I’ll try to make this as short as possible.

I M24 have been going out for drinks every single day with a F22 for about 2 months now, by now 99% of men would have actually gone for at least a kiss, but I haven’t. I’m shy, introverted and sometimes lack self-esteem. She’s actually joked a couple of times that she thinks I might be gay due to so much inaction.

For context, I’m a virgin, never kissed anyone and never actually dated anyone. Always grew up thinking I was too young to do any of the above, and now I feel like I’m too old to do any of the above.
On the other hand, she has told me that in the past 12 months, she has slept with 6 different men. On top of that, she’s always judging them. Either because they didn’t make her orgasm, or because they had a small penis. Obviously making me even more insecure and anxious.

Why tonight might be the night? One of our friends in common has invited us to go clubbing tonight. I’ve never been to a club, but from what most people say, it’s an easy place to hook up with other people. We’ll get loose and I might actually get the courage to at least kiss her.

However, knowing her history, knowing that for all intents and purposes we’re simply good friends and knowing that she has always told me that she missed clubbing and leaving with someone at the end of the night, I feel like this will either be a great night out, or a shitty night where I’ll make no progress and might end up seeing her leave with another dude.

I’m just stuck on how to proceed and anxious of what she might think/feel. Do I just go for a kiss or do I wait for her to make any move first? If I go for the kiss, what’s next? Do I take her for a ride, we stop somewhere and get down of business? What’s the process like? How do I know if she’s enjoying or will I be one of the next guys that she always talks about?

I don’t know. I feel like I’m just rambling but it feels so strange that I feel the need for a step-by-step tutorial for something that’s so common.

ps: I’m also aware that there are plenty of red flags regarding her, but as much as I like her, I know and I don’t want anything serious with her.

ps2: She’s also told me that she dislikes condoms and in her entire life only used them once.

1 comment
  1. Your insecurities will make you a virgin til youre 90 if you let it.

    I used to be shy and quiet and I hated it so bad, I finally got so frustrated I forced myself to do things that terrified me. Obviously, since I’m female the rules are different since I could still be shy and quiet and get asked out on dates or have casual sex with men b/c they were the ones who did the chasing. That’s all I needed was men confident enough to chase me and I’d let them catch me.

    In your case you have to face your fears and either tell your friend the truth that you have been dying to kiss her. If she says why didn’t you… you could say that all the things she told you about her past – you thought she was signaling that she wasn’t interested.

    She may have told you all those things out of her own insecurities about why the F isn’t he making a move?? It’s possible you’re making her feel insecure from your inaction so she’s compensating by telling you about all the guys that do want her.

    I think you have to decide… either go for it and forget your insecurities about her judging you… or say NOPE and just close the door completely. Friendzone it is. Choose A or B… there’s no C option of staying in this limbo world forever. Step up and take the risk or get out of the way and let someone else have a turn.

Leave a Reply
You May Also Like