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March Is the Month for Long Shots in Dating

By Andrea McGinty March 26, 2024 Dating

Dating? Ok, just go with me here. Stay with me. This is about dating. I’m a sports fan – I hit Spring Training on Sunday in Florida with the Red Sox and Yankees and watched my team wipe out the opponent. And now I’m caught up in March Madness and was glued to multiple channels a few nights ago. And saw some things that reminded me of dating. (After over 25 years of being a dating coach, I can compare any sport to dating… you’ll probably hear me write soon about my idol Messi and comparing soccer to dating).

Is online dating a long shot? I don’t think so.

As I watched long odds Oakland University from Michigan (who?) take down #3 seed Kentucky, I thought of all those fairy tales… in dating and sports. Remember when the Red Sox were down 3 games to nothing in the World Series and came back to win the next 4?

So, How Is This Similar to Dating?

Reaching for the Long Shot

It’s tempting to always date the same type (same look, same ethnicity, same job, etc.) as you have in the past but those long shots (different ethnicity, look, hobbies, career) can sometimes pay off in a huge way.

The upset/the surprise. Maybe you didn’t find your Prince Charming in the first round, but the dance is just beginning.

Listen To Your Dating Coach – Not Your Friends

Oakland walked on the court knowing public opinion was against them, but it didn’t stop these men. The Oakland coach has been there for 40 years – and finally scored. And then I have clients who after two weeks on an online app or dating site want to throw in the towel – when the magic could be right around the corner. 40 years! Hey, you can meet someone in 3-6 months online with the right strategy.

Attitude Matters

Positive attitudes can take you all the way to the final four… or more. I can tell when I talk to a new client on the phone what their odds are most of the time – so much comes from their mindset. And, if they don’t have that, I do my darndest to change their attitude.

Steve, a client of mine in Los Angeles, in his 60s, generally dated the LA stereotype model, aspiring actress, etc. I found a pretty nurse and he said, no way’’. But I’m pretty convincing and said, “What the heck, Steve? It’s only a date.” Vanessa (the nurse) and Steve just got back from a trip to Seville, Spain, and he called to ask me if it was too soon to propose. Oh, happy day for me. (and Steve).

Only Making Safe Bets? Time to Go Out on the Ledge

Janet, 61, an NYC client was only dating the Wall Street types. She was also married to one. While looking through potential dates online, I saw Mark, a fireman/stand-up comedian, and she said I was crazy. But I liked his midwestern values and his sense of humor. Janet is super witty with an infectious laugh.

“Try him,” I said. His profile was well-written, down-to-earth, humble, and sincere. He was adorable from what I could see on paper. Janet texted to thank me this week, and said she’d never laughed so hard in her life or felt warm butterflies each time she saw him. Date 5 coming up Saturday. Long shot yes. But what did she have to lose except an hour of her time?

You Don’t Quit in the First Round

Sometimes it’s a windy road with unexpected surprises. Month one online she might not have been there – and suddenly new people pop up in week 5 or week 7.

You pick an underdog as your boyfriend or girlfriend – chances are they are going to work harder for your trust and love. Nobody wants a cocky ball hog.

My Own Story

Last night, Jeff (my fiancée who I met over a year ago online) told me I was Kentucky and he was Oakland. The underdog. No, I disagree – he’s not the underdog but he’s definitely not the stereotype I looked for online. But when I read his profile, I sent him a message.

Other men that I reached out to always commented on looks or what I did professionally. Not this guy. His message back to me read, “You know why I’d like to have lunch with you? Not because you’ve sold multiple companies but that you host Thanksgiving for 40 people each year and do all the cooking. That’s pretty amazing.”

I sort of fell in love with that message as family and friends are my number one priority. And he was a hundred to one shot. He was my 2023 FAU. (The surprise team from last year who I ranked high in my betting pools this year.)

I like long shots. Many things I have done career-wise and in life have been long shots.

Take a chance. You could be Oakland and find that person of your dreams.

Let’s Have a Conversation:

Do you like long shots – in sports and dating? Have you adopted a “can do” and “I beat the odds” attitude or do you give up easily? What do you expect from online dating and are you ready to do things a bit differently?

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I was married to a white collar kind of guy. Got it in my head that I need someone who is college education, had a good paying job and would be the provider. Fast forward to my divorce almost 20 years ago and I met two wonderful guys who didn’t have the same education nor were they “professionals”. The first one died unexpectedly four years into the relationship and the other one I’m still with after 12 years now. He’s my husband – retired – but when I first met him his job was a construction worker. At that point, when looking to date, I didn’t care whether the guy was a white collar or blue collar kind of guy.


Randi—great share. It’s funny—my latest engagement this week is a well-educated attorney and he is in the construction business too. They are a lovely couple.

Stephanie Bryant

I have to have an attraction initially. It seems you are a dating coach and a matchmaker. I probably would be successful too If I had one, I don’t have the money.


Yes, Stephanie, I agree you have to have attraction—though I’ve learned in my 30 years of doing this that it can happen on Date #2 or Date #3—sometimes it’s not the first date. I’ve had male clients tell me—“She was fine but by the second date I thought she was beautiful”. So much is personality and attitude. As my client who just got engaged said to me when she signed up with me “Oh, I can’t take my money with me and I’d rather have a life partner so this is my investment in love”.


I agree. It took several dates with my husband before I became attracted to him. He’s not the greatest looking guy…..I’ve dated some others who were better looking than him but other things make me attracted to him.

The Author

Andrea McGinty is the founder of It’s Just Lunch dating service. She sold it and founded so she could help singles navigating online dating. In the 2020s, she knows the best way to meet people is through online dating using a professional coach and specializes in singles in their 50s-70s!

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