Talk to a team member
Schedule a call with a Leland team member who can help you explore your options.
Schedule a call
Description
This personalized 12-week program is designed for people who want sustained support in developing their dating confidence, communication, self-presentation, and decision-making. Rather than following a rigid formula, the program is adapted to your experience, goals, and real-life dating situations. • Phase 1 — Understanding Your Starting Point We begin by looking at your current dating life, previous experiences, strengths, recurring difficulties, and relationship goals. Together, we identify the areas that deserve the most attention. • Phase 2 — Confidence and Self-Presentation We work on how you see and present yourself, both online and in person. This may include your dating profile, photos, personal style, communication, boundaries, and the way you express interest. • Phase 3 — Conversations and Dating Skills We focus on messaging, starting and maintaining conversations, preparing for dates, managing nervousness, reading situations, expressing yourself clearly, and responding to rejection or uncertainty. • Phase 4 — Real-Life Practice and Feedback As you apply what we discuss, we review your experiences together. Post-date debriefs help us understand what worked, what felt uncomfortable, and what could be approached differently next time. • Phase 5 — Long-Term Progress Toward the end of the program, we consolidate what you have learned and build a plan that you can continue using independently. The program combines private live coaching with ongoing support through Leland messaging. You can share questions, profiles, messages, and specific situations between sessions for focused feedback.
What you'll get from this package
A clear understanding of your dating goals, strengths, challenges, and priorities
A personalized confidence and self-presentation strategy adapted to your personality
Detailed feedback on your dating profile, messaging, conversations, and preparation for dates
Ongoing post-date analysis and adjustments based on your real experiences
A long-term plan for continuing to date with greater clarity, confidence, and independence
Additional details
Coaching delivered via live sessions.
This program combines regular live coaching sessions with focused support through Leland messaging over 12 weeks. We work with your real experiences rather than following a fixed script. Each session responds to what is currently happening in your dating life while keeping your broader goals in view. Between sessions, you can share questions and relevant situations for feedback, then apply what we discuss before our next meeting.
This program is intended to be completed over approximately 12 weeks and includes an estimated 18–22 hours of coaching. Scheduling will depend on mutual availability. Any profiles, messages, or other materials you would like me to review should be shared through Leland before the relevant session. Between-session questions are welcome through Leland messaging, and I will normally respond within two business days. This coaching is educational and developmental and is not a substitute for therapy, medical care, or crisis support. The program does not guarantee dates, relationships, or a specific personal outcome.
Services included:
Dating Profile Review & Optimization
Messaging Strategy
Confidence Building
Date Planning & Preparation
Conversation Skills
Post-Date Debrief & Analysis
Talk to a team member
Schedule a call with a Leland team member who can help you explore your options.
Schedule a call
More packages from Stephen
Custom hourly · $69/hr
Get help with General Exploration, Dating Profile Review & Optimization, and .
Stephen also coaches for Film & Television and Acting. View all.

Offered by Stephen M.
Joined July 2026
Dating Confidence & Online Dating Strategy for Men
I have been advising men around dating, confidence and communication for many years, first naturally through friends and people around me, and later through private coaching and word of mouth. My work focuses on helping men improve their confidence, self-presentation, dating app profiles, photos, bios, messages, conversation flow, flirting, first dates and communication with women. The goal is not to teach tricks or fake confidence, but to help clients understand how they come across, what may be blocking them, and how to become clearer, more natural and more effective in real situations. As an actor with international life experience across Europe, the US and Asia, I also bring a strong understanding of image, presence, communication, body language and the way people are perceived depending on their background because ... everybody is different. My coaching is honest, practical and supportive. The goal is to make real progress, but without shame or judgment. I know dating and confidence can be sensitive subjects, and if you are here, it is probably for a reason. So we approach them with clarity, respect, kindness, and some laughs too :)
$1,100
18h–22h of coaching