Men, I need your help and advice! - How to date your best friend

[Rudolph26]

Okay, so next Friday my best friend is visiting and we plan to go on a date. I've mentioned him in my previous posts and we have been friends for 16 years now. So, I've never really flirted with him before but we both are attracted to each other and have always loved each other. So, the dating aspect is completely new for the both of us. I've never dated a close friend before, so I feel really uncomfortable with the concept. I don't want to make him feel awkward, especially since he is the one choosing if we should continue dating. I really like him and I really want this to work but I want him to be sure this is what he really wants.

So men, this is where you come in.

If your best friend and you decided to date, what would help reassure you of their affections without making you feel pressured or awkward? What would help you gain the clarity you need to figure out if this relationship could work and is something you want? I don't want him to guess with this, and I don't want him to feel he needs to rush to a decision for my sake either. I want him to really have the clarity he needs about this. What can I do to help him achieve that? Would touching him make him uncomfortable? Should he make the first move or should I? Should I dress up to help him see me in a new light? or should I just dress like I normally do? Would flirting make him uncomfortable?

Usually when I date guys I'm charming, a good listener, ask questions to get to know them or talk about something interesting, flirtatious, dress nicely and typically kiss them by the first or third date (depending on the guy). However, he already knows me. The only side of me he doesn't know is my romantic side because I never acted on my attraction to him. So, what should I do? I feel like I can't really treat this like a normal date because he already knows me. But, I also want him to know my romantic side, but I don't want to pressure him with it either. Any advice would be greatly appreciated!

[Canonp]

Hey, I always feel that anyone who wants to date should always date his/her best friend, (my thought though). So frankly it's awesome that you are to date your best friend. Let's put it in this perspective, your best friend knows your best character and your flaws clearly well. Meaning that he still wants to go out with you regardless of your flaws that he already knows, so, you won't have to pretend to be all nice because since he is your best friend, he already knows that. So kindly don't worry about how things will go because I feel that if he is your best friend, then things will turn out to be just alright.

Then concerning your romantic part that he doesn't know yet, I feel that you should just express it. I think that by doing this he will get to know that part of you better. And may be he will be amazed.. but above all just remain you. If you are nervous, it's just alright because if I were in your shoes I'd be nervous not to mess anything. As in, it's understandable..

You also stated that when you date guys you are always charming, kindly, just be extra charming and dress nicely too, (not normal dressing). Yeah.. he knows you well, but this is a date, a new phase, so I feel it's nicer to be more charming and interesting.

Conserning the question that flood into your mind like (touching him..Etcs), .. just let the vibe flow. Then I also feel like try to minimize flirting unless he starts it, (just my thought though).. because he is your best friend, flirting extremely may get wierd. (My thought though) as in concerning that, just take it slow, for the first date that is. Anyways, all the best

These are just my thoughts though. I hope it does help..

[Rudolph26 in reply to Canonp]

Thank you for the advice. I like that we are close friends, I guess I just want to break the ice on our friendship and show him that it's okay to view me in a more romantic way? He is a very respectful man and has always made me feel like I could be myself and enjoyed it. I'm actually shocked that he was interested in me as well when I told him as much. I guess I have a hard time finding a balance between the friendship and romantic aspect? I also don't want to cloud his judgment either, but I also don't want him to miss out on the romantic aspect either.