
 Conversations That Matter 10 Dating Tips for Guys
 Oct 7, 2025 
 Explore practical dating insights as Jon shares ten essential tips for men. He emphasizes knowing what you want and maintaining realistic expectations. Gradual approaches and meaningful conversations pave the way for connection. Jon advises avoiding desperation after rejection and stresses the importance of being direct yet respectful. Use technology wisely to facilitate real-life interactions. He highlights the need for undivided attention on dates and counsels against overwhelming a partner with future plans. Finally, he advocates for respectful relationship closure. 
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Approach Gradually
- Approach women gradually by observing and starting with low-pressure conversation.
 - Transition naturally to coffee or a casual meet-up when the rhythm of conversation allows.
 
How Jon Started With His Wife
- Jon recounts meeting women at church and starting brief, normal conversations to gauge interest.
 - He also shares he messaged his wife on Facebook and waited to give his number until after a coffee date.
 
Don't Overwhelm The Pond
- Don't immediately move from one rejection to asking her friends out because it signals desperation.
 - Give time and respect the social dynamics so your reputation isn't damaged among her circle.
 
