My best friend and I are sort of dating right now, and I don't know how to make the transition from his "bro" to his "girlfriend." Help?

[tomskeezlez]

I've liked my best guy friend for two of the three years I've known him, so I was elated to hear a few weeks ago that he feels the same after all this time. We're in the 10th grade now, but he'd moved a little far during 8th grade, so I haven't actually seen him in person besides Skype for almost three years, but just recently, he's moved close to us, so all of this just sort of seemed like it was falling into place -- I've got the guy that gets me more than any other guy I've ever met and treats me extremely well, and we already know eachother, so things aren't supposed to be awkward, right...? Wrong.

When we were in middle school, I was a tomboy -- I still am, though SOME things have changed a little, like how I make more of an effort to dress nicely instead of my usual T-shirts and jeans (though I still throw those on sometimes) and I was always his "bro" -- I was one of the only GIRLS he could talk about his interests with (video games, sports, yada yada), and I wasn't really fake or superficial, so as time went on, he started to confide in me about alot more stuff, and I, him. We could talk about or make jokes about ANYTHING without many barriers, from innuendo-filled puns to racial jokes. But in more recent years, he'd been complimenting me more, and I guess that all led up to the night he told me he likes me. But since then, he's been slightly awkward about some stuff that he wasn't before. For instance, I'm black, and he's white, and I KNOW he's not racist, but he's been really hesitant about making black jokes. He knows I don't want to have sex before marriage, and he's known that for years, yet now it seems like he's afraid of making any jokes about it at all -- he said "That's what she said" once, and I laughed and thought nothing of it, but the rest of the conversation, his voice carried a little "Holy crap, did I just say something wrong?" nervousness. He's been set on assuring me that he's fine with my decision, and that he'd never force anything on me.

My point is, he's been working super hard not to mess things up with me, and I think that is just the sweetest thing a guy has ever done for me, but really, I know him -- we've been friends for years, and nothing he's ever said has offended me. We've never had an argument, he knows some things before I even say it, and quite frankly, I'm just as nervous as he is -- he's dated more people than me, and I've only had one boyfriend before him, and I'm not ANGRY at him for acting any different, because I understand he's trying NOT to be offensive. But I'm not acting any different from before. I just see our new relationship as a "status" -- in all honesty, it seems like we've been in a "flirtationship" at least a year before he actually told me he liked me.

NOTE: The reason why I say we're "sort of" dating, is because he's told me he "wants to make things official", so while he's asked me out, we haven't had our date yet, since we're going to get situated with school since It's just started, then we'll be going out (probably in a month or so).

[Always *]

Why do you need to change anything just cause you now know he likes you? I mean, all the explaining aside that IS what it seemed like you were trying to get at. He started liking you when you were a tom boy and all that other stuff, so now just cause he wants a relationship doesn't mean you need to bust out all GIRL on him and start wearing, like, butt loads of make up and 4 inch heels and, oh yeah, you need to STOP liking video games. I don't think you want to do that. I wouldn't sweat it. Plus your style will develop as you get older, just because you were a tom boy in middle school doesn't mean you still are a hard core tom boy, rather you just enjoy aspects of being a tom boy such as a more laid back style and enjoyment in video games and stuff. Who knows, by the time you are in university your style will probably be nothing like it was in grade 7. You can't assume that everything about who you are now will still be who you are in the future because people develop and change. Not completely, you'll still recognize yourself. But being a tom boy is ok. And he obviously LIKES that you are a bit of a tom boy. So really and truly, don't sweat it.

You guys will go on your first date and everything will work out

[FallingForGrace]

My bf and I were best friends too before we started dating. At first it was awkward too, but the thing about me, is that I'm honest to a fault. So one day I told him that I didn't feel like a couple, so we talked about it and then slowly we added in a "babe" then a "baby" then a few "Love yas" and eventually he was my boyfriend but still my pal. Like I still make fun of him like I would my other guy friends. He still makes jokes at my expense. The key thing here is to communicate. If you are ok with him being your bro while still being romantic, tell him so! Just say, "Hey, you know I'm still the same person right? I don't get offended easily, and I hope you don't either. I hope you know how I feel about you and that anything else that is said in good fun, is just that." Make boundaries. Like if he used to talk about girls he thought were hot and youre not comfortable with that, let him know in a light hearted way. For example "You can still make black jokes, but if I hear you say something about a hot girl, I'll go hood on you" and then laugh, so he knows youre joking. Like my bf and I, he still tells me if he finds a girl attractive and I tell him if I find a guy attractive (mainly when watching tv or something) because we trust each other. I know I'm the only one and he does too, and that comes from not only the loyalty we have as a couple to each other, but also the loyalty we have as friends.

[tomskeezlez]

Originally Posted by bumble bee

Why do you need to change anything just cause you now know he likes you? I mean, all the explaining aside that IS what it seemed like you were trying to get at. He started liking you when you were a tom boy and all that other stuff, so now just cause he wants a relationship doesn't mean you need to bust out all GIRL on him and start wearing, like, butt loads of make up and 4 inch heels and, oh yeah, you need to STOP liking video games. I don't think you want to do that. I wouldn't sweat it. Plus your style will develop as you get older, just because you were a tom boy in middle school doesn't mean you still are a hard core tom boy, rather you just enjoy aspects of being a tom boy such as a more laid back style and enjoyment in video games and stuff. Who knows, by the time you are in university your style will probably be nothing like it was in grade 7. You can't assume that everything about who you are now will still be who you are in the future because people develop and change. Not completely, you'll still recognize yourself. But being a tom boy is ok. And he obviously LIKES that you are a bit of a tom boy. So really and truly, don't sweat it.

You guys will go on your first date and everything will work out

Thanks so much for the advice! I think It's just jitters about the three years of waiting I did (I'd liked and had one or two sort-of relationships inbetween, but it was kind of shocking for my "best bro" to like me back.) But about what you said in the beginning of your post -- that I don't have to change anything about myself. Like I said near the end of my post, I haven't. I haven't been acting any differently, and I haven't started wearing tons of makeup (I look fine without it, and he says he's glad that I don't, because I look fine the way I am) so while I'm not going to say he's the only one that's nervous (I am. I truly am ), he's the only one that's acting differently. I DO have my own style -- I'm known for it -- and he knows that as well, in additional to the fact that it isn't going to change for him, or anyone else for that matter.

I'm also having a little bit of an issue with addressing him as my boyfriend and being flirty with him because, while I can easily flirt with other guys, and he knows I've become slightly more feminine than before, he has never seen me be flirtatious in person -- NONE of my friends have. They all seem to think, for some reason, that I'm either incapable of it, or that I'm (in their words, not mine) "too strong of a person to have a boyfriend". According to them, they figured that since I'm the confidant "I don't give a care what you think" kid that having a boyfriend "isn't my thing". Not that they thought I was gay, but that I just didn't seem the type.

[tomskeezlez]

Originally Posted by FallingForGrace

My bf and I were best friends too before we started dating. At first it was awkward too, but the thing about me, is that I'm honest to a fault. So one day I told him that I didn't feel like a couple, so we talked about it and then slowly we added in a "babe" then a "baby" then a few "Love yas" and eventually he was my boyfriend but still my pal. Like I still make fun of him like I would my other guy friends. He still makes jokes at my expense. The key thing here is to communicate. If you are ok with him being your bro while still being romantic, tell him so! Just say, "Hey, you know I'm still the same person right? I don't get offended easily, and I hope you don't either. I hope you know how I feel about you and that anything else that is said in good fun, is just that." Make boundaries. Like if he used to talk about girls he thought were hot and youre not comfortable with that, let him know in a light hearted way. For example "You can still make black jokes, but if I hear you say something about a hot girl, I'll go hood on you" and then laugh, so he knows youre joking. Like my bf and I, he still tells me if he finds a girl attractive and I tell him if I find a guy attractive (mainly when watching tv or something) because we trust each other. I know I'm the only one and he does too, and that comes from not only the loyalty we have as a couple to each other, but also the loyalty we have as friends.

Wow, it sounds like you and your bestie had a great relationship! (If you don't mind, could you tell me how it went?) Thank you so much for the advice -- I found your answer thorough and very helpful.

I think you're right about the communication -- while we DO talk about anything, and some boundaries are either already known, or have been set early. He's known for years that I don't plan on having sex before marriage, and when it came up in a conversation, he'd said exactly that: "I don't really care about sex... I mean, I DO -- I'm a guy, and I'd be lying if I said I had a problem with it. But I don't care about waiting, because that's what you want to do, and I respect that." But I guess I hadn't addressed his nervousness. Part of me did it because while he's a really reasonable guy who isn't afraid of admitting he's wrong (That's partially why the two of us have never had an argument -- we can both admit to our faults openly) but I've called him on being nervous before, and he adamantly denied it. I think he would talk about it shortly into our relationship, knowing him, but I think he feels he has to play the cool guy to A) Impress me, because he was burned pretty badly by his last girlfriend (she cheated on him -_-) and he's admitted to me a year back that one of his biggest fears was saying something to myself and our best friend (we're kind of a trio) that would make us never want to speak with him again, and B) because he feels that he has to take the wheel on things since he THINKS I have little to no experience with guys.


I was actually having one of our super-long phone conversations with him about a week ago, and we were both just clearing up misunderstandings we've had about eachother for the last three years, our thoughts on dating, boundaries, ect., and he'd asked me what type of girlfriend I was, since amongst pretty much all of my friends, no one knows of my "flirty side". To them, the idea of me flirting with a guy is kind of like this mythical beast -- I tell them about it, yet they're kind of on the fence in believing It's real because they've never seen me flirt with a guy in person. I only attend my new high school with one of my friends from my old middle school, but even my new friends know me as the confidant "I don't give a care what you think" kid, so I could care less whether they know about my romantic experiences because it would be pointless and not in my best interest to prove them otherwise. But my best friend knew I'd had one boyfriend before him (while I'd flirted and had "sort of" relationships with alot of people, only one had been an "official" boyfriend) he was wondering what the "flirty" me looked like, or if I even had a flirty side.

I explained that yes, I DO have a flirty side, and experience in doing so, and he just couldn't wrap his head around it. "Really? It's not that I think you're incapable of it... It's just that my image of you 'flirting' with anyone is kind of weird. In my head, the first image that comes to mind of you picking up a guy has a British accent for some reason, and a monocle and poofy dress, and when you approach someone, the first words that come out of your mouth are always 'Why, I find your face quite fetching, good sir -- care to dabble in a spot of tea in the noontime-hours?'" I had a good laugh at that, because I tend to use words like "fastidious" and "persnickety" on a norm, and it throws my friends, family, and english teachers for a loop, but it also kind of worried me... It means I have to set the bar. Again, flirting with other guys has been no problem for me, but with him... he makes me feel appreciated, which is all a person can want, but also small at the same time. Usually, the guys I flirt with are easily manipulated or won over -- give them a few compliments, and you've got a lunch date. But he makes me say really stupid things sometimes, so the confidant me is kind of gone out the window. Him simply complimenting me once or twice (calling me beautiful, sexy, ect) left me speecheless, since it was at a two-year mark in our friendship (He'd seen my dress that I wore to this dance, and was very flattering about it) and 'till then it had just been the two of us joking around... Quite frankly, I'm not sure how to respond to HIS flirty side either.