Ask Dr. Tony Volume 5

Good day to all of you. The Doctor is in. Still here, giving unwarranted advice about situations I know next to nothing about. This week includes a question so fucking long , I was almost not gonna use it. However, it covers territory that I feel is quite relatable to pretty much every girl ever who’s dated a lazy guy who doesn’t give a shit.
Please send my more personal problems/questions at
It’s always anonymous and my advice is usually as spot on as it can be , considering I don’t know you or the people you’re talking about.
anyway, on with the session…

What’s your stance on workplace dating? i’m digging this girl I work
with – BUT she’s just freelancing – so the plan is to wait it out
until her (indefinite) freelance is up, so i get the date minus the
workplace dramas. I’m getting increasingly impatient though. Should i
just go for it or wait it out?

I think Workplace dating depends. Some people can handle it. Some can’t. It also depends on the intentions of both the people. In order for it to work, you must both be on the same page. If she just wants to fuck once in a while and you’re in love, it’s not gonna work. Not only just that , it’s gonna be a mess.
I was talking to a friend about this the other day. Jobs are one place where it seems like the playing fields even. Whenever I see a terrible looking dude with an attractive girl, I assume he’s either rich or worked at a job with her for years. It’s that thing where, when you see people every day, you lose perspective on how they actually look and begin to base your view of them on their actual personality. This leads to people hooking up who would probably not even look at each other in an actual casual social setting. I’ve certainly pined for 5’s that I’ve worked with , only to realize years later that the girl was in fact, mediocre in every way. It’s just how working closely with people works. You find ways to be attracted to what’s in your close proximity.

But i digress, your situation is slightly different cause the girl is a temp. I’d say by all means , go for it. Worst case, she rejects you, things are awkward for a few weeks and she vanishes. However, I only give this advice assuming you’re not a vindictive asshole. If she does reject you or you guy hang out and it doesn’t work, you gotta back the fuck off and not be a creep about it. OR, if you do get with her, fuck her and decide you’re not into it, you gotta handle that delicately. Basically, it’s all on you and how you act to make this thing work on any level. So, yeah, don’t be a dipshit.

Dear Blockhead,

I was in a relationship with my boyfriend (now ex-boyfriend) for almost three years. I tried to be happy with him but I always felt like something was missing. But being a typical girl, I convinced myself that I was content and ran the thought out of my mind. Obviously I was never able to escape it. Don’t get me wrong, he is a wonderful and kind person, we share many of the same interests, humor, and are content doing nothing together. But it seemed like that was the extent of our relationship. I have always been an ambitious person. I love to travel, go on adventures, try new things, and I am constantly going back to school. That is where we differ the most. He smokes a lot of weed, doesn’t have a driver’s license, no passport, an unsteady job and plays a lot of videogames. I would say he is a meat and potatoes type of guy, not easily open to trying new things at all. Communication is another aspect that we were never able to agree upon. I am a very open, emotionally driven individual and I can’t just bottle of my feelings. If there is something I am concerned about, I put it on the table so we can talk about it and hopefully work it out. He is the total opposite. He gets frustrated easily, brushes important problems under the carpet, and accuses me of ‘being negative’, ‘bitching’, or ‘nagging’ when there is something I feel the need to discuss. Is that not what a relationship is all about? Two people in a partnership who are able to communicate with just a glance? If only. Anyhow, talking to him was like pulling teeth or talking to a wall so after awhile I began to bottle up my feelings as well. Prior to that I tried sitting him down, writing it to him, being blunt, any possible way I could think of so he could just hear me. It seemed like it was no use.

Because of his lack of driver’s license, I had to drive us around constantly. I was always the designated driver, of course. Because of his unsteady work, I started having to pay more and more. I am usually a generous person and wouldn’t bat an eye at paying for things, but he rarely said thank you and I began to feel like I was being taken for granted. I was a mother, a taxi and then a bank machine on top of that. There came a point in time where he had to move out of his place, and into his Mother’s little one bedroom apartment in order to save some money for a damage deposit and whatnot. This was supposed to be a temporary living situation, two weeks to a month tops. He has been there for five months now. Living on her couch, because the company he works for (his Father’s company) was in the shits. Not once in this time span has he tried to look for a place, a new job, to better his life. He has expressed his discontentment with his life on several occasions, yet never did a thing to change it. Why didn’t he move in with me, you ask? For one thing, he is messy as messy can be. So! As soon as he moved into his Mom’s place, we started seeing each other less and less. I started working night shifts a few days a week, he didn’t feel like taking public transit out to see me, and I didn’t feel like hanging out in his Mom’s space all the time. This is when deeper problems arose. We fought constantly because I felt like we weren’t seen each other enough. I would send him a message or call him and he wouldn’t get back to me until the next day or a day and a half later. I felt chastised because I spoke up, and knew this was not normal. I found out he had been going to a pub regularly, made some new friends there. I found out because he pocket dialed me a couple times and heard him talking to some people in the background. I felt like something just wasn’t right, and one day while he was sleeping on the couch his phone went off and I picked it up and saw he had a message from a girl I never heard of. So…. I checked it. And she had invited him out to the pub to watch a playoff hockey game with her. When he woke up I confronted him about it and told him it was inappropriate that he was exchanging numbers with girls in bars. Of course he turned it around on me and just got angry because I looked at his message. The next weekend we were supposed to hang out but he said he was tired and was just going to have dinner and play some videogames. The day after, he ended up coming over and left his phone out again. So I checked it… again. Something in my gut was telling me something was wrong. He was acting strange (and I had an ex who cheated on me badly before). Sure enough, another girl had messaged him “Are you as hung over as I am today babe?”. Obviously I was enraged. Not only had I expressed how I felt about getting girl’s numbers, but he told me he was staying in the night before. So i gave him a chance to admit it. I asked what he ended up doing the night before. He stuck to his original story and said “not a whole lot, just had dinner and chilled.” Bullshit. I blew up and of course he had some bullshit story for me that was a complete fabrication. “Oh well, I was getting weed from my hookup and he doesn’t have a phone so I had to message this girl. And I had dinner at the pub, and she’s a regular there, so we had a pitcher and some shots.” RIGHT. So I broke up with him on the spot. But then panicked later on and we ended up getting back together.

From then on, we began to have trust issues. I gave him the benefit of the doubt until that point but that was it for me. Our relationship went consistently downhill after that and I became terribly unhappy. Our sex life dwindled down to nothing, as well. I expressed my unhappiness on several occasions, I tried to work on things but I started to realize it was a one sided effort. We drifted apart, seeing each other less. It was a battle to get him to even call or text back in the same day. So a few weeks prior to our break up, I am sorry to say that I gave up. I stopped trying. And it was only then that I noticed him perk up and start to call more often. But it was too late. I tried to accept him for who he is. I couldn’t so I tried to give him the loving push I thought he needed but I learned that you cannot change a person. And as much as I still loved and cared for him, I let him go. Apparently it was a major shock to him, in fact the term he used was ‘blindsided’. I don’t see how could not have seen it coming. So two weeks elapsed and at first he kept his distance. But I think it began to settle in that we were actually broken up about a week in. This is when he began to text and call. He begged for me back, professed his love for me along with many different apologies, finally acknowledged his wrongdoings and vowed to change. Now the question is, is that even possible? If he does change, would it make a difference for me? Could I be with him after everything we have been through? Or are we just far too different to be in a working relationship? The thought of it is so depressing. This is a person who I am still so fond of. I miss his companionship and reflect on the good times we had together and it makes me upset. He thinks I am throwing something good away, and that we can be happy. I just don’t have the heart to cut off contact completely, so I don’t know what to do. I love him to pieces but I think.. I hope there might be someone more compatible for me out there. And I worry if I would be settling if I took him back. I know people don’t change overnight. So am I actually willing to wait for him to deal with his self-proclaimed internal issues? So, Blockhead.. I apologize for this monster of a letter. I think once I started going my mind just started spitting out all these pent up thoughts. I am sure there is much more I could have included, and perhaps some of his is irrelevant. I just want to be happy. I want him to find happiness. And I don’t want this painful breakup to drag out any more. Although I have a feeling, it will..

Thank you for your time, I hope you will actually read this.

Wow that was obscenely long. I appreciate the question, but let’s keep these to under 10,000 words.
So much to cover here, lemme break it down into bullet points
1)He’s a piece of shit.
First things first. This is a fact. He’s not a bad person, but he’s extremely typical of how dudes get. I think that the way he was in the beginning of the relationship (mr. awesome) blindsided you into thinking the way he was acting later was a phase. but, sadly, this is how he actually is. At least as a boyfriend. I’m sure he’s a good guy or whatever but once a boyfriend stops giving a shit about being a boyfriend, it’s never good for the girl.

2)He’s probably depressed
I’m not shrink but all things point to him being pretty fucking depressed. I don’t blame him. He lives on his moms couch, smokes weed all day, barely works and has (had) a girlfriend he obviously is in no condition to maintain, try to talk to him about shit he doesn’t even wanna think about.
I’d say his trips to the bar are the only thing keeping him sane. It’s probably the only place he goes where he feels like he has any worth at all.

3)You are a doormat
It’s not your fault. You’ve be betrayed before. It’s par for the course. You’re a caring person who’s giving this dude enough chances. you’re holding on to a memory of a person you once knew every time you envision him in your life. But , if he gets back in, he will restart the cycle and walk all over you. Like I mentioned before, he’s in no position to have a girl friend right now. His life is way too fucked up. It’s sounds like he’s a cast member of “Winter’s bone”. AT BEST, he should be fucking bummy skanks at the local watering hole. That’s the pinnacle for this guy, until he gets back on his feet (if he ever does). Basically, his downward spiral is not you problem.

4)Phone checking never ends well
Phone checking is ill cause , if you’re checking it , you straight up don’t trust the dude. And chances are, if you don’t trust him, there’s a reason for that. Sure, you got cheated on before so you’re sensors are sensitive but the real reason you checked is cause you were suspicious of this guy.
On the other hand, you’re invading his private territory. As guilty as he is, you’re out of line as well. THis may be drastic but if you’re in a relationship when hacking into facebooks/emails or reading old texts is a thing, then you should just break up. Already, the trust is fucked up. Sure, there are some people who do that shit right away (and those people deserve to die alone with 9 cats in a one bedroom apartment) but for normal people in healthy relationships, you just don’t do that. i understand how trust issues and overall insecurity play into this but recognize, if he was the right guy, you’d be past all that by now.

5)DO NOT get back with him
You know this. Even after the book you wrote me I can tell it was just you wanting someone else to tell you what you already know. Not only is he not changing, he’s probably gonna get worse. It’s not like he’s gonna wake up one day and just decide to be this awesome boyfriend, get an apartment ,a new job and life will be perfect. That takes time and most likely won’t really ever happen anyway.
So, cut it off. He’s only coming back to you cause he’s a fucking loser with nothing else going on in his life. You’re literally just there to be a sponge for his sorrows, neediness and sperm. Don’t be that sponge.

hey, i’d love your advice/opinion about a situation i’m going through right now.
i dated this guy for a whole year (09 -10) and we did a distance thing the whole time between two different cities, but he ended up moving to go to Uni a couple of states away in Fall ’10 (after giving me a nice ol’ diamond) and he had a meltdown and said he couldn’t do distance at the moment. i give the guy space and we this summer rolls around and we were inseparable, but we established that we were just going to enjoy the summer w/o worrying about anything.
the bro talks about a future with me all the time: wedding shit, living together shit, having kids and pets shit; but the problem is, he won’t ask me out again/won’t commit because he says he wants to focus on his studies and doesn’t want to get involved with anyone. he says the time isn’t right right now.

i know that you’re usually supposed to take bro talk at face value, but what the fuck do you think is going on, Uncle Tony? 😦

Hmm…either he’s an evil dude or he actually means what he says.
Let’s look at the two sides,
He’s Evil:
If he’s evil then he’s just doing this to keep you around for his own amusement. He fills your head with talks of weddings and and babies as a mean to keep you locked in. But , when he goes back to school, he’s fucking everything that moves and not even thinking about you. he’s a sociopath with no remorse who may very likely one day try to talk you into a threesome.


He’s just being realistic

Long distance relationship are a mess. He might have every intention of being with you down the line (a few years) but trying to maintain a relationship that way is not only annoying, but tiresome. It’s wears thin on what might have otherwise been a perfect match. So, perhaps, he’s thinking that it’s better to just see what happens. He could have every intention of being with you eventually.
The real question is, are you willing to wait? This will mean you will be holding him in your back pocket for the time being. Every dude you meet, he will be looming over you , stopping you from moving forward like you might if you were totally free of him. It’s basically vaginal handcuffs. So, if you feel that deeply about him, believe he’s earnest and are willing to wait, then do it. If you have doubts , then don’t waste your time.
I’m a middle of the road kinda guy so I’d say just see what happens. It could work out great. You never know. But if the weight of the situation is too much, you can always hit the eject button. Even then, it could still happen down the line.

6 thoughts on “Ask Dr. Tony Volume 5

  1. Good work, but I could have answered these questions in fewer words.

    1) Unless you’re a politician, go for it.

    2) The problem with your ex-boyfriend is that he is a male, and you are clearly a lesbian. Run with that.

    3) Your fiancee has another girl at University.

    – Dr. Reggie

  2. You kind of answered this question this week already but I’ll give it a shot;

    So I’m kinda dating this guy, it’s uncanny how similar we are and how well we get along. I don’t think I’ve ever met someone who is as perfect for me as he is. I’m pretty sure he’s clinically depressed (or whatever happens to some single men after they hit 30).. He seems very jaded and is pretty pessimistic. I don’t really care ’cause I think brooding middle aged men are kind of hot in a way. I’m also pretty sure he likes me the same way that I do him, but I think he might be afraid because all of his relationships were pretty shitty and women have fucked him over really badly. So, I like him, he likes me.. Why aren’t we together? Well, he has a few other girls that he still fucks/dates and can’t get rid of because they’re emotionally attached (or so he says, and I’m paraphrasing hugely here) I’m not a jealous girl/don’t really care that he’s fucking other people ’cause we’re not together, I understand that people have baggage and what have you and maybe if I give him more time, it’ll happen eventually. He also says he’s not ready to be in a relationship (this is where I think him being depressed comes in) even though he can commit to one girl, despite the fact he says he wants a girlfriend. However, he wants me to stop seeing other people. He says it’s for safety reasons, but I know it’s because he wants to have his cake and eat it too. With what you said about having him in my back pocket, I know that I’m attached and if I date any other guys, I will always be thinking of him and I wouldn’t want to lead anyone on or anything like that because it’s just unfair. So, I’ve decided to be monogamous because of that (and because I don’t want to be with anyone else) So my question is, am I being stupid? Am I setting myself up? Could it be that he’s evil and keeping me around for his amusement and sexual satisfaction? Or is he just depressed and doesn’t know what he wants?

  3. Thank you for your thoughtful advice. I’m sorry it was such a novel. You were right about everything. There were even things I found out after the fact that solidified my decision further. So thank you very much for reading and responding.


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