I (30M) feel lost; I am recently single after nearly a decade of two back-to-back LTRs. I want to start casually dating again but I don’t know where to begin and I am having some serious issues with my self confidence/image

So looking back at all that I’ve written, this post has turned out much longer than I intended, so sorry about that. TL;DR at the end.

Anyway, I am recently single. I spent most of my 20s in two back-to-back long term relationships (I was single for a mere 4 months between them). First I got my heart broken and then 5 years later I broke someone else’s. Not intentionally of course but as much as I loved her, we had issues. Issues that were easy to overlook in the moment but were becoming more & more paramount as our relationship became more and more serious. I am at turning point in my career (I am graduating medical school early next year) where those issues had the potential to derail me. On top of that, my relationship was alienating me from my friends and family. I also hadn’t been single in nearly a decade and so I was beginning to feel as though I was lacking a true sense of self. I didn’t have things that I liked to do, I only had things that we liked to do. Over the 5 years that we were together, I lost most of my friends and now I can’t remember the last time I did anything social with anyone besides my ex or her family. I know I made the right decision in leaving but I didn’t realize how lonely I would be. I was so miserable being alone that I got myself a puppy so I would have some companionship (great decision, I absolutely love him).

I’m here in this sub because I hardly have any idea how to date at all, let alone how to date at this age. I know 30 isn’t old, but I feel like I’m getting old. The only time I REALLY ever dated was when I began dating my most recent ex 5 years ago. My first LTR began as FWB so there wasn’t much dating there, and before that the extent of my dating experience was in silly high school relationships (I didn’t go on a single date while I was in college because I was hung up on a girl that was never available).

I’m not looking for a LTR right now because I want to develop and get to know myself more & medicine has me moving around a lot, plus it’s very time consuming. I would like to casually date though. I’d like to learn how to date and flirt with women and of course have the occasional romp in the sheets. I also really want to have kids sometime this decade, so I can’t stay single forever.

Honestly though, I just have no idea where to begin. I have profiles on several of the major dating apps but it’s become clear to me that I’ve lost any and all ability to flirt. I don’t get many matches to begin with but when I do, I can’t seem to keep a conversation going or even get one started sometimes. I can be funny at times but it tends to be by accidental happenstances. I’m not witty on the fly. I can talk to my patients about their diseases and what’s slowly killing them and I know how to save someone’s life when their heart stops. But it seems as though I have no idea how to be social with women. I’m not at all awkward, I just don’t know how to flirt, so I don’t.

On a final note, I am confident in the person that I am and the potential that I have. Objectively speaking, I’m Ivy League educated, I’m effectively a doctor (seriously I’m 9 weeks & one licensing exam away from signing my name with Dr. and MD on either end), I’ve traveled to more countries than most people can name, I’m decently wealthy with a massive earning potential, I drive a Porsche, and I have a Ducati and a Harley. Material things I know shouldn’t matter but I must admit to my own vanity, they make me feel a little better about myself. Subjectively speaking, I’m a kind, caring, compassionate and considerate person who just wants to do well by others and share the massive amounts of love that I have in my heart with somebody who wants to do the same with me. Yet despite all of that, I severely lack confidence in other ways. I used to be thin and handsome but over the course of medical school, I’ve put on a lot of weight and over the course of the last year-ish, I’ve developed motor nerve damage in my legs. I can still walk but I can’t do a lot of the things I used to love and things that I would love to do with another person like skiing or hiking and I am very self-conscious about how I walk (I need PT but just have not had the time). All-in-all, I feel the least attractive that I ever have and that makes me think who would ever want to be with me especially when there’s now so much that I couldn’t do with them? And despite the fact that I absolutely know how to please a woman (I LOVE going down on women and I am very, very good at it), I worry, probably unnecessarily, that my sexual performance overall will be nothing more than a disappointment to a new partner and it causes me a lot of anxiety when it comes to dating.

So there it is. I feel lost and hopeless in my love life. Sorry for the long-ass post. This is mostly just a rant, but any advice would be more than appreciated.

tl;dr: Despite knowing that I have many desirable qualities, I feel lost and hopeless because I’ve been out of the game for so long, I have a career that isn’t conducive to dating or relationships, and I feel terribly unattractive.

Submitted November 18, 2020 at 12:08AM

So looking back at all that I’ve written, this post has turned out much longer than I intended, so sorry about that. TL;DR at the end.Anyway, I am recently single. I spent most of my 20s in two back-to-back long term relationships (I was single for a mere 4 months between them). First I got my heart broken and then 5 years later I broke someone else’s. Not intentionally of course but as much as I loved her, we had issues. Issues that were easy to overlook in the moment but were becoming more & more paramount as our relationship became more and more serious. I am at turning point in my career (I am graduating medical school early next year) where those issues had the potential to derail me. On top of that, my relationship was alienating me from my friends and family. I also hadn’t been single in nearly a decade and so I was beginning to feel as though I was lacking a true sense of self. I didn’t have things that I liked to do, I only had things that we liked to do. Over the 5 years that we were together, I lost most of my friends and now I can’t remember the last time I did anything social with anyone besides my ex or her family. I know I made the right decision in leaving but I didn’t realize how lonely I would be. I was so miserable being alone that I got myself a puppy so I would have some companionship (great decision, I absolutely love him).I’m here in this sub because I hardly have any idea how to date at all, let alone how to date at this age. I know 30 isn’t old, but I feel like I’m getting old. The only time I REALLY ever dated was when I began dating my most recent ex 5 years ago. My first LTR began as FWB so there wasn’t much dating there, and before that the extent of my dating experience was in silly high school relationships (I didn’t go on a single date while I was in college because I was hung up on a girl that was never available).I’m not looking for a LTR right now because I want to develop and get to know myself more & medicine has me moving around a lot, plus it’s very time consuming. I would like to casually date though. I’d like to learn how to date and flirt with women and of course have the occasional romp in the sheets. I also really want to have kids sometime this decade, so I can’t stay single forever.Honestly though, I just have no idea where to begin. I have profiles on several of the major dating apps but it’s become clear to me that I’ve lost any and all ability to flirt. I don’t get many matches to begin with but when I do, I can’t seem to keep a conversation going or even get one started sometimes. I can be funny at times but it tends to be by accidental happenstances. I’m not witty on the fly. I can talk to my patients about their diseases and what’s slowly killing them and I know how to save someone’s life when their heart stops. But it seems as though I have no idea how to be social with women. I’m not at all awkward, I just don’t know how to flirt, so I don’t.On a final note, I am confident in the person that I am and the potential that I have. Objectively speaking, I’m Ivy League educated, I’m effectively a doctor (seriously I’m 9 weeks & one licensing exam away from signing my name with Dr. and MD on either end), I’ve traveled to more countries than most people can name, I’m decently wealthy with a massive earning potential, I drive a Porsche, and I have a Ducati and a Harley. Material things I know shouldn’t matter but I must admit to my own vanity, they make me feel a little better about myself. Subjectively speaking, I’m a kind, caring, compassionate and considerate person who just wants to do well by others and share the massive amounts of love that I have in my heart with somebody who wants to do the same with me. Yet despite all of that, I severely lack confidence in other ways. I used to be thin and handsome but over the course of medical school, I’ve put on a lot of weight and over the course of the last year-ish, I’ve developed motor nerve damage in my legs. I can still walk but I can’t do a lot of the things I used to love and things that I would love to do with another person like skiing or hiking and I am very self-conscious about how I walk (I need PT but just have not had the time). All-in-all, I feel the least attractive that I ever have and that makes me think who would ever want to be with me especially when there’s now so much that I couldn’t do with them? And despite the fact that I absolutely know how to please a woman (I LOVE going down on women and I am very, very good at it), I worry, probably unnecessarily, that my sexual performance overall will be nothing more than a disappointment to a new partner and it causes me a lot of anxiety when it comes to dating.So there it is. I feel lost and hopeless in my love life. Sorry for the long-ass post. This is mostly just a rant, but any advice would be more than appreciated.tl;dr: Despite knowing that I have many desirable qualities, I feel lost and hopeless because I’ve been out of the game for so long, I have a career that isn’t conducive to dating or relationships, and I feel terribly unattractive.