Ask Dr. Tony Vol 16

What’s up? The doctor is back with that advice that will one day save your life. Well, not really but perhaps I can at least give you some perspective on your shitty love life. As always, I’m not a licensed anything but I do have an uncanny ability to give you the honest truth (as I see it) in respect to your romantic debacles. If you have more relationship questions, email me them at Send them whenever as I’m always taking submissions.
Anyway, on with this weeks bag of issues.

ok, here’s what i’m dealing with….i was in a relationship with this girl from a little before new years until the end of march. we were started off as friends of friends until she sent me an email that said she wanted to hang out exclusively. at first i was on the fence, bc i wasn’t entirely attracted to her, but ended up hangin out with her anyway. she’s a cool chick! great taste in music, outgoing personality, really sweet….well, we ended up smoochin and cuddlin after a month or 2 and started dating. she became really attached, said how much she was falling for me, and was always very affectionate. i’m a little wary about falling for people so quick, so i wasn’t as into it as she was….but as time went on i felt myself drawing closer. SO here we are, luvvy dubby and shit for a few months, things are going swimmingly…i like her a lot at this point (really close to loving her)….until one day she decides she isn’t happy with me. it seemed completely spontanious! she literally uttered those words “i love you” for the first time just a couple nights before introducing this epiphany to me! needless to say, she broke up with me a few days later and i was left heartbroken. we didn’t see or speak to each other for about a month. we hung out together w/ some mutual friends one day, and that was ok. we didn’t interact so much, but i was fine with it. i think about her a lot tho, and i told her (my intention wasn’t to get her back). and she gave me the usual “chinup!” rundown.
so here’s where the situation gets a little sticky….we have a mutual friend that was moving to michigan, and i’m pretty tight with this dude. he hung out at my place a few days before he left. well, apparantly, my ex moved WITH him! i found out a few weeks after the fact from somebody else. i was shocked, confused, hurt, upset, and most of all just down right pissed off. i kind of went off on her and said some things i probably shouldn’t have said (quote: called her a heartless bitch) and it’s just been boggling my mind.
so here’s the question… i have the right to be mad??? i kind of feel like an asshole. from an outside perspective, they’re doing no wrong. they’re both really happy in a new place, and that’s a good thing. all’s fair in love in war, right? but people still get hurt. i’m hurting pretty bad. i was thinking about calling him mono-a-mono to just talk about the situation. i’m very pro Bro’s over ho’s, but that’s kind of a dick thing to do to your homie, aint it? and also i should be happy for my ex because she’s happy, right? BUT she did kind of fuck me over….twice….2nd time feeling a little worse than the 1st…. i don’t know dr. Tony, how would you feel??

Dude, you have the right to feel however you wanna feel. If you want to never talk to either of those people again, you’re justified. If you want to be the bigger man and just move on without making any drastic declarations about how this all hurt you, then you can do that too.It really depends if you’re a grudge holder type. But regardless of that, you 100% have the right to feel like you got shit on here. There’s obviously more to this story than you know and I’m guessing, if you found out, that stirring of rejection and anger will probably explode into full on rage. Something isn’t sitting right with me about this and all I did was read two paragraphs.

If this girl was THAT serious about you, something pretty intense must have happened for her to just drop everything and bounce with that other dude. I don’t wanna say that kind of thing is unheard of but it’s certainly rare. That is, of course, unless there’s more of a history between the two than you are aware of. Whatever it is, it’s gonna suck when you hear the truth about. But beyond that, you might of dodged a bullet cause any girl willing to drop everything and move all of a sudden is lacking in some serious logic and definitely is only thinking about herself.

I’m all for being the bigger man in this situation but no rationalizing of “bro’s before hoe’s” is gonna make you feel okay about this. You got played. The only way you should feel is shitty.

I’m in my late twenties, been in a relationship for over four years and it’s something I definitely could see turning into marriage. I’ve never been a socially awkward guy and never had an issue talking to girls, I also know I’m a good looking guy at least at this point in life before time and alcohol catch up to me. The Girl I’m with is cool, hot, and shares a lot of similar interests with me as well being able to hang out with the guys and not be annoying, not to mention being able to put up with me being a moody bastard.

Long story short, before my current relationship I had dated a girl for quite awhile, was a complete mess of a relationship that drug on too long (Last yr of high school-First couple years of college) and about half way through college I broke it off. I had a good year and a half as a single guy before hooking up with current girl and never thought much of it. Even when I was single I would hook up with girls but for whatever reason I never really went too far with any of them (except for one 1 night stand) even though I easily could have. Basically once I figured out I could hook up with the random girl I lost interest and most of it didn’t go much further than making out, etc.

After doing this for a awhile I started dating current girl and for years as far as I was concerned I had a pretty awesome relationship and never considered the fact that I should be out slaying hoodrats or else I would be filled with anguish and regret in my later years. Most of my friends (maybe cause I live in a major city?) are similar to what you’ve described, they’ve hooked up with a ton of girls (though my friends have zero standards and have banged tons of more than questionable broads that I’d never even think of hooking up with if I was single)

So considering this long ass, novel like story, is there something wrong with me and am I gonna horribly regret this decision later in life? Should I get out of the relationship now and hook up with as many girls as possible or something? I definitely see the appeal of the other side, but I’d hate to throw away something great for just random hook ups. At the same time I don’t wanna be one of those guys who ends up cheating on his wife/girlfriend constantly because he feels like he missed out on something when he was younger.

It’s clear you’re a relationship guy. You’re not the same breed as a typical guy who just wants to get his dick wet. Because of this, I don’t see any reason to break up with a girl just to sew your wild oats. Your oats ain’t that wild, bro. Sure, there will be times when you’re married and bored and all you can think about is that girl you should have fucked but the reality of it is that you’re not that type of guy. And, in my experience, guys like that don’t do well under those “single guy” circumstances. They fuck a few randoms, are never really comfortable with it and end up settling down with someone fairly quickly.
Put it this way…You know those types of girls who ALWAYS have a boyfriend? Like they break up and then talk about how excited they are to be single but, within a month, they’re “In love” again? You’re the guy version of that. There’s nothing wrong with it but you can’t turn that into an international playboy. Honestly, you should be relieved. Most dudes I know in relationships , regardless of how many girls they bedded prior to that relationship, are in a constant state of regret about what could have happened and what would be happening if they were single. To not have that as a prominent thing in your life, I’d say you’re one of the lucky ones.

I am sending this super late b/c I LITERALLY cannot sleep…I’m shook.

(I’m gonna try & make this as short as possible)

Ok, so I’m in a committed monogamous (to my knowledge anyway) w/ the most amazing man. Nigga is perfect and I am totally in love w/ him.
Anyway, I just recently met his friends. Well, turns out I used to fuck one of his best friends…often. This was roughly 4 years ago.
His friend was visibly like “wtf this bitch” when he saw me, but he didn’t say anything to me or my SO about our fling or w/e you wanna call it.
I did not know they were friends & honestly, if I had known they were friends…I would’ve never gotten involved with my SO b/c being known as a homie hopper is not the move you know?
I’m one of those honesty is the best policy type of chicks BUT I know how men’s egos/pride are & all my guy friends are like “don’t say shit” or “he gon dump you yo, I would dump you” or if he asks you, “deny deny deny!”
Obviously, my question is should I tell my SO or carry the secret to my grave?
And how should the conversation go? Should I have a convo w/ his friend first or should they both be present?
If you were in this situation, would you want to know/would you forgive your girlfriend?
Your advice is greatly appreciated!! ❤

This is tricky cause there are a lot of variables. Is the current man the jealous type? Some dudes are either totally rattled by shit like this or it doesn’t phase them. If he seems like the type who would be horrified by hearing this, I suppose you can’t really tell him. However, if he’s not a bitch made , insecure kinda dude, than it might be for the better cause , if you guys stay together, he might find out on his own eventually.
I’d say you should contact the friend and fuck him more…just kidding. But I do think you should contact the friend and ask him what he thinks. See if he’s comfortable with it. If not, than you know it’s a secret that will keep and it’s safe to lock it away. If he’s okay with you telling him, then you should do it. It’s best to just air that kinda thing out sometimes.

Just a word of advice, if you do tell him, be mindful of how you do it. Don’t make a huge deal about it. The more of a “I have to tell you something serious” moment you make it, the harsher is gonna seem. I’m not saying just mention it in passing but downplaying it is the route to go. If he wants details, be vague. He doesn’t need to know you fucked the dude 59 times. Just assure him that it was a long time ago and he’s all that matters now.
You’re right about male insecurity and beyond telling him about how his friends dick is bigger, something like this will inevitably tap into his ego…you just gotta hope he’s the type of dude who can handle it. But, considering this all happened before you knew him, if he gets really upset, fuck that dude. If he cares about you, he will just accept it, deal with it and move on.
No guy should be naive enough to think there were no dicks before him and no guy should get mad at those dicks as long as they remain in the past. If he cares more about his pride because someone he knows also had sex with you than he does your relationship, it’s a pretty shitty relationship.

So I crossed the forbidden “friend zone” line. I’ve been friends with this girl for 7 years. We did everything together, all the time. We slept in the same bed many times, but never cuddled or anything like that, mostly just tickling and play fighting. I always wanted to kiss her, but never thought I would and I was completely fine with being her best friend.

Last winter when she came home for the holidays is when things changed. One night we went to a club, where my car was broken into and her laptop was stolen. All her pictures and 400 gigs of music was lost (I told her all the time to back that shit up). She was vulnerable and I was there to comfort her. We ended up going back to my house, split a bottle of wine and just cuddled all night. We both knew things changed between us, but I still didn’t really think anything would happen between us.

Then last week, we were hanging out and when she left we flirtatiously alluded to us being together through texting. I kind of took this as my “in” to make a move. Two days later I was at her house. When I had to leave, I called her outside to say bye. I walked up to her and put my hands on her face, but she pulled away because her front door was open and her dad was watching t.v. close by so we went out more. She was saying this is too quick and she wants to go slow. I said we can start slow with a kiss, so she pulled her hair back and lifted her chin and I kissed her. I left right after, she then texted me she was COMPLETELY SHOCKED and had no idea what just happened. She was flustered and said no one has ever surprised her like that.

Later that same night at about 10 she asked me if I wanted to get a beer with her. So, we met at a hookah bar and smoked and drank. We acted as if nothing happened earlier that day, we were laughing and joking just as much as ever. We left and went to Taco Bell to eat and hang out in her car. At about 3am I decided to get out and “leave”. I went to her door and opened it. She knew what was coming and was hesitant. She was nervous, so I pulled her out and we kissed again. We ended up making out in the back seat of her car till 6am. We both thought this is crazy and the one thing you’re not supposed to do with your best friend. She’s nervous and scared about this whole situation, and I have no idea how to handle it because I’ve never even seen others in this predicament. Both of us haven’t been in serious relationships in about 4 years.

This is completely new territory for me and my plan is to just go as slow as she wants and not force anything. Or should I? Should I wait for her to figure out what she really wants?

50 shades of grey ass dude…Those make out descriptions were HAWT!
This is a tough one cause I don’t get a 100% feeling that she’s signed on for the ride. Granted, I’m just going off what you wrote but her hesitance makes me think she’s mulling it over. This could honestly go either way. I get it though. As close friends , turning a friendship into a relationship is tricky. It could all backfire and you’d both be out of a friend…but, on the same note, it’s kinda impossible to truly be friends with someone who you desire more than just a friendship from. I mean, you can do it, but there will always be that cloud of rejection and inequality in the relationship.

Because I feel like she’s undecided, you should definitely take it slow. As slow as she wants you to take it. I’m guessing she needs to get her bearings and figure out where she stands in all of this. The shock of you actually viewing her like that and not just your pal probably confused her a bit.

All in all, be patient but also don’t get your hopes up. The friendzone transition is never easy and rarely works out how people envision it to. Also avoid Taco Bell if you’re gonna be hooking up all night.

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