Ask Dr. Tony Vol. 28

Back again with that sage advice you all desire, with half the calories and logic.
I’m not a professional but I am honest and I do enjoy hearing about other peoples problems. So, if you have a problem of the heart that you need some advice on, I’m your guy. I won’t fix you, but I’ll at least give you some perspective from a person who doesn’t know you or really care about you.
If this type of thing interests you, send me your questions. Email me at or leave the question in the comment section below. Both ways work wonderfully.
This weeks batch has a few abstract/basic questions. But it wouldn’t be an “ask Dr. Tony” without at least one meandering novella. I guess you could say, this week HAS IT ALL!


I could really use some help with my love life. I’m 18 and I’m about to enlist in the Army. I broke up with a girl that was 16 about five months ago (I’m still a virgin). This girl and I don’t have very much in common; I like your music, alt rock, classic hip hop, she likes One Direction and Daddy Yankee. She reads People magazine, I read Ernest Hemingway and Nietzsche. Only thing is, she still likes me in “that way” (DTF), she’s probably a good 8.5/10, and I’m a pretty shy guy.

My question is this: should I keep writing to this girl, wait two years, be good to go on leave and run the risk of being a manipulative bastard and enormous regret? Or should I just call it off once and for all and run the risk of being a virgin until I go to college at 22/losing my V-card in a seedy Korean strip club?

I kinda get the feeling , no matter what you do, this one is out of your hands. You’re going away for two years. She’s a hot young girl who probably twerks on youtube to Daddy Yankee. I’m pretty sure she’s not gonna wait around for you. I’d maybe see a point if you had a connection or even liked her (which it doesn’t sound like you do) but, even then, you’re far too young to be holding on to something this frail.
You virginity will eventually be no more and , though I understand the desire to want to get that out of the way, putting all your eggs in her basket is just setting yourself up for a disaster. You might come back from duty to see her pregnant for all you know. And you are not the father, bro,
That said, there’s nothing wrong with staying in touch. You never know. It could pan out and you might one day, in fact, hit it. But do not put an iota of emotional worth into it. Just keep reminding yourself that while you’re out there serving the country, she’s very likely blowing some dude who bar tends at a TGIFridays or works at an auto parts dealership.

Why do so many people seem to reserve the most unfeigned positions of their hearts for people who truly despise them?

Is this a Taylor swift lyric? Perhaps something Jared Leto once wrote? Whatever the case, abstract question, dude.
People just want to be accepted. As much as we all say “I don’t give a fuck”, sadly, most of us do. Deeply. So, when you meet someone that you can tell isn’t giving you the respect you deserve and/or are giving to them, one of two things happens.
1)You immediately hate that person and want to fight them/never talk to them again.
2)You cannot understand why this person doesn’t love you, cause you’re so fucking lovable, and you go our of your way to try and make this person like you. Even though, this person could not care less.

In terms of applying this romance , the desire to be loved it strong. It’s the same reason a girl will sleep with some creep she met at a bar and “had a connection with” then make up all these false realities in her head about them, only to be devastated when he never calls her and/or forgets her name. Some people are just more willing to throw their heart into the ring. unfortunately for those people, they have a knack for finding people who are unavailable and have no interest in stepping into the ring in the first place.
Clearly, this question comes from a place of heartbreak (and possibly a girls journal with a tiny lock on it cause her brother keeps trying to read it to his friends). So, to this person, I say just hold your head. Whatever that guy/girl did to you is par for the course of life. There will be more of this as life goes on but it does get easier every time. Heartbreaks and 808’s, amirite? KANYE knows what’s up.

I just slept with my ex today. I’m not sure how to feel about it. One part guilt, one part kinda wondering about us together, and one part wanting to tell her to fuck off next time. I’m not one to sleep with a lot of girls. Honestly, I only ever do in a relationship. We had a pretty bad break up. She’s a good bit younger than me and in college. I’m out on my own, have a job, and I’m actually looking at going BACK to college. She grew up in one of those tiny small towns where people live next to their parents until the parents die. Then they move into their house. Doesn’t help that apparently she’s got a reputation of being really immature for her age too…did I mention my mother taught her in high school?

Anyway, she liked to do things like blow up a small fight into something big. She would actually pretend to not be able to hear me and just close her eyes in the middle if she decided she was fed up. Hell, she even flat out punched me a few times which she, amazingly, thought was fine. Actually, she once told me that all of the blow ups were fine. Lot’s of really juvenile crap like that. Don’t get me wrong, I certainly had my screw ups during the relationship and it doesn’t help that I went through what might be the worst bout of depression in my life. It’s definitely not all on her. The last time she hit me, I hit a cinderblock wall and left big crack in it. I also had to have surgery on my hand. Obviously, I’ve done some stupid shit and no one is ever always right in a relationship. I’ve learned a lot from my mistakes and have owned up to them though. I actually feel a lot better about life in general since then.

Then we started talking about a week and a half ago. I’ve been straight with her that I don’t want to be in a relationship but, yeah, I definitely miss some things about the relationship and have some unresolved feelings about the whole thing. She says it’s all physical, then I get used as an emotional tampon or she calls me multiple times a day just to talk. Plus she throws herself at me. It’s like a bizarro version of the friend zone. My guess is she’s not really sure how to handle her own feelings. I believe she doesn’t want a relationship…mostly because she’s got some really big hangups about the past. I do too. That’s where the guilt comes in. I am older, and frankly I was fine without talking to her. I almost feel like I’m just doing more damage to her by continuing to respond and then sleeping with her today. The wondering about the relationship comes in because, if things have changed on her side as well, it could be a pretty awesome thing. We always clicked. The wanting to tell her to fuck off comes from the fact that she’s already gotten pissy about two things. One of which was minor and the other had absolutely nothing to do with me. She did apologize for being a jerk. Plus, it seems like she can’t just be straight with about what’s up and still has trouble seeing some of the jacked up stuff she did. Part of me says that I should keep this on the side to see how it turns out. Then another says I’m just being a dick to her and I don’t need that crap in my life to begin with.

I’m a guy that genuinely likes long term relationships. Ideally I’ll find some girl that I’ll end up spending the rest of my life with. I don’t want to screw with someone and just make stuff worse for them either. You’re my only hope Dr. Tony! I’m also the only guy she’s ever slept with…or had a long relationship with…

First off “The last time she hit me, I hit a cinderblock wall and left big crack in it.”
Bro, you the incredible hulk? You cracked a cinder block? Jesus fucking christ.

This is an easy one that I think you knew the answer to before you even finished writing the question, So, if you need my validation, I can do that.
Not cause she’s a crazy person. Not cause you’re in danger. Do it cause she is not the girl for you.
“We always clicked.”
The only thing that sound like it clicked was your lego like penis into her vagina.
You relationship and her sound like a nightmare. Sure, the sex now is nice but, as you said, you’re not really bout that casual sex life. I think, because of this, it will be easy for you to get caught up in it and eventually end up back with her. Granted, this would last a week and eventually shit the bed terribly because you two have no business being together.
“I don’t need that crap in my life to begin with.”
If this is a thought that goes through your head and you are a “one day i will meet the girl of my dreams and settle down” kinda dude, then that’s all you need to know.
But, beyond all the flares you sent up that your head isn’t in this, I tend to think that couples who are based in explosive fights are doomed from the get go. When it all is said and done, if you’re gonna be with someone , getting along with them like a civil adult is your priority. Some people feed off drama and , while it may fuel some awesome and hateful fuck sessions, that shit can only last but so long. Think of it this way: You’ve been with her. You know how that goes. No amount of maturing is gonna change her THAT much. Maybe a lobotomy but I’m assuming that’s off the table.
So, cut your losses and bow out as gracefully as you can. she will be sad and mad but it’s for the betterment of the entire rest of your life.

Dear blockhead,

My mother in law hates me and she is a doo doo head

I need advice on how not to blow up at her

I think the golden rule of dealing with in-laws is just that…deal with it. Perhaps it’s because I’m a fairly emotionless person but I don’t find it difficult to totally disconnect from these kind of issues.
You’re only job is to treat their daughter right and be polite. If that’s not enough for them, fuck’em. Still, you gotta be polite though. Just let whatever bullshit they throw your way roll off you cause, in reality, who cares what these people think? They aren’t your parents. Look at them as two (assuming they’re both alive) people you have to deal with a few times a year. Smile, nod, make small talk, tell them what they want to hear and that’s it. They throw shade at you, just take it. Cause, like I said, WHO CARES WHAT THEY THINK. Sometimes you gotta eat a little shit just to keep things civil. Let your wife worry about all that shit. It’s her crappy family, not yours.

13 thoughts on “Ask Dr. Tony Vol. 28

  1. i usually say fuck most people in life. out of 100 people you meet how many do you really like enough to hang with?

    • I don’t really hate many people. I only care about a small handful though. That said, I’m perfectly capable of hanging out with and enjoying the company of someone I don’t particularly “care” about. That’s why you should have different tiers of friends. ranging from casual acquaintances to close friends.

  2. I have only slept with my wife. Growing up, I was a total “sucker for love” kind of dude (mostly due to being strictly raised Catholic… thanks for that, parents!). Instead of realizing I was young and should have been smashing whoever I could, I was in a bunch of long-term relationships and full-on sex just didn’t really happen except with my wife. We dated on and off and she slept with other people because she was smart and took advantage of being a virile youth. We got back together eventually and things were awesome, so we got hitched.

    While I still want to use a time machine and go slap the shit out of my younger self for being a total pussy, I’ve come to terms with the fact that I’m probably only going to sleep with my wife for the rest of my life, and my relationship with her (and the sex) is cool enough for me to be OK with that. I knew this would be the reality before I decided to marry her. However, I am obviously still attracted to other girls. No plans to act on it at all (not going to screw up my good life now to get back at my idiot younger self), but I have a question:

    You’re a dude who seems to have done OK with a variety of different girls and you’re in what I assume to be a monogamous long-term relationship. Do you still have a big urge to bone a huge number of girls, or is that something that you’ve gotten out of your system? I guess I’m just trying to figure out what is human nature vs. regrets about wasted youth.

  3. “I’d maybe see a point if you had a connection or even liked her (which it doesn’t sound like you do) but, even then, you’re far too young to be holding on to something this frail.”

    “It’s the same reason a girl will sleep with some creep she met at a bar and “had a connection with” then make up all these false realities in her head about them, only to be devastated when he never calls her and/or forgets her name.”

    Two times in one post you mentioned “a connection.” Ask Dr. Tony lends itself to that, I understand. However, I am tired of hearing about this connection BS. It seems recently the idea has been trending, and well anyone who uses the term in relation to another person they’re involved with needs shaken baby syndrome.

    • While being slapped repeatedly*

      This isn’t Disney World, and you’re not electrical work or ethernet.

    • I mean, I’m not a sentimental or particularly romantic guy but “connections” do exist. It could just mean good chemistry with someone. You’ve never met a girl who you immediately just sort of clicked with? Like talking to them came easier than usual and you were comfortable right away? If not, i feel bad for you. I’m pretty just That’s kinda how good relationships start.

      • For sure I have, but the term “connection” rubs me the wrong way. I feel like calling it what it is, does whatever it is, more justice.

  4. I took my head out of my ass and dropped it a few days later. Interestingly enough, she’d gotten mad at me for something that a mutual friend did and had nothing to do with me. Hell, I even agreed with her on it. Anyway, I broke it off as she was telling me she wasn’t certain we should do it anymore…then got mad at me for it. I thought we were agreeing. Go figure.

    And I don’t take kindly to being punched because you were mad I didn’t talk to you on the phone while I was hanging out with friends. To be fair, the wall broke my hand a lot worse.

  5. Dear Dr. Tony,

    I’ve been hanging out with this girl that I like. How can I convince her to let me stick just the tip in to see what it feels like?

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