Ask Dr. Tony Vol. 22

Fellas, Holidays got you down cause your dick is so dry? Ladies, Bummed that you can’t find a special santa to spend these chilly nights with? Does this sound like some shit you’d read on the inside of a terrible christmas card? Probably.
Fuck all that noise. I’m here to help you. This is that thing where you send me questions of the heart in search of my sage, untested and highly questionable wisdom. But, as always, I’m here to help so I’ll do my best. if you have any love related things that need fixin’, drop me a question at or leave your question in the comments below. I’ll do my best. I swear.

there’s this girl I dated for 3 weeks or so like 5 years ago. then she said she wasn’t up to a relationship or whatever and that was it. a month later I found out she actually had a boyfriend since 2 years! hahaha I didn’t expect it but I didn’t care cause I actually didn’t like her that much.

anyways, we have seen each other but always for like 5 minutes or so, small talk basically, but I don’t why since 2-3 months she keeps writing me on facebook that she ‘d like to hang out. the funny thing is that she actually has a boyfriend (and now is no secret)

I don’t get it man, I mean, we are not friends, why should we hang out after 5 years. I have a girlfriend and I’m not interested in her or anything and I don’t know if I should be just nice and chill with her and try to be friends or just ignore her.

It’s not a big deal, but I’m just curious to know what is she up to, what do u think? is it some carma shit? I think so, some people are crazy

I hate to be THAT GUY, but as a person who is terrible at both spelling and grammar, this may be the worst written question I’ve ever received. Impressive, my good man. I’m not even mad.

Anyway, if you have no interest in this girl and you’re in a relationship there is 100% no point in chumming it up with this girl. I have no clue what her angle is but, really, what could it possibly be that you’d be interested in? A new friend? get the fuck outta here. It’s either that or she’s trying to creep. In both cases, you seem not interested so you might as well just stop responding. There’s a good chance she’s in the midst of a boring long term relationship and just looking for attention. Attention that could lead to other things. So, yeah, ignore her. It’s for the best for all people involved.

Hi Love Dr. Tony,
i need your help once again. i’ve been dating a really great guy for a little over two months. he’s smart, funny, handsome, and a super good cook. the only problem is that i’m usually sexually frustrated. in the words of Kim from Outkast’s Kim & Cookie: he got his, i ain’t got mine.

i’ve tried to talk to him about it but nothing has really changed. am i being selfish? cuz this is kind of a big deal, imo. do you think there is a way for things to get better or should i let this one go over just this issue?

I’d like to think most men take a little pride in not being selfish assholes in bed. I’d like to think that, but from what girls tell me all the time about their boyfriends, I’m thinking I’m wrong.
Now, this could be a few different things. If he’s a premature ejaculator than that’s gonna be an issue that takes some work. If he’s simply terrible at sex, that’s something you can maybe help guide him through to improve his technique (perhaps tell that asshole to eat the pussy too…). If he’s fine at sex but completely oblivious to your needs (Those two things tend to not go hand in hand but for the sake of the discussion I threw it in there) then all you need to do is say “Hey, keep going…do that thing for longer…”. Communicate.
Unfortunately , I have a feeling it’s one of the first two options. Bummer. For your sake, I hope it’s the second. The thing about most dudes is that , ideally, we want to please the woman we’re with. It’s a point of pride for any man who respects his penis. So, if he needs a little heads up on how to do it the way you like it…just tell him. Most guys will want to improve themselves. But , seriously, any dude worth his salt will get a girls first orgasm outta the way before he even starts having sex with them. Do the kids not do foreplay anymore??!?!

Alright Dr. Tony, lets see what you got.

Where to start with this shit? So I’m in my third year of college, still a virgin, good enough looking dude, like I get looks from girls/ approached at the bar, whatever. Just saying i’m no fucking ogre with acne all over his face creepin on girls with Shakespeare lines. So anyways, I’ve known this girl for the past two or so years now, and we’ve been really good friends, have a lot of the same friends etc, and she originally liked me back when we first met but I never found out till later when she had a bf. Anyways, her and her bf end up breaking up and we end up hooking up, just once, this one night. Like nothing crazy, just some foreplay but it was sorta weird between us since we’d been just friends for so long at this point. So maybe two weeks or something after, she ends up hooking up with this other guy who she ends up seeing on and off for the next/past year. They basically just used each other for sex when they were drunk, which kind of upset her in the end, and was the reason why it ended. So moving on, like maybe two weeks ago, she goes out to the bar with on of my roommates (pretty normal, they’ve been friends longer than us), and when they come home he goes to bed and she comes and wakes me up (im literally sleeping) to come sleep in my bed. Not saying this isn’t normal, we’ve slept together in the same bed many times without hooking up, although, the last time maybe a couple weeks before we basically ended up spooning all night. (pretty gay right?) Lol. So anyways, she comes wakes me up, we end up making out for a bit and once again, its kinda weird for both of us. Long story short and despite the awkwardness, we end up having sex (which she pretty much instigated) but she stops me halfway through and we stop. Now, after the fact, the next morning/ next few days when we see each other, its like shit isn’t awkward or anything but we can both kinda sense things are different I guess. Now that being said, I have no fucking clue what this girl is looking for. This whole time I’ve been more or less indifferent towards her, she’s good enough looking, fun to chill with and so on but I never really had any desire to date her or go out of my way to bang her. Alright so here’s the kicker, the next day after we bang, I end up changing my sheets due to some other shit.. I probably wouldn’t have noticed since the top sheets black but underneath there is a small stain in the middle of the bed which definitely bears the appearance of period blood. Like this bed is 2 months old and im a virgin, where else are brownish/red stains showing up from? Pretty fucked up right? I mean I’m not grossed out enough to turn my dick in and call it a day, but I just thought it was a little fucked up that if she knew she was on her period she would do that, us being friends and so on, and I wasn’t even wearing a dome. But then again, she might not have known and that might have been why she told me to stop, in which case I wouldn’t really blame her, although I get the feeling most girls at this age know when that shits coming round. All this being said, I still want to have sex with her again as the first time was pretty weak, but I would also like to avoid getting dragged into any relationship, which I think she might be looking for. So I guess my question is, is there any way to go about this lightly or am I just waiting for it to blow up in my face? And should I let her know about the stain, which most likely, but could maybe not belong to her?

A few things before i get into the advice…
1)No virgin has ever “banged”. They get banged.
2)DO NOT TELL HER ABOUT THE BLOODSTAIN. That is very likely the reason she stopped and I’d guess she’s a little embarrassed about it. Also, sometimes when a girl is about to get her period, sex will initiate it. I’ve had that happen to me a few times with girls and , at first, you think you did something wrong but the you realize it’s just nature taking it’s course. So, it’s possible she didn’t know she had her period until you set it off.

Okay…So, from what you’ve told me, I get the feeling this girl is a typical college girl who, while out to have fun, is also not a whore and wants to be treated with some respect. Whether that means she needs to be someones girlfriend or just wants the guys she sleeps with to acknowledge her, I dunno. But , one thing is for sure, i don’t think she’s a fan of getting fucked one day and ignored the next. Not saying you did that, but I’m just putting that out there as the worst possible thing you could do to her in this situation.
Here’s the problem. You have no intention of wanting anything serious with her. You don’t know what her intentions are but you kinda assume that she’d want something more official with you than you’re willing to give. WELCOME TO BEING A SEXUALLY ACTIVE SINGLE MAN. The funny this is, you have no idea what’s going through her head. She may not want anything to do with you. She may just wanna cuddle and have sex on random drunk occasions. you really don’t know. The reality of it is, you’re at her will. Trust me, I know it’s easy to assume where a girls head is at but , unless you get some sort of verbal confirmation or overt signs,you’re just guessing. For all you know, she thought your virgin ass was terrible in bed. I mean, you were a virgin, there’s no way you did any real damage that night. My advice would be to talk to her honestly. This may backfire and mean you don’t get round 2 but , trust me when I tell you, it’s better that that you boning her again and shit blowing up in your face. You’re young. There will be more sluts in your life. Sluts who just wanna have sex and that’s that. If she is not that kind of girl, then let it go.
So, yeah, step to her like a man and carefully bring up the subject. You might be surprised with what you hear back.

You have mentioned a few times how your early 20’s self knew all the tricks to getting laid that your current self knows. I was wondering if you could elaborate on this. I think I know all the basics, but for me it seems to be mostly about timing, and if a girl happens to like some random things about me that I have no control over. It seems there is some pieces of the puzzle I am missing though. Break it down for me. The Blockhead approach from meeting a woman all the way to watching her do the walk of shame from your apartment window.

Damn man. I’ve been in a relationship so long I don’t even remember how to close the deal. There is no “blockhead method” cause if there was , it would be pretty faulty. The things I figured out were more subtle and might not apply to everyone. I was never a dude who went up to girl and started talking , then took them home that night. I was more of the “slow burn” type. You ever hear a pro athlete say how they started to figure things out when the game slowed down for them? It’s like that. When i was younger, I was obsessed with stats. I just wanted to get in, mark it down and keep it moving. At the same time, I was also so grateful for any girl who would let me in that i would fool myself into thinking i liked them more than I actually did. As I got older, I stopped rushing myself into trying to get ass all the time. I got more indifferent and , somehow, that got me more girls than being a horny puppy ever did.
Here are some things I sort of embraced at a certain age that seemed to work out for me:
1)Don’t sweat a girl super hard.
Acting like a groupie toward a girl only makes you look like a desperate loser. If you feel an overwhelming sense of desire for a girl, there are ways to channel that thirst into something slightly more appealing that fawning over them all the time.

2)Plant seeds
There is no rush in getting girls. Some dudes have a knack for bagging girls in a short period of time, others (like myself) were more comfortable just letting things take form over time. granted, this would often lead to girls liking me more than I liked them but that leads me to…

3)Be honest. All the time.
I dunno what clicked in my head but something happened around my mid 20’s where I figured out the most pure root to a drama-less life as a single dude was to just be honest. A lot of the bullshit that arises between single guys and girls comes from misunderstanding each others intentions. If you open up communication lines early about what exactly it is you have in mind, it makes everything go easier. Sure, there will be situations where one person will want one thing and the other will want something else, but at least you nipped it in the bud before getting strong armed into a situation you don’t particularly want to be in. While this type of honesty will lead to some missed sexual opportunities, it also opens doors for things like great booty call relationships with no guilt.

4)Girls like guys who are funny, confidant and who can listen
Simple really. If you’re not funny…well…I hope you’re good looking or don’t mind dating girls with shitty senses of humor. If you’re not confidant, that’s gonna lower your dating pool greatly as women can smell an insecure man from a mile away. Insecure dudes occasionally get lucky and land some hot girl who mistakes his insecurity for being aloof or nerdy but, in most cases, girls want to be with a man they know isn’t going to cry in bed with them.
As for the listening…duh. We all like being listened to. But , to many women , they’re so used to dudes tuning out the second they start talking that you’d be surprised how much the appreciate an actual open ear. Granted, this often will lead you to some of the most inane conversations known to man but, hey, take one for the team bro.

5)Play to your strengths
If you’re good with words, get comfy with texting/emails. If you’re more charming in person but have the text etiquette of a cro-magnon man, then talk on the phone. If you’re only charming when you’re drunk, meet her at a bar. Whatever it is you excel in, use it to your advantage.

Shit…I can’t remember anything else. I know i’m forgetting tons of things but, like I said, I’m a long way removed from being a single guy. Good luck though. We all need it.

7 thoughts on “Ask Dr. Tony Vol. 22

  1. Sorry Block, but you may be wrong. My first time, I wrecked the girl. I was definitely the dominant party and definitely “banged” the retarded dog shit out of her. There was blood and I thought for a minute that she might have been a virgin until the following morning my friend that picked me up from her house, who was a year or two older than I and went to college with her at the time, told me she was not a virgin(I was in high school still and was visiting him at the university). I asked her if she was on her period while having sex with her and she said “no” but then motioned that she was okay and to keep going. So maybe, I didn’t set anything off but tore it up so bad I caused some bleeding, which is much more likely considering things were so tight in there it hurt me to fuck her. At the time I thought she was abnormally tight, since then I’ve figured out I am just working with a thicker dick than most dudes. Maybe dude in the question actually beat it up pretty bad and is also endowed with more than she was ready for.

    • Shall I email your prize for best virgin fucker ever or can I have a home address to send the award to?
      Congrats on tearing up that girl the first time you had sex. You are in the 5% of dudes who didn’t bust mad quickly. Still, from the way you described it, it sounded like some truly awful sex. Just saying…

      As for the girl bleeding…it could have been any number of things. She might have even stopped him cause it hurt. Sure, maybe he had a big dick and fucked her all sloppily. Who knows? We’d need way more details and her side of the story to ever really know. But, I stand by my statement that virgins are terrible at sex. whether they last 2 seconds or 2 hours. You don’t get in a car for the first time and compete in Nascar races. Just cause you don’t drive off the road doesn’t mean that you’re not a shitty, wet behind the ears driver. that applies to both guys and girlss. It’s no ones fault. it just is how it is 99.9999999999999999999999999999999% of the time.

  2. I hate the slow burn if the guy isn’t interested. It makes everything really confusing. Quick question: I’m newly single and back in the dating saddle. I’m now dating guys in their 30’s and 40’s. And we go on dates. I can’t for the life of me figure out how long to wait to have sex with someone I actually like. Assuming we are super hot for each other, how long do I have to play the good girl? I don’t want a guy thinking I fuck everyone. Also if he’s texting me every day does that change the timing? I am super interested in this one guy I met last week but I’m used to idiot 27 year olds. We have already gotten semi-naked but that was on the first date. Sigh. Maybe there were too many margaritas involved. He was super respectful but stayed over that night.(no oral just lots of making out) I have heard from him every day since. I’m just worried that after that first date it’s going to be difficult to slow it down a little. And I am worried he thinks I am a whore. HELP!! When can I bone this guy and not have him think I’m a slutola???? Ps should I let him win in words with friends?

  3. Dr. Tony!
    I could use some help in regards to first dates. I’ve always been kinda socially awkward and dates make me extremely nervous because of that. I’m pretty good when it comes to flirting via text but in person, I can get a little shy.
    I recently met a guy, exchanged phone numbers, and have been texting him for several days now. He has just asked me out on an official dinner date for next weekend. While I am super excited, I am also clueless. Not only am I socially awkward, but I broke off a 4 year relationship back in the spring. My former boyfriend was the only boyfriend that I’ve had thus far and we never had a “first date” per say, we just jumped right into everything. I took a dating hiatus for several months after the breakup and then the two dates I went on after that have been with guys that I just felt no spark with. I’m hoping that this date will go well but having minimal dating experience (I’m in college), and being socially awkward, I could use some advice. Do you have any go-to topics to chat about to keep the conversation flowing and to avoid awkward scilences? Should I dress up or wear my everyday attire?Were there ever “deal breaker” type thingsthat you looked for on a first date that would rule out the chick’s chances for a second date? Finally, if all goes well, how many dates would you say is a good idea to wait before sleeping with someone? All of my guy friends say to not sleep together on the first date. In general, any first date tips and words of encouragement would be appreciated!
    Sincerely, Socially Awkward Girl.

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