36M with bad dating experiences in the past, happy single then someone comes in and messes me a bit

For me to come to reddit talk about this stuff means I'm pretty insecure when it comes to dates and relationships.

TLDR: never had much luck dating in the old times, life became complicated in the last few years but I was feeling positive and happy single and fixing it, then girl shows up, gives multiple signs and then becomes silent for no reason as I was about to ask her out.

When I was younger I didn't have much confidence asking girls out. I would eventually, after developing enough trust and confidence, but for me that takes time. I don't fall for a girl quickly and when I do it means I really like her but I need time to slowly build my approach before I can ask her out or try something else. But I was also very oblivious to flirts and I am amazed at the girls who actually tried in the past and I totally missed when I thought nobody would want anything to do with me, only realizing a long time after that. A few cut me off completely out of the blue and I didn't even know why - to this day I'm not still sure if they were into me because the signs were so vague that I don't know for sure why they suddenly went from friendly to no contact. I have no patience for crowds, clubs or discos and I hate one night stands. I also dislike when girls play games with me. I thought these were teen things that wouldn't happen with slightly older woman, but I guess I was wrong. A few years ago I totally got out of my comfort zone and asked a girl out, eventually telling her more, which didn't work out so well because I came a little too strong but I didn't feel regrets and her further reactions made it clear she wasn't worth my time. At my current age I just wish people would accept things better and were more straightforward instead of playing games.

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I was slowly fixing my life on my own, even though I'm still professionally very unstable but there were some improvements that actually made me smile and happy about it. I have some close friends who support me as well and I wasn't expecting anything with anyone, let alone a relationship, especially after getting used to remaining single and feeling good with it. And then, when I least expected, this girl walks in...

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Met her during work, like several other girls. She's younger. Even though we work on the same place for now, we only meet for a pretty short period and she's usually very busy. I noticed she was cute, but that's it, nothing else on my mind. We started to talk normally, eventually she becomes nice to me, which is normal. But then she becomes nicer and starts greeting me better, calling me cute names, touching here and there, trying to build conversation and asking small questions in moments I don't feel talkative. All that when I still remained in my comfort zone without anything else on my mind. She also made some reference about liking my company and eventually made it clear she was not in a relationship (like... she told it straight). Not too long ago there was a group meeting I was going to skip because it involved people I barely know, but she asked me a few times to go and I eventually did. I was not sure how it would go, but well, it went pretty good. She was excited to see me there, sat very close, was hanging around all the time and even gave me her phone number at that moment. Some time later I was feeling quite depressed, she notices, catches me alone one day and tries to find what's wrong. I tell her, she surprises me with her support and availability to help. And that's when I started to feel something for her as well. I was still building my confidence, especially in my current situation. I started to text every once in a while and things were going good. Eventually a short vacation comes for me and on my last day before that I am very positive that she changed her routine on my last day so she could stay close as it felt like something she normally never does. As we wave goodbye for the moment she says we'll keep in tough. And here I thought: okay, maybe it's time to ask her out? So I sent her just a couple of messages to see how it goes, asking how she was doing before jumping to the invitation. The dialogue was short lived though, as she became silent for a few days, I know, this might mean nothing especially because she and I'll eventually talk to her again, but now I'm feeling quite insecure to contact her again like I haven't felt in quite a long time. All points out she might like me, but I can't find out unless I try and I'm afraid of coming too strong like the last time and I'm actually afraid of missing out this time, that's the main concern. And here I was living a happy life before all this. Sorry, just had to share.

Submitted April 12, 2019 at 09:23AM

For me to come to reddit talk about this stuff means I'm pretty insecure when it comes to dates and relationships.TLDR: never had much luck dating in the old times, life became complicated in the last few years but I was feeling positive and happy single and fixing it, then girl shows up, gives multiple signs and then becomes silent for no reason as I was about to ask her out.When I was younger I didn't have much confidence asking girls out. I would eventually, after developing enough trust and confidence, but for me that takes time. I don't fall for a girl quickly and when I do it means I really like her but I need time to slowly build my approach before I can ask her out or try something else. But I was also very oblivious to flirts and I am amazed at the girls who actually tried in the past and I totally missed when I thought nobody would want anything to do with me, only realizing a long time after that. A few cut me off completely out of the blue and I didn't even know why - to this day I'm not still sure if they were into me because the signs were so vague that I don't know for sure why they suddenly went from friendly to no contact. I have no patience for crowds, clubs or discos and I hate one night stands. I also dislike when girls play games with me. I thought these were teen things that wouldn't happen with slightly older woman, but I guess I was wrong. A few years ago I totally got out of my comfort zone and asked a girl out, eventually telling her more, which didn't work out so well because I came a little too strong but I didn't feel regrets and her further reactions made it clear she wasn't worth my time. At my current age I just wish people would accept things better and were more straightforward instead of playing games.​I was slowly fixing my life on my own, even though I'm still professionally very unstable but there were some improvements that actually made me smile and happy about it. I have some close friends who support me as well and I wasn't expecting anything with anyone, let alone a relationship, especially after getting used to remaining single and feeling good with it. And then, when I least expected, this girl walks in...​Met her during work, like several other girls. She's younger. Even though we work on the same place for now, we only meet for a pretty short period and she's usually very busy. I noticed she was cute, but that's it, nothing else on my mind. We started to talk normally, eventually she becomes nice to me, which is normal. But then she becomes nicer and starts greeting me better, calling me cute names, touching here and there, trying to build conversation and asking small questions in moments I don't feel talkative. All that when I still remained in my comfort zone without anything else on my mind. She also made some reference about liking my company and eventually made it clear she was not in a relationship (like... she told it straight). Not too long ago there was a group meeting I was going to skip because it involved people I barely know, but she asked me a few times to go and I eventually did. I was not sure how it would go, but well, it went pretty good. She was excited to see me there, sat very close, was hanging around all the time and even gave me her phone number at that moment. Some time later I was feeling quite depressed, she notices, catches me alone one day and tries to find what's wrong. I tell her, she surprises me with her support and availability to help. And that's when I started to feel something for her as well. I was still building my confidence, especially in my current situation. I started to text every once in a while and things were going good. Eventually a short vacation comes for me and on my last day before that I am very positive that she changed her routine on my last day so she could stay close as it felt like something she normally never does. As we wave goodbye for the moment she says we'll keep in tough. And here I thought: okay, maybe it's time to ask her out? So I sent her just a couple of messages to see how it goes, asking how she was doing before jumping to the invitation. The dialogue was short lived though, as she became silent for a few days, I know, this might mean nothing especially because she and I'll eventually talk to her again, but now I'm feeling quite insecure to contact her again like I haven't felt in quite a long time. All points out she might like me, but I can't find out unless I try and I'm afraid of coming too strong like the last time and I'm actually afraid of missing out this time, that's the main concern. And here I was living a happy life before all this. Sorry, just had to share.