After reading some excellent advice from a fellow Redditor, I decided to give this another shot—this time with more effort!

About Me:

6ft tall, brown eyes, fit (I work out daily but not overly bulky).

Good-looking with a sharp sense of style—overall, I’d say I’m pretty handsome.

DDF, STI-free, and maintain excellent hygiene.

Based in Toronto.

Single and discreet due to the nature of my job.

Respectful, laid-back, and open-minded, always prioritizing your comfort and boundaries.

What I’m Looking For: I’ve always been drawn to women older than me (30 ). While “MILF” might describe my interest, I’m not specifically looking for someone with kids. My fantasy revolves around the dynamic of a younger, fresh-to-life guy (me) connecting with someone mature, experienced, and confident (you).

I’d love to start with a one-time encounter (ONS), but if the chemistry is right, I’d be open to something ongoing (FWB). I do have a preference for Asian women but am open to any race, as long as there’s mutual attraction.

Personality-wise, I enjoy the idea of initially being in a more submissive role during the flirting stage, letting you take charge. But when it comes to the bedroom, I’m ready to switch things up and take on a dominant role. I’ve been with older women before, and I’ve been told they’ve been impressed with my skills and the energy I bring.

The Plan: I’d love to chat first and ensure we’re on the same page. From there, we could meet in a public space, like a café, to get to know each other. I enjoy the thrill of flirting and the anticipation of what might happen, but I also want this to feel genuine, not transactional.

Ideally, you’d be near downtown or willing to drive. Just to clarify, I’m completely self-sufficient—I’m not looking for someone to take care of me.

Boundaries & Preferences: I’ve kept things relatively vanilla so far but am open to exploring new experiences as long as we’re both comfortable.

Safety First: Since I’m new to this, safety is a priority. I’ll need some form of verification (like a picture and a few questions) to ensure you’re real, and our first meeting will need to be in a public space—this is non-negotiable. I’m also open to a quick call to verify.

Final Thoughts: I’m excited to connect with someone who shares my interest in age-gap dynamics. Here’s to good chats, good drinks, great chemistry, and hopefully, a memorable night.

Thanks for reading! And shoutout to the Redditor who shared advice for us men pursuing our fantasies—you’re the real MVP.