I’m [26M] very rusty at the regular dating game. How do I approach dating a woman [25M] after several years of not dating for a relationship.

For the past few years I sorta emotionally screwed myself. I maintained basically a very close emotional relationship with a poly friend, we never had sex but she was in my life 95% of the time where so much of my energy went and everyone thought she was my gf. During that time I dated, but it almost exclusively ended up being short term or just for sex.

I’ve only been seriously dating, looking to cultivate a relationship for three months and have gone on three dates, only one which is now leading to a second date. We chatted for almost a month before meeting up. The holiday travel sorta messed with our schedules.

To be honest she is just the the type of woman I know I’ll get on with. I’m trying not to go overboard with anything. I’m not the type of guy that likes to go directly to sex, I’m shy and sorta slow and usually wait for cues from the woman. But the opposite has sorta been the norm for so long.

What are the rules anyways? She broke the physical barrier by hugging me a couple times. Do I ask for a kiss this time? She’s also shy, particularly adorable, sorry side tracked. I don’t want to come on really strong.

She’s also traveling a ways to visit me. I travelled to meet her, now She wanted to travel to see me because I made the effort. Either she’s just too nice or it’s a good sign. We’ve bonded over cooking and being foodies. Would it be going overboard to make her some cookies we talked about.

I know I’m definitely overthinking things. I’m trying to be considerate and get to know someone as an end.

TL;DR: Really just starting to date for a relationship. Going on my first successful second date in a while. I’m so rusty at this. Should I ask her for a kiss? I’d really appreciate advice?



Submitted January 20, 2022 at 12:09AM

For the past few years I sorta emotionally screwed myself. I maintained basically a very close emotional relationship with a poly friend, we never had sex but she was in my life 95% of the time where so much of my energy went and everyone thought she was my gf. During that time I dated, but it almost exclusively ended up being short term or just for sex.I’ve only been seriously dating, looking to cultivate a relationship for three months and have gone on three dates, only one which is now leading to a second date. We chatted for almost a month before meeting up. The holiday travel sorta messed with our schedules.To be honest she is just the the type of woman I know I’ll get on with. I’m trying not to go overboard with anything. I’m not the type of guy that likes to go directly to sex, I’m shy and sorta slow and usually wait for cues from the woman. But the opposite has sorta been the norm for so long.What are the rules anyways? She broke the physical barrier by hugging me a couple times. Do I ask for a kiss this time? She’s also shy, particularly adorable, sorry side tracked. I don’t want to come on really strong.She’s also traveling a ways to visit me. I travelled to meet her, now She wanted to travel to see me because I made the effort. Either she’s just too nice or it’s a good sign. We’ve bonded over cooking and being foodies. Would it be going overboard to make her some cookies we talked about.I know I’m definitely overthinking things. I’m trying to be considerate and get to know someone as an end.TL;DR: Really just starting to date for a relationship. Going on my first successful second date in a while. I’m so rusty at this. Should I ask her for a kiss? I’d really appreciate advice?
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