Ask Dr. Tony vol. 51

Hello all,
Welcome to another edition of “Ask Dr. Tony”. An advice column for people who, for some reason, want to ask a niche hip hop producer what to do with their lives. Thanks to all the people who recently sent in questions. I can always use more. If you have a problem in life or love and want an outsiders opinion, fire away. It’s always anonymous. Send questions to or leave them in the comment section below. The Dr. is always in.
Let’s check this weeks batch…

Dr. Tony,

Help, I want to have sex with my roommate. I know it would be a terrible idea but he’s my ideal man. A blonde haired, blue eyed dream boat I can totally imagine setting up house and buying a mini van with. My friend suggested I just crawl into his bed one night and start S-ing his D. But I dunno i think that might make things awkward. What should I do??

Well, this could go a few ways (if you decide to take it there).
1)He’s into it and now you live with your brand new boyfriend. Good on paper, bad in reality. Not saying it can’t work but there should a grace period of dating where you both don’t need to shit near each other all day long.
2)He’s not into it, you get shot down and now you live your life avoiding him at all costs.
3)He’s kinda into it but not like you are. He will have sex with you but he’s also not looking for anything more than casual…which could be fine for a while but will undoubtedly get messy when he starts bringing other girls around (assuming you continue to like him)
4)You hook up once. it’s wack. You no longer feel that way about him. It’s awkward for a little bit but you can blame drunkness (or whatever) and eventually things go back to normal and, most likely, you’re better friends for it.

So, as you see, only one of those has an outcome that isn’t awful. Obviously, my advice is to not shit where you eat. And don’t fuck where you eat either. This may just be one of those situations where you gotta just sit on your hands and chalk it up to bad timing. Also, masturbate furiously to him. That could work for or against you though.


This is a simpler question than it seems, but I’d like to give some context. At my workplace (retail), my fellow managers and I hired a young man, age 22, who seems competent enough to do his job and remain employed, but so lacking in certain areas mentally and socially that it has become creepy to work with him.

The first red flag is that he’s a kiss-ass to us, and a real arrogant little brat to all the women. Complaints about his tone-deaf personality have been relayed to us, but he hasn’t done anything severe enough to warrant a firing/writing up. He pushily demands the women to train him at tasks that he has not been asked to do, nor is he even expected to do.

On his resume, he listed his previous job as a “shipping manager” at a retail store. I have a friend of a friend at said retail store, who confirmed that this new hire dude definitely was not and never was a shipping manager. I should’ve noticed that a 21 year old shipping manager for a major chain store sounds ludicrous, but I didn’t make the final decision on hiring. My boss is a real nice guy who gives new hires the benefit of the doubt.

One night, I drove him home because he needed a ride and does not have a driver’s license. He told me I’m easy to talk to, and out of friendliness I humored him while he started getting personal, saying things like, “how do I talk to women?” and “I’ve never dated” and “I don’t like music.” I responded, “no music? Like, nothing? Not even Beethoven? You’ve never heard a piece of music and felt emotional or moved, or amused, or anything?” He shook his head. This guy does not like music at all! I asked him what he’s passionate about and he said “videogames” and remained cagey about what he does in relation to videogames.

While at work, he stares at his phone until I tell him to do things. He added a female coworker, on the job, on facebook, while in the same building, and messaged her. Now, I did not give him specific advice on how to talk to women, like, “hey bro, add the girl on fb while in the same room! It totally works!” I gave him the most harmless tidbits I could, like, “just listen to people and treat them with respect and humility, things will proceed easily from there.” He doesn’t seem to pick up on behavioral subtleties. He asks weirdly rude questions like, “when will my schedule be ready? How am I supposed to know when I work when the schedule isn’t ready yet?” On a stormy day, this dude even asked me, “is it raining?”

My thoughts are that this young man is mentally underdeveloped, but also seems to be an arrogant, manipulative little liar, and not a very good one. I should be able to get him fired based on the fact that his application seems to be a bunch of lies. He keeps referring to his “roommate,” but at other times has admitted that he still lives with his parents. The other, more paranoid part of me has thought that this young man is potentially dangerous or unhinged, although the jury is still out on to what extent. Obviously I don’t want to tip things over into chaos, but there needs to be a sensible, reasonable way of putting an end to this. Any advice is greatly appreciated, and sorry this is a long explanation.

Clearly this dude has issues. Like, up and down the board. He’s socially inept and definitely mentally disabled in some form or another. Sounds like he may have aspergers or , at the very least, is on the spectrum. Problem with me giving advice here is that I’m not familiar with what’s okay and not okay when it comes to firing people. The last time I worked a regular job, you could fire someone for whatever you felt like. Granted, I worked at a bakery but still…There wasn’t as much space for uproar and suing as there most likely is today. Especially in a bigger corporation.That said, you seem to know the easy out. If he lied on his resume, there ya go. Also, making female co workers uncomfortable , being on his phone all day and even the paranoid “he might be a psycho” feelings he gives off…I’d imagine those are all grounds to let someone go. That last one especially with all the shootings that have been happening.
All that said, he could just be incredibly socially awkward. Which is harmless but also, not your problem. Let him be someone else’s issue to deal with.

I have a friend who’s married to a girl from south america who moved to america to be with him (met through high school foreign exchange). if things don’t work out, she would want to leave america and return to her family. he has admitted to her that he has feelings for another girl — who he spends lots of time with — but that he would never cheat on his wife. recently, while talking clumsily about some philosophical concept he posed the question “if a man cheats on his wife, is it wrong if it brings him and his mistress more happiness than it brings his wife sadness?”

who do i ask what questions of/tell what things to? all three people involved are fairly recent (four months) friends of mine, but we’ve been spending ~3 days a week together and i work with the wife most days of the week.

The wording of that last paragraph is confusing as fuck but I think I get the overall questions.
Who do you talk to about this? Umm…no one. Mind your fucking business. You’re saying you have known these people for 4 months and you’re trying to fix a marriage you have absolutely no involvement in? This is their problem. But more than that, it would be nosey of you to interfere in any way. I understand that you may not like what going on but these are all adults making their own choices. No one asked you to referee their lives.
Also, I’d be willing to bet the dude is already cheating. That kind of tension can only go so long before it boils ever. Within 6 months, this whole thing will probably be resolved. South American girl will be back in South america. The guy may or may not be with the side chick, and you will have had nothing to do with it. At least i hope. I get that people sometimes have an urge to try and fix everything that’s broken around them but , a lot of the time, they just end up making it worse.

Dr. Tony:

You mentioned that in college you missed lots of sexual opportunities. I recognize myself has being in a similar position (as in: why did we just sit on her bed and giggle for forty five minutes while making extended eye contact? oh wait sex). how does one break out of this obvious young-man’s pattern?

For me, I broke out of it when I stopped giving as much of a fuck. When I was young, every moment like that was tense and anxious. The fear overrode the excitement. Those feelings still exist but, as you get older, you learn to trust the signals being thrown at you. I’ll never be the type of guy who makes bold power moves at girls. I’m just not that guy. I’d imagine you’re the same way. However, once you get more comfortable in your own skin, gain a little confidence in yourself, you just kinda go with the flow. You learn to close in your own way. Some dudes go in for the kiss at first sign, others just kinda let it come to them and act accordingly.
It should also be noted that girls also get more aggressive with age as well. So, that same girl who you would lay around in bed with for 2 hours almost kissing while you agonized over if her leg was touching your on purpose, will straight up just attack you 5 years later.
The bottom line is that you gotta not look at every situation as a life or death kinda thing. Also, step back from your situation and look at it from the outside. Like , you go home with a girl after a night out. You’re in a bed with her and it’s after a certain hour. By no means should you expect sex but, at the same time, I think it’s safe to assume she may be down to make out. If she rejects you? Then deal with it like a gentleman. But know that, 95% of the time (assuming she’s not resisting along the way) she probably likes you. Just to clarify, I’m not talking about shy girls who get pushed into shady situations but aggressive dudes. That’s totally different. This is more when a girl is leading the evening and , there you are…in bed with her at 2 am. Chances are, you’re good to go. Trust your instincts. A simple thing you can do is just bring up making out conversationally. Talk about it. Her reaction will guide you.

2 thoughts on “Ask Dr. Tony vol. 51

  1. I’ll second exactly what Tony says to the last question. Women completely change when they hit 30. They are completely aggressive. And the best part is that these women now know exactly what they want and how to get it/do it sexually. You’re in for a treat, my man.

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