Ask Dr. Tony Vol. 30

What up everyone,
It’s time once again for me to give you my un-professional advice about your screwed up love lives. As always, I’m not a licensed anything but I do feel I can shoot from the hip and shed some light on most problems in the arena of love and relationships. I always need more questions so please don’t hesitate to send them to me. Everything is anonymous so this is a safe place. Send those questions to: or leave them in the comments below. That is also anonymous.
Oh and , by the way, I was thinking it would be cool to hear back from past question askers. Basically, a “where are they now” that shows how wrong/right my advice was. If you have written in before and asked a question that I answered, I’d love to hear back from you and see how it all turned out. All I ask is that you maybe just tell me what volume of “ask dr. Tony” I answered the question in so I can connect the dots and have it all make sense when I repost the old questions with the new updates. So, yeah…let’s hear some of those. Even if there is a risk of this exposing how bullshit my advice really is. I’m willing to take that chance.
Anyhow, here are this weeks questions:

Hey block.. I have a problem with my bf that I can sum up..he simply doesn’t trust me and I really have no idea why or what is it that I do exactly. Ive never lied to him before, but im quite an introverted person which he views as being mysterious and shady.he always tells me that trust should be earned and it isnt something that exists just like that. But I often find myself explaining myself on stupid things like why I didn’t answer the phone in the same minute I got a phone call from him or why my surrounding is quite when im out with friends..I constantly try to earn, try to explain and try to do what he wants. But no luck, this same cycle is repeating itself over and over. I know trust is the basis to any relationship. But is there any hope in here? Why is he doing that? I often mess with my own mind and cant believe hes actually like this and start thinking maybe I am the problem and dont even realize it. Would love your feedback. Thanx

Sounds to me like you’re cheating, you heartless bitch. Just kidding.
Clearly, this is all this dudes problem. He’s either highly insecure or has a history of dating girls who cheat on him or both of those things. Unless you’re omitting some very important details (things like “you’ve cheated on him before” or “when you get drunk, you get extremely flirty in a careless way” or “in the past, you have cheated and he knows it”) then I can only assume this is 100% his issue. Sounds to me like lil’ dick problems, to be honest.
I’m assuming this relationship is somewhat new cause , in most cases, if a relationship is shrouded in jealousy, it doesn’t last long. So, yeah, this one is going down the drain soon. He’s not gonna get better. You either have trust or you don’t. Tell him to go date a nun who had a hysterectomy or something cause he sounds like that may just be his personality type.

On the other side of things, if you did leave out some crucial details to why he is acting this way that point the finger at you a little more, trust is not something easily won back. In fact, I’m a believer that most people never really trust someone who’s given them reason not to. So, you know, just be honest with yourself about why he may feel this way. But , if you’ve really given him no reason to act this way, get out of that relationship as soon as possible and let him be some other poor girls problem.

So in a lot of your answers to questions you make reference to “If only I knew then what I know now” when it comes to dealing with the ladies and all the poon you missed out on. To those of us still stuck in the not knowing phase, what advice would you have? What is it exactly that you now know?

What I know is what every guy who reaches a certain age knows…when you’re young, you’re high strung. both emotionally and sexually. Everything matters intensely and that stops a lot of people from just stepping back and looking at things in a more relaxed manner. Basically, you care too much about stuff that , in the larger scheme of things, doesn’t really matter. It’s mostly youthful insecurity and not really understanding human interactions. We all get more socially tuned as we get older. Granted, some people become mole like in their social lives but that’s mostly cause they don’t like what they see and want to avoid it all costs. But, still, even with those types, there is a particular kind of wisdom they have that comes with growing older.
The other day I was having a talk with a friend. He recently broke up with his girlfriend and now he’s back on the scene. He’s my age but tends to be around lots of younger girls (early/mid 20’s). We discussed that how, at this point our lives, talking to a 24 year old girl is really easy. Mostly cause we’ve been through more things and literally know more than them. If a 35 year old guy has designs on a 24 year old girl, you attack that from a totally different angle that someone her own age. They is no urgency and they hide their thirst way better. Cause we learn that, in reality, it’s not that big of a deal. It happens. It doesn’t happen. The “I could take or leave it” brand of talking to women is shockingly effective. This translates to dealing with women of all ages. When you’re a real adult (I’m not talking about a technical adult) you approach situations as one. There’s no advice I can really give you that will turn your college party ass game into an air tight pussy getting machine. That’s not how it works. That’s the kinda thing you either have or don’t. I’ve met plenty of young dudes who have no problem getting girls. But the difference between that and simply getting older is pretty big. I don’t know what it is. A certain serenity washes over you and you just get more comfortable in your own skin. Most people in their early and mid 20’s spend that time still figuring our who they are and what they’re about. But the time you reach 30, that starts to be much clearer. And that clarity reflects on everything you do. So, even though those young dudes may be bagging girls at an incredible rate, they’re still pretty much flying by the seat of their pants.
The whole “If I knew then what I knew now” mind set comes from an impossible place. Sure, if my 36 year old brain popped into my 18 year old head, I’d get an unbelievable amount of vagina. but that’s cause I’d be dealing with the minds of children while I had the mind of an adult. It would be creepy. The fact of the matter is, there’s no short list of things I could tell you that will change how you act. That’s just your age.
So, my advice? Get older, bro.

I’ll try to make this short, but no promises. It may be a more ‘Dr. tony’ question but here it is.
My ex and I dated for 2 years, after courting her for about 8 months. I wasn’t the best boyfriend, I was a serious drug addict and it affected our relationship because she want to do what I was doing. It didn’t end terrible but it wasn’t even close to ok. Three months before we broke up, she dropped the bomb that she was moving to England. I’d already looked at rings, and I thought my search was done. When she dropped the bomb, my drinking and drug use went out of control. When I was sober I could understand, she was going to see family she had never seen and I was determined to make the best out of our time together. But then I would get real fucked up and be the biggest dick ever, I almost couldn’t help it, it felt like she was leaving me behind and it meant nothing to her. Granted if I was sober I could have. But I wasn’t and my actions were my actions. It’s been two years since she left, and since then I had only fucked girls until they wanted something more and then I moved on. About four months ago I got to the point where i thought i could dat again. And about 3 months after that i saw this girl at a bar I frequent about 4 times a week, more or less. We got introduced by a mutual friend that night. I got her number but I’m the worst texter in the world, so I found out through mutual friends where she goes. So I went to her bar and she was the first person I saw and we talked for forever and she invited me and my friend to her place afterwards. So of course we went. And we stayed up till 8 in the morning just talking and then went to sleep together. No sex, no anything, just sleep. We have been seeing each other 5 nights a week ever since, and the encounter at her bar was about a month ago. The funny thing is, I made her wait to have sex. She wanted it bad, but I told her I didn’t want to complicate things so early. I really liked her and in all my experience sex makes things complicated. I wasn’t able to hold out long, but I wanted to know her better before sex was introduced, so I succeeded in that. 11 days of constant hanging out, and me telling her it wasn’t time before it happened. I’ll throw in that I don’t do drugs anymore, just drink and occasionally smoke weed. I really like her, she’s 3 years older and I feel like I’m in a good place to be there for her. I had forgotten what it felt like to be happy, and she blows my mind everyday. I guess if there is a question in all of this I just want to hear your sage advice. I know you don’t know it all and it’s kinda hard to explain but I’m finally in a place where I feel comfortable being myself around her, we are both extremely honest with each other, and I care about her alot. I can’t drop love in there cause its way too early, but she makes me feel like me again. And it’s been years since I felt like this. I just want to hear your opinion. Thanks man.

Umm…Thanks for not making this long.
I’m kinda confused as to why you even wrote me this. Sounds like you want a pat on the back for making a girl you like wait to have sex. Congrats! You win the “I made a girl wait 11 days to have sex prize”.
My opinion on this is it sounds like cycle of all human relationships with added drugs in the past. That sucks what happened with your ex who moved to England but, hey, things happen. People come in and out of each others lives all the time. All you can do is chalk up those kinda things as fond/terrible memories/experiences and move on. As for the new girl, sounds like you like her. My only thoughts on this are that you need to remain off drugs if you want any relationship to work. I don’t know what kinda drunk you are but most people who go to bars 5 days a week are alcoholics. So, just saying, you might wanna get that in check. Especially if she is there with you. Sounds like two co-dependant drunks in love. Which is fine until it isn’t. Basically, just be careful. Make sure the thing bonding you two isn’t just your similar lifestyles and your place in life cause there are few things more depressing than a couple of drunk assholes in love. Well, cokeheads in love are pretty terrible too.

Dr. Tony,
Sorry, like most of these damn posts, this will probably be lengthy.Ok, so, I wanna fuck my boss. I mean, I have this hugely inappropriate crush on him. We are close in age (In our 20s) and he has all of the criteria that I look for in a man. I’ve been single for over a year and haven’t been interested in many guys, but my boss just has this “it” factor. I’m not even sure if “boss” is the correct term by the way, but he’s superior to me at work anyway. Now, I wanna point out that this isn’t a gold-digging slut type of thing, people in our office aren’t raking in that much cash. Also, for reference, this is a professional office not some, like, Pizza Hut, in which case I’d be way more inclined to pursue my boss. From what I’m told though, there is no “official” rule about dating within the office but it’s just one of those unspoken, sorta taboo things.
My problem is that I can’t decide whether it’s okay to attempt to pursue or if I should just try to let the “crush” pass. Man, I hate using the word crush, it makes me feel like I’m in middle school. Anyway, if it’s truly a lost cause then I could really use advice on how to get over the crush so I’m not fantasizing what he looks like naked anymore while I’m at work.
He’s fairly new to the office so I suppose it’s a fair statement to say we are still getting to know each other as co-workers…but I really do like the person that he is for whatever it’s worth. Occasionally, I feel as if he may find me attractive. He’s definitely stared at my tits before, he smiles every time I walk into the room, when I asked for his phone number he gave it to me without me even explaining it was for in case there was a work issue (I haven’t contacted him out of work though and he just could have easily assumed I meant for work stuff), and, in general, he’s just extremely nice with me. I understand he could easily just be a friendly guy, though.
I’ve always been under the impression, though, that if a guy is into you then shit like being your boss, doesn’t get in the way. However, I could be misinformed considering the majority of guys that ask me out are usually cocky assholes at the bar. I guess this is a whole new ball game for me and so I’m really not sure what to think but it’s driving me crazy how much I like him.
He doesn’t know that I like him at this point. I’m always friendly with him and I might accidently stare at him when I’m thinking of what he looks like naked at work, but I’ve never made any major moves. I’m not the best at flirting anyway and so I wouldn’t be surprised if he hasn’t caught on to my weak attempts at hinting that I kinda have a thing for him. Literally, I just kinda smile at him a lot and I’ve touched him on the shoulder a couple times when making a passing comment in a conversation…which in my mind is supposed to be cute or some shit. I texted him once about work, asking about a project and then thanking him for helping me on a project the night before. When I thanked him I also told him that he looked nice that night but he completely ignored that part of the text when he replied. I was like DENIED…but I realize it was a half-ass excuse for flirting to start with.
Now, like a typical woman, I’ve come up with a few reason why he hasn’t been flirting with me. Perhaps you can tell me if any of these reasons are valid. Honestly though, I fully admit that he probably just has no intention of flirting with me and I’ll eventually have to just get over the crush, haha, but anyway…first off, of course, he’s my boss. As stated before, it’s “taboo” within the office so perhaps he doesn’t want to risk that, plus it’s a risk in general dating someone you work with in case it doesn’t work out. Second, as I also stated, he hasn’t been at the office very long. Being that we haven’t known each other for that long, perhaps he wants to see the kind of person I am more, first. Also, he could easily think that I have no interest in him because I haven’t been explicit on how I feel. I’ve also thought that maybe he’s just a pussy. He doesn’t have any kind of “agressor” type personality. He gives off a little bit of a nerdy vibe, but in a cute way to me. Finally, our office is contractual, we work on this project until November when it’s over. He’s living here for the project so he may not stay past November and perhaps that’s why he’d not be interested in starting up anything right now. Most likely though, he probably just sees me as another co-worker. I get that, but a girl can dream.
I’ve thought about asking him to get a drink or something, since he’s from out of town and doesn’t know the area…so I thought I could lead with that as sorta a “you-don’t-know-anyone-here-or-what-there-is-to-do-here” type thing, but I’m definitely too scared to actually ask. Being rejected would, of course, suck. So, where I could use help from you is, first off, just general insight on the situation. Second, if this is a lost cause, do you have suggestions of how to get over the crush? Finally, if it’s worth any kind of shot, what would be a better way to flirt-with or approach him? I’m not a bad looking girl but, being that I’m fairly young and have only had one long relationship (4 years), within the past year of being single I’ve realized that I have zero game. Please help! Thanks, Block!

Man, that could have literally been one paragraph long and I’d give you the same answer. Brevity, people!

Reasons why he might not be into this:
1)He’s taken (is that possible? it’s funny that that is the one thing you failed to imagine as a reality)
2)He doesn’t shit where he eats
3)He’s not into you like that
4)He’s not trying to rock the boat at work and make anything weird for the future

It could be one or all of those things. The only interesting point about this all is that you said your job in contractual. The whole idea of coming to a strange city, working a few months and then bouncing seems like a perfect storm for a hook up. It also makes things easy for you cause, if it does’t go well, then he’s leaving soon anyway and the embarrassment will be brief. The way I see it, you have very little to lose if you are proactive at the right time. Your “Take him out for a drink” idea is fine. A little social lubrication never hurt anyone and I’m sure your overt flirting game will be pretty transparent to him and he will react accordingly.
One thing though, do you want to date this dude or just have sex with him? Cause if you have deeper feelings and think you wanna take this farther, then I’d say don’t even bother. He’s not gonna be there permanently so you’re pretty much just setting yourself up for disappointment. This can really only work as a sexual thing.
So, if it turns out he’s not into you…life goes on. Hopefully no one at work saw it happen but whatever. You’re young. You will recover.
As far as getting over a crush…that’s kinda like getting over a cold. As much as I could fill your head with bullshit home remedies, the only thing that really fixes that (or any emotion really) is time. The cool thing about unanswered crushes is that they always leave the door open a little so it’s something you can think about forever but not in a wistful way. Perhaps you’ll meet this dude again down the line in life and things will work out. With a crush, that could happen. But , if you’re a person who’d rather know the cold facts, I’d say you gotta take the reins a little. Just remember, as a girl, your “game” isn’t that important. You just have to send out some subtle clues to the dude and, if he’s interested, he will likely pick up on them. If he’s one of those shy guys, it’ll be harder and you will have to be less subtle but, in the end, if he’s in to you, he’ll help it happen in some fashion.
One last thing, when he didn’t respond to your flirty text that was one of two things:
1)He was being professional.
2)he’s not interested.

In both cases, I gotta say, that was not a positive outcome for you as both those reasons point to a dead end. That small detail makes me think he’s not into it but, hey, I could be totally wrong.

6 thoughts on “Ask Dr. Tony Vol. 30

  1. —>The “I could take or leave it” brand of talking to women is shockingly effective.

    Effective, but not shocking. Huge generalizations here, but, lots of dudes confuse your above statement with acting like a glib asshole. That’s not what this is. When guys pull off this brand, they are mirroring the girl’s process of decision-making, without even realizing it. Beyond that initial level of attraction, women absorb little bits of info as we go along in order to decide. So if you mirror that (even though you 100% already know you wanna be w her), it comes across as you enjoying the experience of talking with her, independent of your end-goal. This is disarming/intriguing and makes her feel that this is a guy who realizes girls are actual people too (even the ones he’s thirsty for). Feels way more authentic and less cheesy than other angles.

    • That, or maybe it just appeals to their primitive desire to be wanted by everybody. If you don’t show particular interest in a girl then she’ll work harder to get your attention. In my personal experience, initially being a dick (or at least acting indifferent to the girl) seems to work more often and more effectively than being the outgoing nice guy who enjoys talking to her and is totally involved in the conversation.

      • So difficult to respond to! But I will give it a NOVEL-SIZED sunday try:

        -Nah, you ARE right. W/o realizing, was speaking to my current situation (when 2 ppl, who have both dated around, seem to click w/o any pretense. Feels so much more comfortable/easy than all the other times. That’s how many good relationships start imo)

        -However, we’re talking about angling for fucking here! If I’m honest n go thru that list, yup 2/3 of guys were effective by being a little bit (or a lot like) an asshole.

        -PRIMITIVE DESIRE TO BE WANTED BY EVERYONE: yes, 100% true!!! (Why is that? Just biology’s way of ensuring that the womb is open to the fittest DNA available?) I know you’re right bc – 1) a lot of those guys weren’t ones I actually liked. Rather, they were complete opposites to me and I was curious to see if my non-alpha/soft power would have any influence on them. 2) I’ve thought about crossing that age threshold a lot. While I think it would be somewhat AWESOME in many ways, I’m also anxious about how being outside that “wanted/fertile pool” will affect my sense of self.

        -Therefore, bit of asshole? Effective. The problem though, is that if you keep doing it successfully to same way, eventually you’re going to get BURNED…HARD. I would like any guy 35years+ who has been single 50%+ of the last 10 years to tell me I’m wrong! That 2/3 of guys I talked about? I don’t see them as guys who angled asshole-lingly, I view them as actual ASSHOLES, past and present. I have no idea if they are (and I’m not saying I burned them)…but, whereas, a guy’s first/lasting impression is physical appearance…perhaps, a girl’s first/lasting impression of a guy is how he handled his thirst w/in that initial approach.

        -In other words, a guy’s thirst is a given in the situation! So, we inherently try to fit our own puzzle pieces together in assessing your true character. If you use the asshole method on a girl and it works…but you end up developing deeper feelings for her…this is when you will get burned. Because even if you change your behavior once you get to know her, that initial way you approached her will be ironed into her memory and she might not think of you as anything more suitable to her than a casual whatever.

        -People have to remember that this dance is an IONIC BOND between men and women, women are not a flat wall to bounce approaches off of. Don’t forget that she has her own manipulative intentions in playing the asshole game. Thus, I’m not saying that guys are the only ones who get burned in this situation, girls’ manipulative efforts burn them too, but in a much different way [can’t write anymore to elaborate on that 🙂 ]

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