Maggie O'Brien-Pappalardo

Contract Matchmaker

A seasoned date coach and Matchmaker, Maggie has written and shared her dating advice in many articles and blog posts. Maggie is a true dating expert - she is passionate about supporting her clients through any dating challenges and helping them to achieve their goals.

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A Matchmaking Expert

Maggie easily connects with everyone she meets. She brings enthusiasm to the dating journey and supports her clients through their entire experience. Maggie's goal is for each client to approach relationships with confidence, optimism, excitement and grow to the best version of themselves.

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Your Personal Wingwoman

Truly thoughtful, Maggie reminds her clients that everyone’s journey to love is different and encourages individuality and growth throughout the process!

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Featured In

Matchmaking is emerging as a niche antidote to the agonies of online dating Read More
After I committed to the process, I felt enormous relief. I no longer had to fret about optimizing my chances of meeting eligible bachelors. Read More
A personalized, premium experience where you get a partner throughout the entire process. Read More
A lot of men come to us asking, ‘What’s behind the door of a yoga studio? Where are these amazing women hiding?' They love the idea that someone else can do the legwork. Read More
We're all so f*ing busy. We do need efficiency, it's a lot. Other than dating apps what do you do? Go to Three Day Rule. Read More

Hear From Our Members & Matches

The women I met were lovely, successful, and refined! My last match Christine is beyond a dream come true, because I never would have dared to dream of a woman like her... And I never would have met her if it wasn’t for Three Day Rule!

Chris, 54

Thanks Three Day Rule, I’ve met a man who has swept me off my feet. She listened to what I was looking for in a man when I didn't know Chris even existed. I am so grateful Three Day Rule came into my life - they truly know what they are doing!

Christine, 31

I am beyond impressed with the professionalism and quality of Three Day Rule. Not only did the man I meet through Three Day Rule impress me with the quality of the personnel that Three Day Rule interacts with, but Three Day Rule helped me to find my soulmate.

Daia, 33