Ask Dr. Tony Vol. 31

It’s been a while but the doctor is back in. Honestly, I was just waiting on some more questions and you guys delivered. Here’s the thing, I need you to keep delivering. If you have anything you feel you need advice about (love life or life in general), send me those questions. Email them to me at: or leave them in the comments below. Everything this is anonymous so don’t be a pussy about it.
Anyway, in case you’re new to this, this is a column where I answer questions submitted by readers about their fucked up lives. What qualifies me to do this? Absolutely nothing. Aside from being told by friends that I’m a level headed, honest guy who gives solid advice , I really have no business telling you strangers what to do with your lives. So, you know, keep that in mind. I’m not a doctor. I’m not even a college graduate. But, I will shoot straight and , best of all, I don’t know you so it’s not like I’m biased. Trust me, your friends are blowing smoke up your ass.
Here’s this weeks batch full of lost loves, cheating and a lady who has lots of love to give to her friends. God bless her heart.

Dr. Tony:

I’m looking for a little guidance here. I recently went to Austin, TX to hangout with a 40 something I know under the premise that it was a date sort of thing that weekend. I’m 29, and if I’m being honest, hooking up with her over this weekend definitely checked an item off my bucket list; that being bagging a cougar. We have hung out before; I stopped in to visit her on my way back from a vacation to Padre in south Texas. I live in OK, so it’s not a far drive, about 5 hrs. She’s trying to catch feelings, and while she’s a cool lady and we get along great, and she is definitely attractive, I dunno if this is an avenue I want to go down for a few reasons: 1) She lives in Austin and I’m pretty sure has no plans to move 2) Austin is the shit but I’m well into a successful career in OK and have a bitchin set of friends and I don’t want to have to try and rebuild either of those things in a new place and 3) I dunno if I want offspring yet, I feel I might though, and kids are definitely not in this gals future anymore. All that being said, should I entertain a semi-long distance relationship with this lady to pass the time for now, or figure out a way to remain platonic friends?

I love that dudes have sexual check lists. I mean, I get why it’s just a funny thing to obsess over. They treat is eating or something.
“I gotta eat KC BBQ before I die bro…and also I gotta bang a paraplegic on a sex swing!”
Anyway, considering this seems like something you did to add another notch on your belt of sexual majesty, I dunno if entertaining a long distance relationship with this woman is the right choice. For one, it’s a long distance relationship and those kind of things should only be relegated to people who genuinely feel they have to be together. From reading your words it’s clear she’s not that important to you. Calling a girl you’re fucking ” a cool chick” is generally male code for “She’s alright and not super annoying but I’m not trying to wife her up”.
Secondly, if you’re aware of her starting to catch feelings and know that you’ll never feel the same way, then you’re just toying with her emotions. Sure, she’s 40 and has probably been through the ringer already enough to know what’s really going on but still…if just seems like you’d be keeping her around as someone you can have sex with anytime you feel up for a 5 hour drive.
So, I’d say let it go and chalk it up to the distance being impractical for what you two are looking for in the relationship. OR be a total lying piece of shit and just tell her what she wants to hear, keep fucking her and live your life in OK like she doesn’t exist. You could always do that too…really depends on how big of an asshole you are.

Dr. T,

I have hooked up friends in the past. Maybe because it was either like a drunken fluke…and/or as single attractive adults it only seemed natural for it to happen eventually. Obviously we have enough in common that I like them as people enough to have hooked up with. Thing is…we also have mutual friends in common. For the most part…with a couple of them, we are still good friends and its not awkward at all. Probably because we’ve drawn the line and not hooked up a second time.

One “friend” yeahh i admittedly was more naive to his sweet talk, leading on, and to what his closer pals say is his notorious “man-whore”ness. I am not salty, I was just definitely caught up on feelings that were hard to forget until finding someone else who I shared that kinda chemistry with. Thing is… that last someone was an old friend of his, someone who I have hung out with much more in the past year by either going out to shows alone or socially. We have a lot in common musically, laugh at each other jokes, and have flirted a lot in the past.

Since we have a fairly close group of friends… It just feels like we are walking on thin ice whether to continue hooking up because it could ruin a perfectly good friendship dynamic. Should I say something, if I’m just slightly crushing and want to pursue things further? Or continue to play cool?

In short, What’s the deal with hooking up with friends? Is there such thing as friends with benefits, possibly even more, if we already hang out so often?

First off, you sound like you have a problem of shitting where you eat. Nothing wrong with casually and drunkenly hooking up with people in your circle but, from the sounds of it, you might be 5 or 6 dudes deep in a crew…and that’s not a good look. I don’t mean that in a “Slut shaming” kinda way either. If you like hooking up and it makes you happy, do you. However, there is a good chance the boys of your friend circle are keenly aware of your practices and reacting accordingly. I’m just saying, be aware of who your friends are and who are just dudes that are nice to you cause they’re trying to get in your pants. You’d be amazed how many male “friends” would vanish if you suddenly grew a penis.
As far as friend hook ups, I’m 100% in support of them as long as both parties involved are on the same wave length. The second one person starts to feel more than the other, it’s a disaster waiting to happen. So, really, Friends with benefits can work but it’s kinda like baking a cake. You need the exact ingredients and measurements. Too much baking soda and that cake will taste like shit.
Beyond that, it is rare that a friends with benefits situations turns into love. Life isn’t that Justin Timberlake movie. I’m not saying it’s impossible, just highly unlikely. To let you in to the male psyche, many of us tend to know our long term plans for a girl very early on. We know how far we’re willing to let this thing go before it’s past the point of us being into it. Meaning, we’ll meet a girl , think she’s cute but know right away, for some reason or another, that we’d never settle down with her long term. Perhaps she’s a girl we’d like to have a booty call relationship with or maybe just date casually but that’s it. As you can imagine, this kinda shit leads to girls being confused constantly by our mixed messages and when we randomly just stop calling/texting.
So , with this in mind, think about what you want out of the men in your friend circle before getting involved with them. If you just wanna get laid and you’re not bothered by the social stigmas of that, then it’s generally all good. If you want to date a specific guy and actually like him, you can’t treat it like you would the other guys you’ve hooked up with in the crew. Basically, these type of relationships are gonna be what you make them. Just be aware.

Ehi Dr. Tony, I have a question for you. Here’s the situation: Me and my girlfriend are together since one year and a half, I really love her but this summer I met my ex girlfriend that I didn’t talk with since three years; I met her in a party. Then we started talking about this three years that we didn’t talk and seen each other, I told her how she made me feel when she left me. From that day we got back in touch with each other, we start texting and we discovered that there was kind of attraction beetween us. One week later we went out for a beer and when I brought her home we kissed each other. I’m still with my girlfriend, I love her but she doesn’t know what happened; sometimes my ex grilfriend and that kiss come to my mind. What would you do? Would you continue to be with you girlfriend or you put all into play with the other girl? Sorry for the english but I am italian 🙂

Well, even though it’s minor, the cheating seal has been broken and the wheels are obviously turning. I have a feeling no matter what I say here your mind is made up. The flicker of desire one has for an old flame can grow quickly and , the fact she’s on your mind that much, leads me to believe it’s only a matter of time before you’re obsessing over her and your new girl catches wind.
Personally, I would generally advise against rekindling old loves cause , sometimes, we tend to forget why they ended in the first place. It seems as if only the good parts of this person come back, meanwhile, we forget all those moments where they’d walk out the room and you’d be sitting there giving her the finger behind her back. And if this girl was one who didn’t speak with you for three years, I gotta think it ended in a somewhat turbulent manner.
Regardless of either, you already crossed the line by making out, as harmless as it may have been. The whole thing would lead me to believe you don’t really wanna be with your current girl that much (cause if you did, you woulda been able to control yourself). Maybe you need to just be single and not deal with either of them?

If someone is in a monogamous relationship (not married) and you completely have feelings for that person, should you let them know or completely hide it? Like, how horrible is it to kinda pursue someone with a girlfriend even though you know it probably won’t mean shit? I don’t mean this is a creepy or forceful way, but sometimes I get this vibe that this boy with a girlfriend (who doesn’t make him very happy) wants me back. It’s not like I’m gonna start caressing his dick, or even kiss him…but I’d date him in a heartbeat if I had the chance. What kinda boundaries do you think there are in situations like that? All is fair in love and war? I guess I kinda see it as like you gotta keep a baseline level of respect but if he wants to stray from his girl, that’s his call.

So, umm…tell me more about this dick caressing, penthouse forum.
Listen, if a dude is taken,he’s taken. You can flirt and make him aware that, if he were single, you’d be a willing option, but beyond that, you’d be an asshole to interfere in anyone’s relationship for your own selfish desires. And all the “she doesn’t make him happy” shit is a bad excuse. Even if she doesn’t, it’s not your job to fill that role.
Even if the dude flirts back, it doesn’t mean much. If he’s a wifed up dude, he’s probably just happy to know he can still attract women at all.
And , let’s say you do flirt and the guy escalates it to where things might get physical, you realize you’d be willfully dating a dude that has no qualms with cheating on his girlfriend? I know you could argue about how you’re a different girl than her and blah blah blah but , really, cheaters gonna cheat.
From the sound of it, you’re 100% down with being a girl he cheats with as long as you don’t instigate the actual first move. That’s cool and all and , if you don’t believe in Karma, then what’s stopping you? Just know that by doing so, both you and the dudes are starting something from a bad place. It’s rare something like that will grow into anything that isn’t eventually toxic for both parties involved. Not saying it’s impossible, just highly unlikely (that should be the tag phrase for this column). And, really, don’t be the “other woman”. For the sake of honest and trustworthy women everywhere. That’s just corny. It just gives us dudes yet another reason to be assholes to you guys and justify our shitty behavior.

9 thoughts on “Ask Dr. Tony Vol. 31

  1. Skeezoids. Nothin but skeezoids. Is that what we’ve come to nowadays? Advice for not being a slut? You’re fighting the good fight Block. Tell these bitches to keep it in their pants.

  2. Re first question. Girls have sexual checklists too! At least some of my friends and I used to and we were obsessed with checking countries off for our figurative (p)ASSports, meaning that every nationality you hooked up with got a “stamp.” Perhaps what was different from a guy’s list is that hooking up could be anything from making out to fucking for it to count.

    Actually the whole thing sounds whorish now that I think about it but what are you gonna do. Ps: I love that this is anonymous, yay!

  3. To the chick at the end, I agree with you Block that you shouldn’t willingly interfere with a relationship….but a side of me is like you can be his friend and flirt a little and then make a jump for it if he does leave the girl. I feel like that sometimes happens, so if you like this dude and he truly is “unhappy” then just wait for him to dump the other girl then go in for the kill.

  4. Ugh ladies! I feel like it took me a looooong time and many confusing hook-ups to get to this mindset, but the power dynamic that is sad to me is one that still places so much emphasis on attaining some man’s affection as the goal for happiness. No doubt I want to be loved and all that fuzzy stuff as much as anyone else, but it’s not nearly as important as being proud of my own accomplishments or feeling like I stuck to my beliefs. I have definitely used men that I was sleeping with and the romantic feelings I built from our time together to distract me from real problems and even boredom in my life. But that is not real love, and it’s not mutual, even if it seems that way in your head. It’s a device for escapism, and ultimately it won’t make you as happy as figuring out what it really is that will make you feel accomplished. Plus, how are we going to wonder why we are getting taken for granted when we set it up for ourselves that way? Now, I do tend to rock a couple steadies and am definitely no saint, but you’ve got to make sure you yourself are completely honest with what the terms these things are on and that it is benefiting you more than causing you stress by distracting you in your me-time. OFF THE SOAPBOX!

    • So true stranger, all of it! Wish I had heard that during my buds with benefits stage, especially the device for escapism part.

      But what does “rock a couple steadies” mean? I have heard this before and don’t know what it means and I don’t care if I sound CLUELESS by asking

  5. Dr. Tony, will try to make this as short as possible
    3 months ago i met this guy through a good friend, we all went out for drinks and i remember being immediately attracted to him, a little through the night he began to flirt with me and eventually we made out in the club and couldn’t get our hands off each other,we really bonded through deep drunken conversations and confessions, it felt like weve been friends for a long time and i dont think ive ever felt that comfortable with someone that i just met. (because i had just gotten out of a dreadful relationship i really wasn’t looking for anything beyond a little fun and sex.) therefore i decided to go with the flow and sleep with him that night. i ended up spending the whole night and next day with him, it was great. he also told me that hes never felt that comfortable with someone new, no awkwardness or anything. so that next day ended when i had to travel back to my country. we exchanged numbers and i went to the airport thinking last night was great but it will clearly not go anywhere as we live in different countries.
    I text him a day later telling him that i had a great time etc. and since then we started texting and calling eachother daily, we got to know more about eachother yet, how much can you know when the person is not in your face?!
    About 3 weeks after daily texting, calling and phone sex, i was traveling again for a month to a country thats near his country, so he came to see me the first weekend, and we spent 3 days together. it turned out to be even better than the first time we met. I still didn’t have my hopes up for anything to escalate and i wasn’t thinking of it too much i was just busy being carried away with the moment. Also most importantly, that weekend he referred to me as his girlfriend. Another 2 weeks pass and he comes to see me again for one night, every time we see eachother it just seems to be getting better n better. that last night he told me that hes developing really strong feelings for me and i def was on the same page as he is. everything was going just fine, up until a week after the last time i saw him he suddenly started acting a little distant, less phone calls, no texts, which is always a bad sign, plus i know that long distance never works out so i also had that in mind. he told me that he was very stressed from work and i understood that, i never gave him a hard time about it as i really believe in giving ppl their space. for a good week he would suddenly act distant then suddenly be all caring and nice, and i just went along with it like theres nothing, at that time he told me that he will be going for masters in summer which means he will be in a completely different continent and time zone.
    His family member gets a serious health issue, which brings him to be more distant for yet another and final week. i tried to be there for him yet in the same time i didnt want to impose too much.
    to cut this very long story short, he calls me end of that week and tells me that he wants to put what we have on hold (which i understood as a break up) as he has alot going on right now and he cant handle having any obligations. I was very understanding and accepting of what he was saying, i also believed it was for the best as i still think long distance ruins everything. at the end of the break up phone call he told me that hes falling for me. ironic.
    3 days after the break up he calls me briefly to check up on me and thats the last ive heard from him.
    ive been around enough to doubt things around me, so my question is, did this guy play me just to get what he wants or does this whole thing sound genuine? i mean he was getting the sex anyway so why go through all the hassle? or did he just realize shit this is going nowhere and distance is a bitch. i also thought maybe he met someone else or something. i dont know. im just a little weirded out by the whole turn of events. maybe in a different time and place.
    Sorry for the long ass essay, plz help! it feels good to rant.

  6. hey Dr T, could you elaborate more on “many of us tend to know our long term plans for a girl very early on. We know how far we’re willing to let this thing go before it’s past the point of us being into it.” how would u determine these plans ? based on what ?

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