Dating Tips Articles

I’ve been a fan of the horizontal striped shirt for decades. It started when I was working on a photo shoot and pulled a Saint James traditional Breton striped one and fell in love. This was circa 2004. It was boxy and had a dropped shoulder and I wore that...

Maybe you’ve seen the summer 2025 trend of wearing tall boots (think riding boots, cowboy boots, or any variation that hits just below the knee) with shorts of varying lengths. Maybe you saw it on the ‘gram, maybe it was on a fashion blog, or maybe it was even on the...

Do you ever pull something out of your closet or drawer and suddenly put a date on when you bought it? I can always put a general time stamp on things based on: the year each of my kids were born, when I got divorced, when I met Yoav, and Covid. Well I finally (yes in...

There are many new people here so I wanted to take a moment to introduce myself and tell you how and why I am here as a (reliable) dating expert. And for those of you who have been here a while, maybe there’s something you didn’t know about me 😉 I started Style My...

Guys, I finally found some cut off jean shorts that don’t make me feel like I’m stealing my teenager daughter’s! They are not-too-short, no other rips or tears, and come in black which also makes them feel a bit more polished than a faded denim. AYR - The Sure Sure...

Entering or reentering dating in middle age is daunting for all kinds of reasons (as I very much know first hand). All the time I hear people saying "I'm too old for this." But — and I mean this from the bottom of my heart — dating in your 40s and beyond is so...

Online dating! At times so exciting… and at times so fraught. I’m a big proponent of taking dating breaks. That kind of advice is maybe not great for my business model 🙃 But when I see clients and friends reaching a certain level of frustrated, that’s really...

Nothing in the world makes me happier than hearing your success stories! (And to me, success of course means meeting the love of your life, but it also means going on amazing dates and feeling super confident all the while!) If you're wondering what it feels like to...

I recently made a crazy request to one of my clients. She's been going on a ton of first dates, which is awesome. But after each date, she'd tell me, "I just don't see a future with them." There would always be some x, y, or z reason why they weren't...

Raise your hand if you think you are a natural-born conversationalist! That's awesome if you feel that way... but it's also not true. No one is born knowing how to converse (literally). It's a skill you've developed and practiced and honed over time. Which means that...