When do you know you're ready to date?

TL;DR - Guy isn't sure about dating but craves intimacy.

Hello everyone!

I (24/m) have had two major relationships in my life.

Before I tell my story, here's a little context about me: I am a decent-looking guy with loads of charisma. I used to perform stand-up comedy and play music at different venues. I am a bit shy in the flirting aspects of life but otherwise, pretty decent at socialising/meeting new people. I love my own space a lot and center my life around building a career, developing hobbies, etc.

Okay, so here goes:

When I was around 18, I met someone. This was my first love and first experience being with a woman romantically. Before that, I had short romances but nothing serious. We fell hard and fast in love, and soon became the world for each other. We lost our virginity to each other and considered our life together pretty awesome. This went great for a year, and then we realized we weren't the perfect match. However, we were quite incompatible in many ways. This was clearly a co-dependent relationship. We lived together and enjoyed all our moments but hardly shared how we felt deep down. We continued like this for three more years.

As college came to completion, I took up the courage and admitted that we should part ways. There were a lot of tears and heartbreak, but eventually, we knew it was the right decision. Or so I thought. Anyhow, being a guy fresh out of a long-term relationship, I felt like a free bird. So I flirted left and right, went crazy and struck every opportunity with women. Few months out of the relationship, I found someone amazing. She was the opposite of my ex in many ways, but much better in healthy aspects of the relationship. The biggest red flag here was that I wasn't over my first relationship and this eventually led to a lot of problems.

We were quite physical with one another and communicated about everything. However, after 8-9 months of being together, I realised the 'rebound' situation was only going to get worse and I need to take time to myself. We parted ways and I found myself in two heartbreaks.

It has been close to 6 months since then.

I haven't spoken to either of my exes and have no clue what they are up to. I only wish the best for them. Mentally, I am much better. I have been taking therapy all this while. I journal, meditate and mostly focus my life around building my career and pursuing further education.

However, deep down I never feel like I am over my first ex. Her memory often stays with me. Whenever I play the piano (or other instruments), I remember our connection that was often built on music. Once in every few days, I got into this spiral of thoughts that I messed up big time, and should not have left her. I know I am a much better person and my life has improved immensely without romantic relationship(s). I know all the good parts, still my heart doesn't feel open or free.

I have gone on dates and flirted with women, but eventually, I leave the 'chase' and just like spending time on my own. Nothing feels good enough. I know I have a sex drive and crave physical intimacy, but extremely scared of having a relationship.

Somewhere, I have made it clear to myself that I might genuinely not have a romantic relationship and that's okay. I don't mind going to my grave alone. Despite of being a good catch (as for what my lady friends tell me), I just don't know what to look for in a relationship.

Can someone relate to this? What has your approach to life been?

Submitted November 12, 2021 at 12:04AM

TL;DR - Guy isn't sure about dating but craves intimacy.Hello everyone!I (24/m) have had two major relationships in my life.Before I tell my story, here's a little context about me: I am a decent-looking guy with loads of charisma. I used to perform stand-up comedy and play music at different venues. I am a bit shy in the flirting aspects of life but otherwise, pretty decent at socialising/meeting new people. I love my own space a lot and center my life around building a career, developing hobbies, etc.Okay, so here goes:When I was around 18, I met someone. This was my first love and first experience being with a woman romantically. Before that, I had short romances but nothing serious. We fell hard and fast in love, and soon became the world for each other. We lost our virginity to each other and considered our life together pretty awesome. This went great for a year, and then we realized we weren't the perfect match. However, we were quite incompatible in many ways. This was clearly a co-dependent relationship. We lived together and enjoyed all our moments but hardly shared how we felt deep down. We continued like this for three more years.As college came to completion, I took up the courage and admitted that we should part ways. There were a lot of tears and heartbreak, but eventually, we knew it was the right decision. Or so I thought. Anyhow, being a guy fresh out of a long-term relationship, I felt like a free bird. So I flirted left and right, went crazy and struck every opportunity with women. Few months out of the relationship, I found someone amazing. She was the opposite of my ex in many ways, but much better in healthy aspects of the relationship. The biggest red flag here was that I wasn't over my first relationship and this eventually led to a lot of problems.We were quite physical with one another and communicated about everything. However, after 8-9 months of being together, I realised the 'rebound' situation was only going to get worse and I need to take time to myself. We parted ways and I found myself in two heartbreaks.It has been close to 6 months since then.I haven't spoken to either of my exes and have no clue what they are up to. I only wish the best for them. Mentally, I am much better. I have been taking therapy all this while. I journal, meditate and mostly focus my life around building my career and pursuing further education.However, deep down I never feel like I am over my first ex. Her memory often stays with me. Whenever I play the piano (or other instruments), I remember our connection that was often built on music. Once in every few days, I got into this spiral of thoughts that I messed up big time, and should not have left her. I know I am a much better person and my life has improved immensely without romantic relationship(s). I know all the good parts, still my heart doesn't feel open or free.I have gone on dates and flirted with women, but eventually, I leave the 'chase' and just like spending time on my own. Nothing feels good enough. I know I have a sex drive and crave physical intimacy, but extremely scared of having a relationship.Somewhere, I have made it clear to myself that I might genuinely not have a romantic relationship and that's okay. I don't mind going to my grave alone. Despite of being a good catch (as for what my lady friends tell me), I just don't know what to look for in a relationship.Can someone relate to this? What has your approach to life been?