(30M) Thoughts on admitting that you can't react to hints

Hey folks,

Let me start by saying that English is not my first language, and that I know I can be strange, and I promise I’m trying to get better and to not harm anyone. 

I recently went on a couple of dates and it made me Really think about one of the problems I’ve been having throughout my life in dating/relationships, which is reacting to hints from girls.

I went out with a girl I met on a dating app. This was the second date. And we ended up walking home after dark, after having a picnic that turned into sharing a bottle of wine in the park.

She talked about enjoying a good run so I ended up jokingly racing her, and, after winning the race, "asking for a prize" . Which lead to me presenting my cheek to her and getting a glorious kiss on it. After that, she looks me in the eye and asks me if that's all I wanted for a prize. Hearts beating fast, tension rising, eyes locked. I break eye contact and say "Yup! " and move away joyfully like a clueless derp. Now comes the bad part.15 minutes later , when I walk her home, before saying our goodbyes I remember that interaction and say something like "you know what, I've been thinking, I really did want something more". Then I move to kiss her.  Please punch my teenage brain in my adult face.

It was not forceful. I promise.She backed away, I backed away, it was okay. I checked with her after and she was okay. But it was Enormously awkward. It’s now been 48 hours. I’m still physically cringing. Sigh. Please punch my teenage brain in my adult face.

Anyway. This made me think harder about this recurring thing that happens, in that I cannot react to hints, and sometimes I think I see a hint and I act on it and it ends up being awkward, or downright bad.

I have some, but little experience in dating. I had 2 1-year relationships and maybe 2-3 short reciprocated attempts at forming a relationship. Similar things have happened in the past, at different levels, from girls subtly asking me out, to them offering to have a drink while at their place, to ... more intimate stuff.  And I feel like whenever I would try to react to them, or wait for them to make a move, things would end up being awkward. When I wait for them to propose the next date, or initiate the next conversation, they either don't, or they do it like this girl did and I don’t get it, or get it too late. 

Now, one of the things I am unable to do, is blame myself for not Trying to be less clueless. Reading books/stuff on the internet, talking to friends and other people, therapy to some extent, I really have tried,  but, now in my early 30s, I kinda have a feeling I might just have to "work  around it", rather than correct it.

So here's what I've been thinking:  what if, instead of picking up clues, I settle in with being the initiator, and try to be happy with just what I get from my "initiations"? Like "would you like to hold hands", to " could I kiss your hand", all the way to intimacy. Give up on keep trying to read the signals, and just ask and initiate every time. Almost fully proactive.

What if I keep being a very timid, very reliable initiator, and enjoy my wins there? Earning my satisfaction from making good attempts and my validation from them accepting, rather than them initiating back.

What if, instead of thinking that she wanted us to share more than a kiss on the cheek, I take the kiss on the cheek and I’m happy and I think about it when I get home, and next time try to work off of that to escalate it to something a bit more.

Have any of you guys felt like this, or tried to “settle into the initiator role”, or have friends who have done it? What do you think?

Thanks for reading. I wish you all nice dates and long relationships with cool people.

TL;DR - guy in his 30s can’t catch a hint and wants to give up on catching hints and accept being the sole initiator in his relationship. How outrageous/unheard of is it? Comes with a side of awkward. Promises he’s not a serial killer/if a serial killer it’s on accident and willing to do better.