Do you know that friend whose advice is always spot-on, even if it’s not what you want to hear?

It’s me. I’m that friend. And this is my niche.

I’m Jennifer Raymond, founder of Jennections, and I’ve spent the past 20 years doing something more powerful than just cutting hair—I’ve been building trust, offering truth, and connecting people in ways that matter.

As a veteran hairstylist in Wellesley, Massachusetts, I’ve worked with CEOs, public figures, college students, and everyone in between. My chair has been a front-row seat to human nature—one that’s sharpened my emotional intelligence, deepened my understanding of people, and revealed just how much we all want the same thing: meaningful connection.

I didn’t seek out the matchmaking world—it found me. I became the person clients turned to for relationship advice, dating support, and tough love with heart. Now, I’ve turned that gift into a full-fledged service.

The Connector Behind It All

As an ENFP, social chameleon, and lifelong observer of people, I’ve always been drawn to deep conversations, personal development, and finding patterns where others don’t. My background spans psychology, design, tech, music, fashion, wellness and stoicism—and I bring that curiosity into everything I do.

At my core, I’m not just a stylist. I’m not just a matchmaker. I’m a Connector. And I help people connect—with others, and with themselves. I bring the beauty industry’s eye for presence, polish, and body language—and combine it with an intuitive, battle-tested understanding of human behavior and dating dynamics. I’ll help you refine how you show up in the world—from style to conversation to mindset—and attract with intention, not guesswork.

Whether you’re tired of dating apps, burned out by bad dates, or just ready to level up your approach, I’m here to help you avoid the usual pitfalls and elevate your presence in a way that feels aligned, effortless, and grounded in who you truly are.

Life Outtakes: