datemeisterlogo.fwThe DateMeister® (Mary Reilly) has dabbled in singles events planning for twenty years when she first joined Match.com in 1996 and reached out to the company and asked if she could host small gatherings in NYC bars for their pioneering members (many of whom were too afraid to even post photos in their online profiles). Ms. Reilly still has the black sweatshirt with the Match.com heart logo on it that the company sent her. Little did anyone know then that Match.com would become the most popular online dating site in the U.S. with both the largest paid user base and an outstanding success rate. “I am a Leo who is driven by my heart; I was never afraid to try new things in my quest—or to facilitate other people finding love”.

A few years later, Mary attended a speed dating event for the first time and approached the two owners afterwards with some marketing and promotional ideas. The owners of NY EasyDates hired her on the spot to be their first event hostess because they were getting burnt out running the events while working full-time jobs. The part-time gig enabled Ms. Reilly to study how singles interact while meeting men herself. Fast forward to 2015, a year after she kicked out her long-term boyfriend of nine years, and Mary is now The DateMeister®, a dating expert, and is co-authoring a book with Dr. Martin Kelly entitled “Date Defensively: How To Know When To Get Off At The Next Exit”. The book will help readers identify the red flags of whether or not their date may be personality disordered and help prevent heartache, abuse or divorce. “I ignored a lot of the warning signs that my ex had Narcissistic Personality Disorder because I wanted it too much”, states Mary Reilly, The DateMeister®.

So why host Cougars and Cubs events instead of just singles parties for people over 40? We live in a society that assumes the worst and is too judgmental; ever since Demi Moore and Ashton Kutcher there have been jokes about younger men seeking money or professional gain, and lonely older women seeking all night sex. “I have interviewed older women and younger men who have met through work, family and friends, or travelling, and the relationship happened because there was a real connection. Many of the women that I spoke to are now in their 60s and 70s and told me that their best relationships and marriages were with men who were ten to twenty years younger”. These women did not “pay to play” but enjoyed partnerships that blossomed, in large part, because neither party was looking for outcomes (e.g., marriage or children). Older women, like The DateMeister® herself (who is 53) are tired of men their own age who either have too little energy or too much baggage or are bitter. Conversely, younger men who are not yet ready to settle down, grow tired of women their own age pressuring them for an engagement ring in the first year or two of dating.

The magic of a mixed-age relationship happens because two people are living in the present and developing real intimacy because they are not focused solely on the future. “It’s really refreshing and liberating,” says Ms. Reilly who has had a few dates and flings with younger men who appreciated her wisdom and were very respectful. Mary tells women over 40 to just lighten up and go out and have fun; no one has to fling—you can just flirt. Since she is mindful that some older women may be embarrassed to attend a Cougars and Cubs event, neither Madame X nor The DateMeister® will be taking photographs of event attendees and posting them on social media.

The DateMeister®’s Debut Cougars and Cubs Party will be held from 6:30 to 9:30 pm on Friday, September 30, 2016 at Madame X Bar and Lounge, 94 West Houston Street (between LaGuardia and Thompson), NYC. Tickets may be purchased at www.thedatemeistercougarsandcubsevent.eventbrite.com. Older women should be 40+ years old and men between the ages of 21-39 years old. In keeping with The DateMeister®’s mission to remain open to all opportunities for love, this will enable women in their early to mid-40s to meet a younger man who may only be a few years younger as well.

Leave a Reply