Ask Dr. Tony Vol. 24

Ahhhh yess…It’s time once again for the worlds foremost mind on the topic of love and dating to let you people know what’s up. Okay, maybe that last sentence is total bullshit but, still, I give honest advice and try to no sugar coat things for you like you’re reading this in Jane magazine or some shit.
I always need more questions so, if you’re struggling in love, need advice on your weird relationship or simply feel lost about the opposite sex, send me your questions. Leave them in the comment section below or, better yet, email them to me at I’m here to help.
Now, on to this weeks struggle.

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.

Man, dating is stupid. It puts all this extra pressure on people when the title “date” it strapped to what is essentially just two people hanging out. From the sound of things, you’re not really a “go out and get laid” type of girl so I’d venture to say you’re more traditional. So, really, “dates” are something you might wanna get used to. I think your issue is that , because you think you’re socially awkward, you’re over thinking the entire thing. Really, the pressure is more on the guy. He asked you out. It’s his job to charm you and make you feel comfortable. All you need to do is be there , be responsive and not sit there silently like a scarecrow with a vagina. If he is like most other breathing males he will want this date to go smoothly. That means he will do his best to avoid awkward silences. If he’s smart, he knows that means simply asking you questions as a means to steer the conversation. I have friends who can talk to anyone for hours about nothing simply by asking questions. It’s not that difficult and only goes wrong when the two people talking come to a disagreement point about a topic that makes them both recoil a little. “You love abortion? but i hate abortion!” and it’s all downhill from there.
However, this is a college dude and who knows less about dealing with women than a college dude? So, on the off chance the conversation lulls, I sometimes think it’s a good idea to throw caution to the wind and just address it. Not only will it speak on the elephant in the room but it may actually steer the conversation away from petty small talk into something a little more deep. often just facing insecurities head on is nice cause it gets it out of the way and relieves any stress that may have been there due to those feelings.
as for the other parts of the dates-
Dress code: Depends where you go (fancy restaurant means fancier clothes) but, again, you’re in college. He’s probably gonna take you to a place that serves chicken wings on wax paper. Just look cute. Men are simple. We don’t care about your shoes, handbags or earrings. Show of your body is a subtle way and make your face look like it you didn’t just wake up.
Deal breakers: That’s more of an individual thing. For example, while a deal breaker for me may be that the girl thinks the movie “party monster” changed her life, for you it might be that he didn’t use the proper fork for his salad. Both those things are petty but everyone has got their own issues. In this early stage, I’d say the deal breakers should be things like “he’s an asshole” or “he tries to finger you before the appetizers come out”.
When you should let him enter you: Again, there’s no set schedule for this. I would tend to agree with your male friends that fucking on the first date doesn’t bode well for long term relationships. So, if you see this dude as a possible father of your kids, make him wait a few dates. If , halfway through the date, you realize , while you’re attracted to him, he’s not really a long term type, fuck him right then and there on the table at the red lobster you’re eating at.
To close this out, I have a feeling your awkwardness is more in your head than anything. I say this cause you seem to have no trouble getting dates. I know some real awkward girls and they haven’t gotten asked on a date since the early 2000’s.So, you’re not as awkward as you think. You’re simply a girl in her early 20’s. There’s millions of you and I’m willing to bet 85%consider themselves awkward when, in fact, they’re just kinda normal.
Also, It sounds to me you’re just more of a “Relationship” type girl who wants to be treated respectfully. Nothing wrong with that. To be honest though, you’re in college. You should be getting sloppy and going home with dudes who’s name you don’t know from local bars. All that dating bullshit is for later in life. But, hey, to each his/her own.

So i’m dating this really cool girl from like a month and she’s beautiful,smart,has a great body…The problem is i started growing feelings for her and i dont think she feels the same about me. I dont think we are really connected., we are seeing each other 2 times a week but we talk daily on messenger. We go out on weekends and she sleeps at my place Saturday night. But last saturday she wasn’t in the mood for sex cause she said she isn’t feeling ok. Today,Wednesday,we were supposed hang out all afternoon but she had some problems to solve so we saw each other 1 hour. Today also told me she is thinking going to France to save money for master’s degree (we’re from Romania). I encourage her of course to folow her dreams and its not sure she will go at all. She is texting me every time she goes to sleep,so do i but maybe is only a routine for her,i dont know.
I wanna talk to her,tell her how i feel but something tells me thats not a good ideea,i dont wanna look too needy. We dont talk about our relationship at all,just kisses and small talk. So is there any chanse this is just how the way she is? not sentimental and stuff. Or she’s just not that into me and it won’t take long before she dumps me,what do you think Dr. Tony? 🙂

Sounds to me like you’re on the way out, bro. It sucks but it’s a reality. When a girl likes a dude, they’re rarely coy about it. especially after you’ve had sex with them. Not to mention , when you a have sex with a girl who likes you, they tend to want it again sooner than later. Even girls who have bad sex with a guy they like will take one for the team simply to be around that guy again. Also, this part: We had sex only once,she told me she liked it made me sad. It made me imagine you pulling of the condom and carefully placing it somewhere that you could later grab it and place it in a shrine, looking at her with doe eyes and asking if you did a good job. I’m hoping that’s not what happened but it certainly had an air of insecurity to it.
You also mentioned that you don’t have a connection with her so what’s the deal here? Are you just very attracted to her? Cause, how much can you really fall for someone you don’t have a connection with? That’s kinda how these things work. The connection is just as valuable as the attraction in the long run.
Regardless, it seems clear to me that you’re not going to be a permanent fixture in her life. You’re pretty low on her “To do” list already. My advice would be to milk her for as much sex as you can before she fully stops returning your texts…but I have a feeling it’s too late for that even.

so i dont know if this is the kind of love advice you dish out, you can even recatagorize it into answers for questions if you’d like

me and my girl have been dating 6 months, and for the most part everything is amazingly awesome. the problem is that when she drinks too much she wets the bed. my bed. the first time i kind of laughed it off and told her how cute it was while i stripped the bedsheets (which should have been her job in the first place). but now its been 5+ times. so probably at least once a month i wake up next to her wet and clammy and smelling like piss. she has a very small bladder she tells me, and she was supposed to get a surgery when she was a kid to fix it. so its not like its her fault per se. on a related note, she might sleep walk too. she’s come bursting into my room in the middle of the night asking why i left her on the couch in the front room before, and i was just bizarrely confused and told her that i was sleeping & i didnt know she was gone in the first place. so maybe she has sleep issues. the sleep walking doesnt seem to be severe as long as she doesnt hurt herself, but i just cant wake up soaked in piss anymore. i love her and im not going to dump her over something like this, but she gets upset when i tell her that she should go home at night and piss her own bed (in much nicer words of course). shes convinced that im using her bedwetting as an excuse to distance us from each other or so i dont have to spend time with her at night, but thats not the case at all. for your reference, ive asked her if she had this problem before we started dating and she said “no not often”, as opposed to “not since i was 5”, so i can only assume she pees the bed at home too and is kind of shy about telling me. also her room mate has told me she caught her sleep walking/trying to piss at the same time…. in the corner of her (the roommate’s) room. which makes me think maybe the bedwetting and sleep walking are all part of some bigger sleep issue where her body doesnt know its asleep or whatever. im not a scientist. and neither are you. but maybe you could give me some advice, yeah?

Man…that’s a messy situation. you must be pissed. AMIRITE?!?!!
Nah, but that does suck. She’s got problems that neither you nor I are fit to help her with. She’s obviously ashamed of herself. I mean, shit, she’s an adult that pisses the bed on the regular. The shittiest part is that it seems she’s made it so you can’t do anything about it under the guise of her thinking you want to “distance yourself from her”. That’s kinda putting you in a corner…and peeing on you, spiritually.
So, clearly, this problem is bigger than you and your relationship with her. Honestly, she needs professional help and has probably needed it for her entire adult life. I don’t know if you take her to a sleep specialist, a shrink, or a urologist…or all three…but it should be high on her to do list.
Also, if this only happens when she drinks perhaps she shouldn’t drink. Or just avoid her on nights she drinks. Just a thought. Worse case scenario , she gets wasted , goes home with some other dudes and pisses on his bed. I know that’s easier said than done but the next time she does drink just send her home. When she gets all pissy (in attitude) just tell her “Listen, this has nothing to do with my feelings towards you. I love you (or whatever) but I just don’t want to deal with cleaning up your piss with a hangover”. Obviously, that will go over terribly but she’s the one with the problem that needs to be addressed , not you. Maybe , like a piss soaked mattress, your words will one day sink in.

I have a question. This guy (32) has started staying over at my (34) house every night for the past week and a half. I don’t invite him and if he doesn’t call I don’t stress it or call him but infallibly he ends up calling and being like, hey can I come over him. I kind of like him so I say yes. He comes over and we cuddle and sleep (gayness). No messing around. I get naked because I sleep naked and I wouldn’t mind boning him. He sleeps with his arms around me. He keeps dropping lines like we should live together or maybe we should try dating. But I’ve told him that that would only work out for me if we were having sex. He is in his first year of residency as an OBGyn and is exhausted all the time not to mention he looks at pussy all day long. We have been friends for a couple of months but not intensely. He’s just all of a sudden become my bedmate?! Wtf is going on in this guys head??? At what point do I get the ween?? Is he just using me for some physical affection and my amazing bed? He was kind of dating one of the other residents (who is a virgin) but he seems to have just dropped her. I’ve encourage him to continue to pursue her since she’s a virgin and he doesn’t feel like fucking so it seems like a good match. Not to mention they are both republican. On the other hand if he would start givin me the dick I’d be open to a relationship with him. We are rather, how u say, sympatico. Maybe he just likes playing with my boobs. I just want some insight into his mind plz. Maybe I’m being too much of a man about this. I’m not looking to fuck right away but some making out would lead me to think that something might happen at some point?!?!

Never say “I’m being too much of a man about this” when discussing dudes. Cause, if all girls were “too much of a man” about matters like this, men and women would get along much better. You’re entitled to want to get laid. It’s you’re god (or whoever) given right. This dude sounds like a weird virgin. Any grown man who still fascinated with simply playing with boobs has some sort of stunted sexual issues. Boobs are great but if you’re in bed with a naked girl on multiple nights and that’s all you’re doing?
Dude sounds like he has an inverted penis or something.
I can’t really give you insight on his mind cause it doesn’t make sense to me. Unless he’s a bible loving republican who believes in no sex until marriage , than none of this makes sense to me. He just sounds like a homeless dude with the mind of a grifter. Does he have home? Why doesn’t he ever go there? The fact he’s in school to be an OBGYN is even crazier. He should know his way around a vagina.
Anyway, the whole thing is fishy to me. My advice to you would be to rape him. Start sucking him off, that’s usually a good way to get a dudes attention and then just take it from there. Have you never gone for his junk? Whatever the case, that power move will bring everything to a head (no pun intended).
In all honesty, I don’t think you wanna date this guy cause he sounds like a fucking loser. but i do believe that your curiosity is eating you alive. The fact he’s in his 30’s makes this even stranger. Basically, stop letting this dude crash at your house unless he’s willing to give up the goods. You’re not a fucking bed and breakfast. If what you want is some peen, then let it be known beyond a shadow of a doubt. If it turns out he’s a 32 year old virgin who’s waiting for a ring, at least you’ll find out.
Also, am i crazy or did I answer this exact question somewhere else on my blog recently? I’m have a strange case of deja vu…

12 thoughts on “Ask Dr. Tony Vol. 24

  1. This has been the best one in weeks, Block having a great time with the puns,

    “All you need to do is be there , be responsive and not sit there silently like a scarecrow with a vagina”

    That had me laughing so hard, hah

  2. I have one more for the doctor!

    first of all, excuse my bad english… I hope you understand everything!!

    the story is very long but I’ll keep it short and try to make more a “global question”

    I had this girlfriend for like 7 months but it’s over (she left me). Our relationship was awesome, like good friends too, it wasn’t only attraction, so I’m not mad at her or anything and I’m really up to being friends (seriously) cause we like similar things and we always talk lots about music and I love to hear her opinions about my artworks etc…

    anyway, It seemed that it could work but I’m not sure anymore because sometimes I feel angry when she doesn’t text me back or shit like this. It is fucking stupid but I can’t control it. Sometimes I’m not sure if she really wants to talk to me and she just does it because she doesn’t want to hurt me or anything

    I’m confused because I’ve been with a few (5+) girls since she left me 5 months ago, but somehow I guess I want to be friends with her cause I still like her… but I will always feel something for her, right?

    so, what’s your opinion on being friends with an ex-girlfriend? bad idea? will be always stressing?
    should I just move on and accept that she is not part of my life anymore?

    I feel sad about losing someone who I like (not just because she is a girl and hot) but maybe I’m just a fucking hippy

  3. I recently asked if a guys seemingly indifferent mood while in his girls presence was indication of him maybe starting to get bored of her. She stays at his place at least two to three times a week. Instead of him being willing to stay at her place for one of those nights, he’d rather go stay at his (dirty) house where he might have his own bed and musical instruments, but no model-pretty girlfriend (beautiful model- like iabelli fontana, or Jacquelyn jablonski.) Whom he says he loves cause he left her at her house alone. Also, he had a difficult time the other night getting and staying hard when she was really into it and wanted him, but he “was caught off gard ” and “wasn’t into it at first “. He seems very honest and like he does love her but something doesn’t seem or feel right..

  4. It’s hilarious to think about some guy saying “I have to look at vagina all day… When I get off from work, I just want to come home, drink a beer, and cuddle.” LOL

    The only other thing I might guess is maybe he has easy access to prescription drugs like oxycontin while doing his residency, and is so fucked up all the time he has no sex drive. Dr. Drew taught me that shit.

    • If he’s doing oxy all the time he’d probably feel good enough to want to have sex..a lot-and champ that shit out nonetheless. Unless he’s doing raw heroin he probably wouldn’t have that problem..but who knows? no hate on your comment just giving my two cents. This edition was great.

  5. Hey! So I was dating this guy for about 8 months. Everything was going really great, getting pretty serious and I was really in love with him. Suddenly though, he started to get more distant and ended up breaking up with me. He definitely has some weird commitment issues… not just in our relationship but with his friends, school, work, etc. We had talked about it before when he disappeared one week and I found out he went to San Francisco and forgot to mention it. I’m really not a clingy person so it’s strange to me that he felt a little smothered. Anyway, after we broke up (about two months ago) he really wanted to stay friends. At first I was really against it but a few weeks ago I decided to try it. He came over to our mutual friends house to hang out and drink and everything was going well. We all ended up on the couch watching James and the Giant Peach (great movie) and he was extremely cuddly. It led to sex and the next night he called wanting to clear things up. I knew it didn’t mean he wanted to get back together or anything and that it just kind of happened but he kept saying how much he missed me and how seeing me took him back to when we were together,with that a ton of touchy feely mixed signals leaving me sooo confused. Do you think he’s just confused or just wants to get laid? I made it clear I wasn’t going to do the friends with benefits thing… that it was a relationship, just friends or nothing but he still wants to hang out with me… any insight?

  6. Here’s a few questions for answers, admittedly the last one is kinda lame by comparison, but maybe you’ve got some wisdom into the magic that is cheese. (also, clearly i’m not looking for some wikipedia type knowledge on the history of the hotdog or milk, just for you to rewrite history as you think it went down):

    “Was the dude who made the first Hotdog also the first one to try a Hotdog, or did he make somebody else take that first bite?”

    “Was the first sip of cow milk an accident, a perverted motherfucker, or the results of a lost bet?”

    “Why is cheese so fucking god damned good? Aside from Blue Cheeses, I’ve never met a cheese that was bad. Granted they’re not all mind blowers, but even a not-that-great cheese is still consistently better tasting than any other not-that-great option of normally good food.”

  7. Im with the second question and yeah we broke up,she was hot,i was super atracted to her but she told me im not that confident and dont have many passions and that was frustrating for me to hear knowing its not true. I tried to tell her but it was too late. At least we had more sex and that was fun. thx bro

  8. The OBGYN question was in the comments of the last answers for questions. You basically gave the same advice: blow the dude or kick him on the curb. You’re consistent, Block. Also, just wtf. ‘I am a pussy doctor… but I don’t want your pussy.’ Sounds like a Dr. Evil line.

  9. seems that male OBGYN’s have no sex drive so LADIES STOP CHILLN WITH DUDE OBGYN’s IF YOU WANT SOME DICK lol b/c the same issue was in your last vol. too……

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