Ask Dr. Tony Vol. 29

Hello everyone. It’s time once again for me to dole out some of that good old advice about life and love. I’m not a doctor and I dropped out of school my freshman year of college but I sure as hell give better advice than your stupid homeboy/girl who’s trying to salvage your frail ego.
So, if you feel the need for some help from a third party with no stake in anything other than being honest, holler at your boy. Email me questions at:
or leave them in the comment section below. There are always anonymous so it’s a safe place to totally reveal you most deepest and darkest secrets to the internet.
Alrighty, lets get into it…

Hey Tony,

So you seem very wise and mature in the dating realm, and thus I am reaching out to you with my boy problems. I started dating this guy a little over a month ago, and things seemed to be going really well. We decided since we were both going to be traveling the next few months that we wouldn’t be exclusive. I was cool with this, and things continued to go pretty smoothly. He went out of town and we texted a lot. When he came back we ended up having sex, and things seemed fine afterwards. He texted me the next day, and the day after that I asked him if he’d want to hang out. He said he had plans but he’d let me know. I didn’t hear from him between the next few days before my flight, even though he knew I was leaving for six weeks. The night before I left I texted him seeing what was up. Later on in our conversation he apologized for not having seen me before I left, and I said that I wished he would’ve said something earlier since it had kind of confused me. He apologized and said he wasn’t trying to mindfuck me and the conversation kinda ended with me just saying things were fine. The next morning he texted me again saying he didn’t feel good about the way we left things and asked me if I could talk. We weren’t able to meet up so we just ended up texting. He said he didn’t want me to think he had bad intentions and that he wanted to stay in touch while I was gone and that he hoped I wasn’t too upset. I basically responded saying that everything was okay, I just wasn’t sure where we stood after we had sex, since he had kind of lost touch and didn’t try to see me before I left. Basically, we left things on good terms, but I haven’t heard from him in a couple of days now. My questions, are then, I guess, what is your interpretation on this whole situation Block? Am I blowing things out of proportion? Was I expecting too much after a month of dating? Is he an asshole? Busy? A busy asshole?

He sounds to me like he doesn’t really know what to do with himself. There’s something about a non-commital relationship that can be confusing to a man. Cause, in a way, you’re giving him a free pass. He gets to be both single and have you at the same time. So, basically, he’s single. I’m not saying he was out fucking a different girl every night or even fucking any other girls but that freedom he was allowed can turn something that might be a little more black and white into a grey area.
Now, he certainly just could have been busy the entire time but I’m of the school of thought that, if you wanna see someone, you can always make time. Unless he’s working 90 hour work weeks and lives far away, it should never be impossible to connect with someone you want to see. Hell, I’ve seen people who work those kind of hours still make time for people.
So, this leads me to believe the guy you were/are dealing with simply is/was unsure of the whole thing. Possibly cause he knew there was a cap on it, with you leaving. It’s possible he really did/does like you but didn’t want to get too involved cause he knew you were not sticking around. personally, when i was ever in a situation like that, I’d liken to it as a godsend cause it was like you could just have all the good parts of a relationship then the person would go away before shit got annoying. Granted, I was an asshole when I was single. Still, this guy pulling back as opposed to not just having as much sex as possible with you before you leave actually leads me to think he’s not an asshole. He’s probably more sensitive and aware of his feelings. Or he was fucking tons of other girls. I suppose we’ll never know, will we?

What are you thoughts on texting vs. calling girls? I’ve had a few instances recently when girls have taken hours or days to respond to a text and there end up being a lot of mixed signals. Isn’t texting kind of a step back technologically? I find a lot of the confusion that arises during a text conversation could be cleared up by a quick phone call. Should young people try picking up the damn phone for once instead of using it like a telegram?

Texting is a gift and a curse.
On the bright side, it’s revolutionized flirting and how people interact in general. I often lament about how I wish texting was a thing when I was in high school cause I’m way better at typing than I am at speaking which would have led to an exponential growth in my teenaged sex life.
However, for the reasons you mentioned and more , texting is probably the worst thing to happen to human interaction in our lifetime. It’s gotten to the point where people are appalled when they get a phone call. I’ve got friends who ONLY respond to texts. I get it though. I HATE talking on the phone. There are like 4 people I enjoy talking to on the phone and they all live in other cities. But , sometimes, people just have to suck it up and make a phone call. There are some situations that can’t be conveyed properly with the short handed written word. I can’t tell you the amount of times relationships have been hurt by people misunderstanding texts or people who text in a certain way tactlessly infuriating people without even knowing it. The problem with texting all the time , when dealing with the opposite sex, is that not everyone is good with words. Some people are downright retarded. Whether it be that they can’t convey a clear thought or they just have a particular tone to how they write that confuses people…some people just need to stop all that and pick up a fucking phone so they can eliminate any confusion. Especially if you’re having a serious talk. No one should break up over texts. Booty call terminations maybe…but nothing deeper than that.
Sadly, I fear this is only gonna get worse and I foresee a time in the future where people will cease talking altogether. We will just sit around dinner tables instant messaging the other people at the table. Eye contact will only be made right before they share a first kiss but will soon be followed two people having sex while sexting and sending each other text photos of the very sex they are having at that moment. A world destroying astroid can’t come soon enough.

My gf and I have been dating for two years, there was a period that I went off the deep end with the booze and drugs and lost a considerable amount of her trust. She started second guessing anything I did with other friends (male and female especially) or where and how I would spend my free time. We’ve managed to patch up most of the issues we had since I got sober (go figure) about 6 months ago. Now we joke, at times, about how paranoid she was and some of the sketchy shit I did to get her to that point. She was recently contacted by her ex-boyfriend (“The asshole with a small penis” she calls him) and decided to go out with him to catch up over drinks.When she told me I said “Okaaay? Well have fun but If he’s such an asshole,why spend more time with him?” I’m not really the jealous/insecure type but I find it rather odd that she would do this. Maybe it’s just foreign to me because I’ve never maintained a relationship after a breakup aside from the occasional hate sex booty call.She said that they got along fine as friends and she just wants to see how he’s been.She’s very faithful and is completely trustworthy but I could use an outsider’s opinion on what her motivation might be.

I don’t think it’s a big deal. I have ex-girlfriends I’m still cool with who i would have a meal with devoid of any foul intentions. Granted, I wouldn’t be super psyched to do it but it also wouldn’t be the end of the world. I think part of people doing these sorts of things is a basic curiosity we have about the people in our past. Sure, some people will do these kinda things with a faint flicker in the back of their minds that , maybe, there’s some thing still there. But I’d guess that, in general, it’s just like two old friends meeting up.
I do find it odd that she would even want to see this guy she openly dissed to you but, then again, her calling her ex “the little dick asshole” might just be something she did just to make you feel more secure about her past relationships. For all you know, he was the love of her life and his dick looked like a baguette. I mean, she dated him and is willing to see him again, how big an asshole could he have been?
regardless, I wouldn’t worry too much about it. Just keep an eye on her that night and if she starts acting distant or weird the following days after that, then get suspicious. Also, if she comes home complaining about him in a petty way…like a girl who was perhaps dissed or is butt hurt, that’s a tiny red flag that he might still have some sort of grip on her. I say this cause, if she was truly over it, she probably wouldn’t give a shit.

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.

Hey dude, guess what? IT NEVER GOES AWAY. I don’t think there is a man alive who thinks “Well, I’m totally satisfied with my sex life prior to my wife!”. As men, our lives are shrouded in regret about sex we should have had. That goes from the guy who only slept with his wife (AKA YOU) to Hugh Hefner. It’s simply an unavoidable fact. I had a fun time as single person. I look back on it fondly but I’d be lying if I said I didn’t wish I had been even more active than I was. While that thought might make my girlfriend want to vomit blood it’s simply how we, as men, are wired. Hell, I’m sure girls feel the same way. Just not as grossly as men. A dude will sit around pondering the night he opted to not fuck some low life girl he met at a bar who probably had hepatitis Z with great regret simply cause we feel we may have missed out on an experience. It’s just how we are as hunters and gatherers. That doesn’t only apply to food and life necessities. It applies to memories and ego fuel.
So, yeah man, it’s not just you. It’s everyone. Rest easy that, even if you had fucked tons of girls as a single guy, you’d still be ogling that girl that works at starbucks like a creep and wondering what her underwear looks like. It’s human nature AND regrets. They go hand in hand.

4 thoughts on “Ask Dr. Tony Vol. 29

  1. “It’s just how we are as hunters and gatherers. That doesn’t only apply to food and life necessities. It applies to memories and ego fuel.” fucking on point!

  2. I love how you led to “a world destroying asteroid can’t come soon enough”. “..his dick looked like a baguette” was another highlight. You always make me laugh. We have very similar senses of humor & writing styles. More times than not, I’ll write a very long winded response to one of your pieces & while I’m proof reading it for grammatical errors & moments of utter stupidity, I simply erase it or don’t hit send. I’m becoming a reclusive old codger & I’m turning 39 in 2 weeks. Not a good sign. I need to move back to a reasonably sized city before I completely lose it. I’m currently growing a silly mustache for my own amusement during the fleeting moments that I look in my bathroom mirror. I’m on disability with a severely fucked up spine, so I have a lot of time on my hands. I’m a good enough dj to make a living at it, but I’m getting to an age where I’m not sure if I want to do that anymore. Who am I kidding? I better go ahead & do it while I still look a lot younger than I am & don’t walk with a cane or use a wheel chair.

  3. 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!

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