A
female
age
18-21,
anonymous
writes:I have a guy friend (fake name – Jackson) and we have been flirty friends but never dated or done more than a kiss on the cheek. We have dated other people but always kept our relationship in the friend zone. We both don’t believe in FWB and consider that wrong. We do talk about sex but just like in a generic way friends do. I tease him for being a man whore even though he says he has only done it twice. He calls me the ice queen as a joke because I am a virgin and have turned a lot of boys down.The deal is he was on his tablet in my room and we were done studying and I accused him of looking at porn as a joke. He denied it but would not show me what he was doing though so when he went to the bathroom I checked out his tablet. I know his password because he is so obvious and uses the same password for everything. I know that was wrong but I am already admitting that. It was no porn but just relationship chat rooms. I did not read the chats but I figured out his profile name. His profile was very poorly done btw with a not great pic and he could do so much better.So here is the bad part. When he was gone I started going to the same chat site and made up a phony profile to see if he would sign on and my plan was to get him to say something crude and rude and bust him on it like a prank because he is always Mr. Polite. He eventually signed on and I followed him into a chat room. I swear it was called “crush on my best friend” with all these people talking about having the hots for their friend. It did not take long for him to start talking and saying he was with his friend all day and he could not stop thinking about her and he said other things that made it obvious to me he was talking about me. I just lurked and watched him pour out his heart about how bad he wants us to be a couple how he has to hide it whenever he gets aroused around me and how he has all these fantasies of asking me out and being intimate. It was not gross porno talk but like super sincere. He also admitted he was a virgin and lied about having sex to impress me. I decided against the prank and just signed out when he did. So what do I do? I have this information about how he truly feels but I got it in a sneaky way. I also know his secret that he is still a virgin. I am not mad he lied. It is kind of sweet he wanted to impress me. He does that with other things trying to do sporty things even though he is not an athlete. Deep down I sometimes think of him as a potential BF and what a good BF he would make for someone, but I never considered us seriously as a couple. The things he said in the chat about how he feels about me totally melted my heart and now I see through so many things he has said and done to hide his feelings and act normal around me. Other people have said he was crushing on me but I did not believe it and he would always joke about it and say me asking meant I had a secret crush on him and we laughed it off. Now I feel like crap because he was trying to see how I felt and I shut him down. He really is a nice boy with good hygiene and a cute face. He sort of reminds me of that boy Robert Irwin whose dad was that Australia crocodile guy who died. He has a great smile. He is wicked ticklish which could be sexy. He has slightly defined abs although he admitted he was flexing them to make them stand out and his arms flex kind of sexy when he puts his hands behind his head. He would be fun to look at shirtless but he does not do that very often. Most of the guys who do weights are brainless in my opinion so if you ask me his normal boy body is way sexy enough. He is very smart at a lot of things and is great at listening and encouraging me. He can be funny and sarcastic but not in a mean way. He needs fashion help and sexier glasses (or maybe contacts) but that is easy to fix. I am open to giving us a chance as a couple, but how do I do it? Do I confess I spied on him? Do I call him out on being a virgin? Do I apologize for calling him a man whore? Do I just randomly encourage him so he makes a move finally? Any idea on how to drop hints or encourage him? Do I just ask him myself if he would like to try dating each other and pretend it was my idea? How can I give him more confidence so he knows he is a good catch just the way he is?
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female
reader, anonymous, writes (18 June 2022): I wouldn't admit to what I have done.
I wouldn't have done it in the first place but that ship has sailed.
Just stop playing games with him and be vulnerable. Tell him that you like like him. Share something personal.
He probably thinks that you are perfect and that you deserve someone better, more experienced, more everything. Let him know how much you like him.
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