Hi Dr. NerdLove,
I’ve stumbled across this site about a year ago and have really been reading and trying to take your advice in all kinds of areas of my life. I have always been fearful of showing my vulnerability to people and it even lead to issues with some of my ex-girlfriends. I have for the past few years been improving on and genuinely showing myself off to people. The reason I did this was because I tend to have a lot of people who end up letting their guard down with me very easily and telling me about their mental health struggles such as depression, suicidal thoughts or attempts, cutting themselves, abuse, etc and they find I’m a very easy and caring person to talk to about this. I didn’t want to feel like burdening people who may have those issues with problems going on in my own life that felt minuscule in comparison, so I hid it. It was unhealthy I admit, but I was doing it for what I thought was for the benefit of someone who was suffering in my eyes. These days although I am still someone who hears this kind of stuff, I have made it more of a mission to be more active in saying how I really feel when asked rather than always replying “I’m fine.”
My problem I still have yet to fully overcome, however, is really expressing attraction to people I actually would like to have sex with. Granted, women (and men) have told me that I am quite attractive and I have for years even had women chase after me to either become a boyfriend or do sexual activities with me, but I was always someone who was just passive with it all. I’ve had a total of 5 relationships so far and all of them were initiated by the women asking me out. I lost my virginity only a few months ago and it was due to me striking up a conversation with a women who sat by me in a bar and she slid over her number after the conversation to which I followed up on and had sex which she said I was an enjoyable partner. For reference, I am 23 now.
I keep thinking in the back of my mind that being too forward about maybe getting a Friends with Benefit situation or even a one-night stand to be inappropriate (despite the fact I know women are also sexual beings). Thus, I feel like I have to always be super respectful in that category, which leads to me being really slow to initiate things sexually, even though I am confident in expressing interest in general attraction more generally although again in a passive manner.
So I want to ask, what can I do to become more confident in being active in my flirting and being comfortable just trying to get sexual relationships without much else attached? I don’t just want to keep being the passive guy who although can occasionally get females interested. I largely just never go after who I want due to my own insecurities about the man I’m trying to be.