Hi there, thank you for reading and for the advice. I by no means intended to convey that I am resentful toward my friendships or have taken them for granted (I don't think that's what you were implying either but your remarks on this have made me realize what I was really saying there). I am incredibly fortunate to have them and will be forever grateful for them being so accepting of me throughout the years. I was just thinking that in hindsight, having "fallen in" to my friend group may have caused me to be a bit less comfortable with putting myself out there in the long run. Your recounting of your experience has really put things into perspective for me, thank you for that. Your advice on starting conversation after the "mutual silence" is awesome, that's something I struggle with a lot. Getting in my own head about how I'm going to start the conversation and next thing you know it's been 10 minutes and it's going to be weird to start talking out of the blue. I think the part I'm really struggling with, however, is *after* that initial conversation. The whole, giving them my phone number and actually following up bit. That's where I fall on my face. It seems so simple but for whatever reason I just can't wrap my head around it. "What would we do?" "What if they're not interested in what I suggest?" "What if they were just being nice and aren't really all that interested?" all fly through my head and I end up chickening out. Anyway, thanks again, truly. This was an awesome response.