Should I (27M) go for her (30F)?

I have never been in a relationship and have not even been on a date. I am absolutely scared to ask out a girl on a date. I am scared of rejection and I am scared of what she might of me afterwards. I have lots of female friends and I don’t want them to hate me or think that I was only friends with them to get together with them.

I also am not particularly charming nor particularly attractive and I have always operated under the rule that if you like someone, chances are there someone else likes them too. I also don’t think I’d be a good romantic partner to begin with.

Normally this didn’t bother me, but as I grew older and saw my friends get into serious relationships and even marriages, I began to feel lonely.

As a high schooler, I always expected to come out of college as someone cool, mature, and confident and eventually get a stable career, a partner, and maybe a family. I did not expect to still be the same insecure and lonely person I was then.

Now as I am getting closer to thirty, the feeling of loneliness has been getting harsher and harsher. Especially as I have now been quarantining by myself. The loneliness is absolutely scaring me and I am now kicking myself about what I did wrong.

Anyways my coworkers and I used to drink after work at a bar and we are usually recognized by the bartender there. She is absolutely an amazing and beautiful person and someone who exudes confidence. She is essentially the embodiment of who I wish I Was. I am a social worker and am an essential personnel. Going back home by myself has had a surprisingly emotional impact on me. While we couldn’t go back to drinking after work like before, I decided to go back yesterday night . The bartender was there as always and she allowed me to stay after hours and talk with her. We’ve talked and chatted before, but it was always more of a bartender and a bar regular relationship. I must have gotten pretty tipsy since she called a driver over to drop me off. It turns out she wrote her number on my receipt.

Edit: while clearing out my jacket, i found out that out she also stuck a pad with her number into one of my pockets.

I don’t know what this means. Should I call her? Should I ask her out? Or perhaps I shouldn’t since she may have written her number since I forgot something while I was tipsy? Besides why would she want one with me and even if she wanted one with me, I doubt I’d be a good boyfriend so if anything I should do her a favor and not ask her out. And even if she said yes, she might be turned off when she finds out I never had a romantic or physical relationship or that never even kissed a girl.

What should my next step be? Sorry if it sounds like a rant, I am just anxious about what my next steps should be.

Submitted November 11, 2020 at 12:01AM

I have never been in a relationship and have not even been on a date. I am absolutely scared to ask out a girl on a date. I am scared of rejection and I am scared of what she might of me afterwards. I have lots of female friends and I don’t want them to hate me or think that I was only friends with them to get together with them.I also am not particularly charming nor particularly attractive and I have always operated under the rule that if you like someone, chances are there someone else likes them too. I also don’t think I’d be a good romantic partner to begin with.Normally this didn’t bother me, but as I grew older and saw my friends get into serious relationships and even marriages, I began to feel lonely.As a high schooler, I always expected to come out of college as someone cool, mature, and confident and eventually get a stable career, a partner, and maybe a family. I did not expect to still be the same insecure and lonely person I was then.Now as I am getting closer to thirty, the feeling of loneliness has been getting harsher and harsher. Especially as I have now been quarantining by myself. The loneliness is absolutely scaring me and I am now kicking myself about what I did wrong.Anyways my coworkers and I used to drink after work at a bar and we are usually recognized by the bartender there. She is absolutely an amazing and beautiful person and someone who exudes confidence. She is essentially the embodiment of who I wish I Was. I am a social worker and am an essential personnel. Going back home by myself has had a surprisingly emotional impact on me. While we couldn’t go back to drinking after work like before, I decided to go back yesterday night . The bartender was there as always and she allowed me to stay after hours and talk with her. We’ve talked and chatted before, but it was always more of a bartender and a bar regular relationship. I must have gotten pretty tipsy since she called a driver over to drop me off. It turns out she wrote her number on my receipt.Edit: while clearing out my jacket, i found out that out she also stuck a pad with her number into one of my pockets.I don’t know what this means. Should I call her? Should I ask her out? Or perhaps I shouldn’t since she may have written her number since I forgot something while I was tipsy? Besides why would she want one with me and even if she wanted one with me, I doubt I’d be a good boyfriend so if anything I should do her a favor and not ask her out. And even if she said yes, she might be turned off when she finds out I never had a romantic or physical relationship or that never even kissed a girl.What should my next step be? Sorry if it sounds like a rant, I am just anxious about what my next steps should be.