What we're about

The Thoughtful Gay Man Milwaukee is a discussion and support group for gay men and allies who want to live a life of more meaning, higher consciousness, and deeper connection outside of the typical "gay scene."

We gather once a month to explore a changing topic that takes us deeper into self-reflection, giving us the unique opportunity to give and take in a pool of wisdom with other gay men of diverse life experiences who understand us.

Wherever you are at in your life, whatever deeper questions you are looking to answer around the self, relationships, spirituality, the gay experience, etc., we welcome you as you are with the promise of respect.

We value empathy, openness, honesty, integrity, compassion, and building a real community. We are also wholeheartedly invested in our own personal, spiritual growth, as well as the growth of others. The purpose of this group is to encourage, uplift, and guide one another through this journey called life. Share your own life experiences, offer advice, and find support from other gay men. Join us if you're looking for deeper conversations, vulnerability, and other gay men who want to be their best selves.

During these Meetups you can expect: 
-conversations and ideas that will challenge you to grow as a person
-Leaving each gathering with more awareness of yourself and new perspectives on how to live the life you desire
-Time and space to explore, challenge, and discover your own assumptions and beliefs
-Meeting people that have similar and different experiences of life than you
-And an opportunity to make new friends! 
**There is no age, "race," or gender identity discrimination tolerated in this group - all are welcome!
**This is not a "singles" group.  But should you happen to find love...then, yay for you!

Welcome and we hope to see you soon!

Upcoming events (1)

Brotherhood Weekend Retreat for the Soul

375 Wood Rd


BROTHERHOOD means entering a space of vulnerability and authenticity without the fear of rejection. It means seeing the human in the circle of men around us, and truly being seen in return. It means connecting on the common ground of being gay men in need of healing, comfort, comradery, acceptance, and permission just to be from other men. It means letting down our guard and healing through self-exploration, deep discussions, meaningful connection, fun and laughter. It means cooking together, watching movies, being a kid again, and making lasting memories. It means relating to other gay men without the context of sex, drugs, or alcohol. It means forgiving the men that let us down, letting go of toxic definitions of masculinity, learning to communicate with other men, and allowing ourselves to trust other men. It means being welcomed exactly as you are, wherever you are at in your life, and no matter what you’ve been through. And that, in itself, can heal more deeply than we know.

If you hunger even slightly for any of the above, give yourself the gift of this December’s Brotherhood Weekend Retreat. There is no better time than the now. We are waiting for you.

Winter can be isolating, depressing, and lonely, so let’s be preemptive in giving ourselves a bright light to look forward to this season and help get us through.

On this retreat you can expect:

  • For the first half of each day, a schedule of guided exercises for self-exploration and healing, including guided meditation, journaling, art therapy, group discussion, and brotherhood-building activities
  • For the second half of each day, ample time to bond naturally as we share meals, play board games, watch movies, and relax by the warmth of the wood-burning fire
  • Daily vegetarian brunch and dinner provided (dietary restrictions can be accommodated) as well as light breakfast items (fruit, yogurt, granola bars, etc)
  • The gay “ summer camp” (only during the winter 😉) we didn’t get to experience as a child

Located at “The Haven” in Kenosha, Wisconsin – a geothermic designed home nestled into 24 acres of forest and meadow, encouraging a slower, quieter pace. Modern amenities are well placed through-out the house, including bathtubs and luxury showers. Bedrooms are spacious and minimal. The kitchen is fully stocked with cookware, coffee/tea station, and dishes for in-house meal making. The gathering space centers around a free-standing, wood-stove copper fireplace. Curl up with a book, or settle in for a movie marathon, or just enjoy a glass of wine with friends by the fire. Laundry facilities on the premises. 5-6 parking spaces provided. Access to parks, down-town shopping, restaurants and cafes - all within 5-10 mins drive. Take a look at the photos uploaded below.

No pets, no smoking, no drugs. Alcohol will be present and partaken in responsibly.

The Airbnb is reserved from Thursday evening, December 1st through Monday morning December 5th. It is understood that some may not be able to arrive until Friday evening due to their work schedule, and so arriving Thursday evening is an optional bonus that we hope you can partake in at no additional charge with dinner included. If you need to leave Sunday evening due to work on Monday morning, that is also understood, though it is ideal if all could attend Thursday through Monday to get the most out of the experience.

There are 4 bedrooms with 1 king bed, 2 queen beds, 1 bunk bed, and 3 air mattresses with all bedding provided. Cost will be less for those that request air mattress. Bathrooms will be shared.


  • $525 per person for 4 nights on regular bed, meals included (update: all beds taken, only 3 air mattresses are available with all bedding)
  • $475 per person for air mattress 4 nights meals included
  • Discount for couples sharing a bed ($785 total)
  • Payment must be sent as "friends and family" via Paypal
  • If cooking is your thing and you'd like to provide a meal throughout the weekend, you can subtract $35 from your total cost
  • If you would like to donate any amount for a scholarship for someone to attend who can't afford it, please message me and let me know.
  • If you would like to add a private coaching session with me during the weekend, you can add $75 (normally $120)
  • Given the limited parking space, carpooling if possible is ideal
  • This event will also be posted in the TGM Chicago group and so rsvp's may not reflect accurately as the event cannot be combined on Meetup's system.
  • For some reason the address comes up weird in apple maps. Wood Rd is also 30th ave. The driveway is directly across from 4th Street. It’s a long gravel driveway you go down. It’s north of Petrified springs park and north of Hwy A.

So looking forward to seeing you there! -Roy


Past events (158)

What We See in the Mirror

Milwaukee LGBT Community Center

Photos (231)