook’s data science team also did some deeper research on the duration of Facebook relationships. “About half of all Facebook relationships that have survived three months are likely to survive to four years or longer,” writes Bogdan State of the Facebook Data Science team. State also reveals the top season for breakups, the summer months from May to July. So, how do you set yourself up for the best possible shot at success? Well, let me offer a few thoughts…


Is s/he your gf/bf? I’m not talking about what you call this person in your inner most thoughts, to your friends or in your diary. Has someone spoken words that resemble titles and commitment? If not, there is no reason you two should be spending the Holidays together. NYE? Maybe. I’m a big fan of the midnight kiss.

During the Steve Harvey TV shoot – I found myself coaching a Bachelor named Danny*. Danny* is tall, has bright blue eyes, dirty blonde hair, super social, has a great job and a lot going for him. Bonus, he has an awesome relationship with his family! Sounds like the total package, right? Well, with a big backyard and a bigger family, every summer weekend is spent around the grill with family, friends…everyone is welcome. Everyone. Oftentimes, he would bring a date. The logic? “The more the merrier.” Then, “all of a sudden” these women would go from cool to crazy clingy. This baffled him. Was it like some kind of internal clock? (Insert a round of gaffaws from the bachelor gallery)

Maslow's Hierarchy of Needs As It Applies To Relationships

If you ever studied Maslow’s hierarchy of needs in college, meeting the parents is at the top of what Maslow called the most fundamental “deficiency needs”. What Danny* was doing without even realizing it, was communicating to these women on a basic level, whether or not there was ever a conversation that he was “in”….all the way. With every introduction to every friend, every family member she was waiting to hear him introduce her as his girlfriend. She was already meeting his parents, how could she not be? It didn’t make sense. And when she didn’t hear it? “Actions speak louder than words” she would say to herself, rationalizing Danny’s* behavior. This doesn’t make her crazy, by the way. This makes Danny* confusing. And if by any chance you (yes…you…the one reading this) do this and you know what you’re doing and choose to do it anyway, it makes you a jerk. My advice to Danny*? Simple. Hold off on partying with the parents until you’re ready to call her your girlfriend. If she or he is not the one you see a future with – the one you think of when making decisions, whose opinion you rely on regularly and whose company you enjoy most night and weekends – just say no to the parent intro.

For those of you that are without a doubt at the commitment stage – you know who you are. You enjoy each other, are confident in where your relationship is going, and see no rush in getting there. You make each other better versions of yourselves. You’re ready to meet the parents. Now the big question – how? Does s/he do the big intro during the Holidays? That’s a lot of family. Go out to dinner maybe?


The Holidays can be a hard time to meet the parents. It’s a requirement to not just like his or her family, but also his or her mother’s cooking. EEK! Bottom line is how this is going to work for you and your SO. Nobody should feel pressured to be part of a celebration that they are not ready for. Maybe a smaller meet-up with just your parents is more your SO’s style and save the big family meeting for July 4th? Cool. Your role is to respect the wishes of your partner. Listen. Then respond. We sometimes skip that whole listening thing and then wonder why things didn’t go our way. It’s kind of important. So is making clear what is important to you. If Christmakah dinner with your family is important to you – say so. Also, be okay if s/he’s not ready for that. Listen. Hear him or her out. And then go be happy with your family without resentment. Don’t be a sponge. Let it go!

Celebrating together can be awesome but only if both players are participating of their own volition. Ultimately, the best thing you can do is to set every one up for success. More times than not, parents are going to want to protect their kids…Daddy’s always protect their little girls and no mother on earth thinks there is a woman who is good enough for her baby boy. Disarm them and set your SO up for success and you can’t go wrong. It’s easier than you think.

1. Avoid sit-down restaurants if at all possible. Unless you come from a family of “fancy-pants” or there is an emotional attachment to a spot (For example: your dad and your SO have the same favorite spot), take the formality out of it. Emotions are going to be running high anyway, no need to add to it. Distract! Distract!

2. Highlight your SO’s strengths. Let your parents see the best of him or her. You like is person for a reason. Pick a setting that will show this off. Do you guys like bowling? Suggest a night at the 4th Street Corner Alley for Bowling. Drinks and food can be delivered to your lane. By the end of the night, if all goes well, it’ll be a Battle of the Sexes with the Ladies playing on the same team and the Gents on the other. Ultimately, most parents want to make sure that the person in your life first and foremost treats you well.

My personal favorite idea – have a dinner party at your place! Invite the parents over to your place (neutral territory) omitting holidays! Extend the invite as if it were your SO’s idea. “{Name} and I were talking and s/he would really like to cook dinner for you both in the next couple weeks. We were thinking my place. Whatever is convenient for you.” Double Bonus – This is especially good if your SO has kitchen skills! When people are nervous…it’s natural to want to keep your hands busy. Your SO gets to be social, look smooth, and make the best kind of first impression – seen actively catering to the crowd and caring for their son/daughter.

Bottom line – when it comes to tackling the holidays, single or taken, stay cool. The holidays are only “a thing” if you make them “a thing”. Not having that plus one at the dinner table is not the end of the world. Just do you. Don’t fall to the peer pressure pitfall. Don’t worry what the calendar says. Or your mother. A false start is a sure fire way to go from cuffed to cat-lady before Christmas. Remember, relationship building is a marathon…not a sprint.

*Names have been changed to protect the flawed and the fabulous.

Have a question? Want to tell me your dating story? Email me!

That Thing Called Love

Welcome to my Cleveland Matchmaker blog! I am equal parts nervous and excited to begin this adventure…grateful to my friends and family for the push to start this chronicle and to you for reading. Cleveland’s singles scene is unlike any other…it’s HUGE! And can more times than not, feel like a labyrinth. My hope is that both men and women will have a few laughs at my expense, gain some wisdom from my weaknesses, break some bad habits, and get excited about love and dating! Because let’s face it…if you’re not having fun, you’re doing it wrong. Writing is something that I have wanted to do for a long time and that friends and followers of the Cleveland Have A Heart Charity Date Events have asked me to do…so here goes nothing!

Why “The Cleveland Matchmaker”? Why should anyone care what I have to say about Love, Dating & Relationships? That’s something I’ve thought a lot about. No, I am not Patti Stanger. I cannot say that I am directly responsible for anyone’s happy ending…or rather, happy “new beginning”. Well, maybe one…we did have one Bachelor “put a ring on it” and find happily ever after less than a year after meeting his MRS at our second annual CLE Have A Heart Charity Date Raffle. I am a great listener. The dating dance…behavior and relationships have always fascinated me. More often than not, the most important part of a conversation is listening…listening to what is being said and to what isn’t being said. I am also a big believer in answering when opportunity knocks. The Cleveland Have A Heart Charity Date Raffle started as a joke. Yes, a joke. Four years ago, and after about a dozen humorously bad blind dates (we’ll get into those later) within a 3 month period, a post-breakup/rebounding me found herself having sushi with a couple girlfriends. My friend, Liz, was aghast at the stories of my experience and proposed hosting a Bachelorette-Style fundraiser…she would pre-screen 25 single men, and the winner of this dating-contest would win a date with me! All proceeds to benefit the charity of my choice! I turned 50 shades of RED! Since that day my team and I have hosted 3 Date Raffles (I have never been a contestant) and numerous mixers resulting in countless dates, over a dozen long-term relationships, and the one aforementioned marriage.

I have been called many things in my lifetime…the PG-stuff?: “too nice”, “too blunt”. It wasn’t until a few weeks ago when the producers of The Steve Harvey TV Show found me and asked that I help field produce a Cleveland Dating segment for their national show and asked was I ever called “The Cleveland Matchmaker”. No joke. I was floored.

What happened after that call was 5 days of surrealism that included location scouting and recruiting/date-coaching bachelors for one woman who claimed she “couldn’t meet a good man in Cleveland”. Let’s just say, we proved her wrong. See how that all worked out here:

Stay tuned…I have no idea what I’m writing about next except, well…life! I have decided to write about anything and everything that is on my mind about dating and daring to find love in Cleveland at a given time. If I am sent a question or am able to help someone in my everyday life, I hope to share that story with all of you. I hope to have some guest writers as well. Get the guy’s perspective.

So, are you ready for that thing called love? Here’s to taking off on a crazy adventure…hopefully you’ll come along for the ride!!!!!