I don’t know if I should ask this woman out.

[Volcanferno]

We are both 28.  She seemed to JUST want to be friends, but she lived over 1,000 miles from me so it couldn’t have worked anyway.  We met in high school and I moved thousands of miles away.

 

Here’s the huge caveat.  She wants an experienced man and I have only ever had 2 girlfriends in my life, my last gf cheated on me because I couldn’t please her in bed.  Seeing that she said she wants an experienced man, I’m not sure how it’ll go over.

BUT… we have known each other for ten years.  She has already proven to be the best friend I’ve ever had, by far.  And she even surpassed my male friends in less than a year after re-establishing contact.  She’s the only person who I can expect a swift response from when it comes to texting.  
 

I literally think the world of her now after being the last person who was still kind to me.  I want to repay her somehow.  Should I ask her out?

[Volcanferno]

And… I accidentally posted in the wrong topic.  I don’t know how to change that, or delete this post so I can post it correctly.

[Gebidozo]

7 minutes ago, Volcanferno said:

Should I ask her out?

Of course not.

She isn’t interested in you romantically. She lives far away from you. She has very specific demands for a romantic partner that you don’t meet and that she has shared with you for a reason.

Most importantly: I thought you said she was your friend? I could never understand why some men would want to be romantically together with their friends. I’m a guy and I have a few female friends, the mere thought of sleeping with them would repulse me. It’s like having sex with a sister.

I can’t speak for women, but I’m sure very few of them would find it endearing or flattering that a person who they thought were their friend is actually thinking of getting into their pants. I absolutely can’t see how asking her out would be “repaying” her (?), unless by “repaying” you mean “creeping her out”.

Another thing: your last GF was clearly terrible, since she cheated on you instead of working out the problem or breaking up with you. You shouldn’t think less of yourself because of that; the cheating is her fault, not yours. That said, if you think you’re too inexperienced and not knowledgeable enough about how to please a woman, that’s just another reason to go out there, meet women, date them, and learn more about their sexuality, instead of thinking of hitting on your friend.

Women are very different, they like different things in bed, and there is no one universal way to please them all, so don’t let the atrocious behavior of your ex get into your head. Being good in bed is much more of an acquired skill than an innate one. Unless you have serious purely physical issues (in which case you should see a doctor and try to cure them), you can learn it.

 

 

 

[ExpatInItaly]

1 hour ago, Volcanferno said:

she lived over 1,000 miles from me so it couldn’t have worked anyway.

Does she still live this far away from you?