Deep Dating Portland

Deep Dating is a three-session guided experience for thoughtful individuals seeking connections that go beyond the surface. Over three consecutive weeks, you’ll join a small, curated group for meaningful conversations rooted in life’s enduring questions—questions that help us make sense of ourselves and our place in the world.

• Three consecutive sessions

• Guided conversations centered on life’s big questions

• Short readings, films, or poems provided by email (under two hours of preparation), every conversation offers the chance to become wiser, whether or not it leads to romance.

• Private matching process after the final session

• The Death of Ivan Ilyich by Leo Tolstoy

• Films like Her and In the Bedroom

• Short stories like Miss Brill by Katherine Mansfield

The kinds of questions we explore together include:

• What makes a life meaningful?

• Are we who we've always been?

• How much is enough?

• Are we our work?

• Does thinking about death lead to a good life?

• Are the machines coming to get us?

At each session, you will meet, listen, reflect, and make sense together with others who are showing up with openness and a desire to learn and connect.

We often think chemistry is a spark we can sense in the first five minutes of meeting someone. We believe something deeper is possible. Connection, chemistry, and trust can grow as we spend time together, explore big questions, and let conversation reveal who we are. Over three sessions, you will have the space to build something real—something that cannot be rushed.

No profiles. No small talk. No pressure to perform.Just meaningful conversation, thoughtful exploration, and the possibility of real connection through a life of the mind.

After the final session, you will have the option to privately share if there is someone you would like to continue the conversation with. If there’s mutual interest, Premise will help make the introduction.