Written by Sasha

Hi Sasha! So here's the deal: Last November I met up with a guy through lavalife for the sole purpose of hooking up. We met up for a drink and I had an instant attraction for him, not just because he's hot but his personality and sense of humour are killer. We made each other laugh the whole night. Sasha, I have never gotten along with a guy so well and had this kind of chemistry. So we went back to my place and had hot (safe) sex. Woo! But we both made it clear from the beginning that it wasn't serious; he had just gotten out of a long-term relationship and I have no idea what I'm looking for. So we're f-ck buddies. We've been hooking up every few weeks and it's great. The problem is that I'm developing serious feelings for this guy. Now I'm not the type of girl who falls for every guy I f-ck. I normally fling them away pretty easily but this dude is special. Sasha, I want to date him so badly it's killing me! So what do I do?? Should I just continue to have the best fling of my life and bury my feelings or should I spill? He hasn't let on at all that he wants to date, and although he has suggested going out to see a movie, we haven't done that yet. Sasha, what should I do? C

So you’re the f-ck em’ and chuck em’ type, huh? Well, this must be an interesting turn of events for you then. Listen, there’s ALWAYS one person that’s more ‘in like’ at the start - it’s just the way it goes and while you may have never been that person, it looks like it’s your lucky day. I think I’m safe in assuming that you’re the type that likes to keep your heart pretty protected so I get that you’d be fearful to dive in but if you’re asking my advice, I think it’s time to own these feelings of yours. F-ck if I know how buddy’s going to react but either way he’s gotta know where you stand, because there’s no way you can continue boning this dude while still keeping cool. It doesn’t matter how level headed of a chick you are, you’re not going to be able to bury those feelings for very much longer without turning into a crazy lady.

And I’m sorry to give you more bad news but you know that fling? Well, that fling as you know it, is over. Once real feelings come into the picture, that freestyle kind of f-cking is donezo – you’re in it for real.
Now something that I’ve noticed – which gets complicated if left too long - is when people right off the bat express they don’t want anything ‘serious’. I get why people do that, because lord knows if you want to tap out of it quickly it’s the best excuse, but sometimes that declaration can actually prevent things from going to the next level. So my hunch is that there’s a good possibility that he might feel the same way you do, but is too scared to say anything because you both agreed to not get serious. I mean, that’s the reason why you’re afraid to say something, right? No one wants to look like the emotional pussy in the situation but the only way to find out is for one person to grow some balls and say what they want – so C, I say you pony up and go get what you want.

Obviously don’t wig him out and confess your love but I definitely think you should start doing things with him in the real world. So yah, next time he suggests a movie, take him up on that and actually set a date. Actually even better - why don’t you ask him? Oh and make sure that when you do decide to go on that date, you haven’t swapped fluids with him that day. Okay? Good.

It’s been 4 months already so to me this sounds like a sh-t or get off the pot situation. Ya know? The sex, no matter how mind blowing, will get empty - quick. You’re at the stage where you want more, and if you’re not getting that from him I’ll bet money on it you’ll start to feel used. And sh-t, if he gets scared off by the idea of a movie or a dinner, then he’s a pansy ass loser.

Either way though I think you should start changing the dynamic of this relationship - it would be a shame to not see where this could lead. So stop denying what you feel and take a risk. Good luck and let me know how it goes!

Dear Sasha, I have a huge dilemma, my best friend and I have been friends since high school, and I’m 22 now. She hasn’t been the best person, she’s slept with a guy I kissed at a party ten mins after I left, she’s a nasty drunk and sleeps around, which would be fine but she’s always lying. I’m still her friend because I guess when it doesn't have to do with boys she’s great. Lately she’s started liking a guy named, let’s say Alex. Now Alex doesn’t like her back and everyone’s told her but she’s convinced there are "signs". A few weeks ago a group of us all go away to the beach for a couple of days and Alex and I got on really well, we opened up about past relationships (I, until 8 months ago had had a bf since I was 16 and like my ex, Alexs' ex cheated on him) and yes I know, but I’m developing feelings for him. One night we couldn't get to sleep so we were watching a movie on the couch and he sort of held my hand, now I don’t know if he was just being friendly or what- since I've been out of the game for so long, and some of my other friends have noticed he’s always trying to sit next to me and finds excuses to touch my hair or playfully shove me. If my best friend has noticed anything, she has not mentioned a word of it and I don’t know what to do. I know I can't go out with him or anything, but is he flirting with me?? Do I have to tell my best friend that he tried to hold my hand? Can I somehow keep my best friend and maybe him too? I know I should feel guilty about liking him, but she lies to him all the time telling him she was cheated on (when she cheated on her bf repeatedly a few times with his own brother, and I find it really offensive because my ex cheated on me and I know exactly how horrible it is ) and lies to him saying she’s not seeing/sleeping anyone (she’s sleeping with another guy regularly) and I just want to scream out "SHES LYING!!" . HELP ME! How do I handle this situation? Thanks T

Gawd, your friend sounds like a major liability. I’ll try not to bag on her too much but T, I hope you don’t trust this girl with too much because she really doesn’t sound all that stellar. Having said that, slutty crazy people can sometimes be pretty amusing to have around.

Anyway the answer to your question is pretty simple - do whatever the freak you want to do. Just because your friend pisses in circles around every guy it doesn’t mean you have to abide by her insecure ways. Remember Rayanne from My So Called Life? Oh god, you’re probably too young to know this show, but if you ever watch the series, which you totally should, you’ll get the Rayanne reference – your friend sounds totally like her. Ok, where was I? Oh right. In my opinion this doesn’t seem like a poaching situation at all. Obviously I believe in girl code, so yes, you should never go near someone your friend actually has real feelings for or has seriously dated in the past but this ‘Alex’ guy is free game.

First things first – when a guy tries to hold your hand, um, they aren’t doing it to be friendly. Even I know that. And all this shoving and hair playing is making me giddy, as it should you – so if you’re trying to figure out if he’s flirting, yes, he is. Now whether or not it means he wants to go steady, I don’t know, but I think you have the right to find out.

As far as what you should say to your friend. I think you should sit down with your homegirl and tell her that Alex tried to hold your hand the other day and you really liked it and you really like him. Also acknowledge the fact that you feel weird and uncomfortable about the situation (because she’s expressed her like for him in the past) but you really want to be honest with her so that she doesn’t feel like you’re doing anything shady. Now be prepared, she might get really upset but I think as long as you’re honest with your intentions then you’ve played the situation right.

Let me know how this pans out! I have a good feeling she’ll be marking her territory on some new guy before you know it.

I am 37 and decided to get serious about finding someone - went on the dating sites, stopped dating non-potential (but really hot) guys, etc. So I meet someone while out one night with a friend. Nice, cute, good job....and 7 years younger than me. Now I always counseled my friends about such things, but I figured, why not, go on a few dates. It's been a few months and we are both really into each other. Now, let’s put aside Demi everyone else, bc I live in the real world. Is the gap too big? It may not be noticeable now, but what about say, 7 years from now. Please don't say just have fun. I would like to have kids one day and just don't want to waste my time. Thoughts? Mrs. Robinsion ;-)

Okay I get why you don’t want to talk Demi and Ashton – they’re grating in-your-face relationship is one big yawn. So instead, can I talk about John Corbett and Bo Derrick? I just saw them on Oprah the other week and holy sh-t they are an adorable couple. The ease and adoration for each other was palpable and I think that’s what everyone should be on the search for. I mean they’re 6 years apart and can you tell? Yah, sort of, but it really doesn’t matter. But here’s the deal…the difference between an Ashton/Demi and John/Bo is the quality of their relationship. Ashton and Demi’s relationship is based on like fart jokes and who can twitpic faster whereas John and Bo, well, they actually have a real foundation. So Mrs. Robinson, if this guy has everything you’re looking for then don’t get in the way of it. If you find someone who gets you and loves you then I really don’t see why age is a big deal. Really, don’t make me have to get Aliyah on your ass.

Buddy is 30, he’s a big boy, so he can make his own decisions and if he’s down with you then what’s your ish? And I’m sorry, but this 7 year difference doesn’t even make me flinch. Once people get into their 30’s, 40’s and beyond they all look the same kind of oldness (yes, I know this isn’t a real word). My only bit of advice for you would be to not make mention of this age gap often -- if you make it an issue then I can guarantee you it will become one.

Now, the only instance where the age difference may get tricky is with this whole baby making situation. As you’re well aware you’ll need to get cracking on this pretty soon, so if I were you I’d wait about 4 more months before dropping the baby bomb – you’ll be able to gauge his mind frame pretty damn quickly. Of course there are a lot of guys his age who would bolt in the other direction but surprisingly I actually know quite a few who were into nesting at 30 - so fingers crossed he’s one of them.

So there you have it, I hope this helps! And I know you don’t want to hear it, but yes, HAVE FUN! Open yourself up and don’t place barriers where there doesn’t need to be any.

Attached – Bo Derek on Oprah.

Photos from Wenn.com