Reality Steve

Dr. Reality Steve

Podcast #10 with Special Guest the “Possessionista” Dana Weiss Along with “Dr. Reality Steve” Emails

Dr. Reality Steve

Hello there!

So a little back story first.

Back in 2012 I first met my friend, Chris, when I got hired to work at the same place he did. We never really talked or hung out, but had the kind of relationship where we would play bicker while on shift together. That summer we started hanging out a little more mostly because he got promoted and we were always working together. We were both engineering majors so we realized we had a lot of classes together. This led to us hanging out at work, in class, and to study.

As time went on we got closer and closer. We were basically hanging out every night even into the early hours. At some point, I started staying over at his house and eventually started sleeping in his bed. We cuddled, but nothing else ever happened. If I had to go back and describe it now, I would say we had a purely emotional relationship (besides the cuddling). At the time though, I seriously thought we were just best friends. I would talk to him about guys and he would talk to me about girls. But when I look back at it now I see why we were the subject of everyone’s gossip. We were always together, I stayed at his house, he came on family trips with me, and I would go visit with his parents.

Then in 2015, he start dating a new girl. It was really hard to adjust to. I was especially irritated because he had kept it a secret from me, “to prove we could still be friends.” I found out in the middle of a night club and was very upset. Looking back at the time line I know we slept in the same bed and cuddled when they were official (I had no clue). This made me even more upset, but he would just be an ass when I tried to talk to him about it. Life went on, I was sad, but I figured it out and adjusted. We were still trying to be friends and I would even hang out with his girlfriend.

A few months into their relationship, his girlfriend travelled abroad. Chris wanted me to step in and be that emotional girlfriend for him, when he couldn’t talk to her. I started to and then realized what I was doing. It came to me that if I felt so crappy so maybe whatever I was doing was wrong.

In time I was happy it all happened, because I hadn’t realize how I had treated my friends or even myself. That relationship was really toxic for me. I realized I shouldn’t have been bending over so far I almost broke my back for any man. I had a long talk with my best friend and I could finally see the whole picture. I felt like a complete idiot. I took a step back and distanced myself. I didn’t talk to him for quite a while and when I did it would be a very short conversation. After a few months, we both instigated or at least tried to form a new type of relationship. One that was purely a friendship, but it was really hard. I’m still working on it, but I feel like sometimes he still crosses that line. Maybe I’m just overly aware, because I never want to go through that again.

So I guess my question to you would be…

Is it in my best interest to try really hard to work at this friendship or is it just a bad idea all around? I love the guy like family. He knows so much about me and can be very supportive. I love when the friendship works, but should I have to be trying so hard to just be someone’s friend? I’m not sure if we could ever fully move past everything and just be friends. I think the only way we could do that is to have a full conversation about all of our feeling and everything that happened. I just do not believe he will ever do that. He has dropped a few things here and there like oh I tried to kiss you then, but will then change the subject or turn it around on me. It’s so awkward because its like I was in a relationship, but I wasn’t. Why are relationships so messy? Haha. I know that I am partly to blame, believe me, but I was young and very naïve. So please don’t judge me too harshly!

Thanks in advance. I hope this makes sense. It is very hard to boil down a 5 year relationship in a semi-short email.

Keep being awesome

Comment: Interesting email. Mostly because I think there are a lot of things you either didn’t tell me, or that are a little vague. And you said it yourself, it’s hard to boil down a 5 year relationship into an email without writing a novel essentially, so I get it.

It certainly is a different relationship where you spent that much time together, stayed in his bed, yet, nothing physical ever happened. EVER? Did you want it to? Did he want it to? Why didn’t it? So many questions surrounding that. I get that maybe you were trying to keep it platonic, but in that situation, people tend to draw closer to another person spending that much time with them, especially when some of those times were as intimate as you guys had. Something’s missing that you never had a hook up, or never discussed it.

Then to find out he continued doing that with you while he had a girlfriend he wasn’t telling you about? I’m guessing if she knew about that, she never would’ve approved, no matter how much he assured her nothing was going on between you guys. And then when she travels abroad, he wants you back as an “emotional girlfriend?” What the hell does that even mean? Maybe it means he wants to talk to you more, but to go back to the way things were? That’s just wrong. This guy is a little off his rocker. I hope you realize that’s not normal.

So what do you do from here? Well considering how miserable the arrangement made you the first time around, I don’t know why you’d even consider going back to that? I understand he’s like family, but unless you have a talk about it and draw boundaries, he’s probably gonna try and get away with what he did before. So unless you lay the ground rules and he listens, which you seem to think he won’t, I’d say as tough as it may be, you need to remove yourself from the situation. It sounds like you want more, even though you never had more to begin with, right? Or was there any hooking up there you never mentioned? And is he still with his girlfriend? A lot to sort out here. But I don’t think for a second you should go back to being his “emotional girlfriend” again if: A) You want more than that. That’ll never end well, or, B) He’s still with his girlfriend. If he’s single, then you either pursue a relationship with him or kinda cut it off, because as you said, this is very toxic.

Hey Steve! I know you’re short on emails this week so here it goes…

In my family, we’ve had a tradition of always getting together at my parents house for Sunday dinner. I am the youngest, with two older sisters. We used to be very close, but ever since I purchased a home (one sister lives in a condo owned by her husband’s parents, and one sister lives in my fathers second house) I feel like I never see them anymore. My husband says it may be jealousy, and that’s why I’ve been outcasted. My sisters hang out a lot together, but I am no longer included or invited. At first I thought it is because I’m a bit further now (my parents house is about a half hour drive) but one of my sisters is about a 10 minute drive away from me, so that doesn’t make sense.

Needless to say, the drifting never really bothered me. My best friend has always been my mom so I’ve stuck close to her. We email each other daily and I still go every single Sunday. Problem is, no one else comes on Sundays anymore.
I feel bad for my parents because they are in their late 50s and already depressed that their children don’t come to visit, and they don’t see their grandkids as often as they’d like. My mom cooks dinner for all of us that show up, and is constantly saying “well if they don’t come now when I’m offering food, imagine what will happen when I need taking care of”. I’ve pretty much accepted the fact that I will be the one caring for them in their old age. I feel like my siblings just see my parents as dollar figures, with inheritances as soon as they pass.

Is it my fault they no longer come to Sunday dinner? Is a weekly Sunday dinner too often for a family to get together? What can I do to make my parents feel better?

Thanks Steve!
– A fellow Italian (assuming you’re Italian as your last name suggests lol)

Comment: Have your sisters given reasons why they aren’t showing up anymore? What are they? I think once you get those reasons, you’ll know. I can’t imagine it has to do with you having a house and they don’t. Seems like a real petty reason not to show up at your parents house for Sunday dinner. Maybe they’re busy with their own family stuff. Someone needs to just ask them why they don’t come anymore. This may seem like a stupid question, but, do they KNOW there’s still Sunday dinner every week that you attend and they choose not to?

Obviously family dynamics are different with everyone. And yeah, it sucks when grandparents don’t get to see their grandkids as much as they’d like. But someone just needs to say something to your sisters, whether it’s you or your parents. Get a direct answer. Maybe it’s just they aren’t aware it’s happening. Or maybe they’ve got their own issues. Or maybe they want to do it, but only once a month. Find out why, and then take it from there. You can’t force your sisters to do something they maybe don’t want to do, but at least find out the why first.

Hi Dr. Reality Steve,

I’m 43, single and need your advice. I’ve been in some long term relationships with men but never married. I was on a dating app known for hookups and that was fun but I realized it wasn’t getting me closer to finding a guy to date/marry.

I finally put a profile up on Tinder and that has been hit or miss. My question is how long should I wait before I sleep with someone? 5 dates? 10 dates? Dating is so different now with the ability to just judge someone on their looks rather than a blind date or meeting someone at a bar. I don’t want to sleep with someone on a first date but also don’t want the guy to think I’m a prude. What do you think?

Comment: There’s no universal answer for this question. Every guy is different. And it shouldn’t be based on what he thinks anyway. If he expects you to sleep with him the first date, you don’t, and then he ghosts you after that then, well, he wasn’t someone for you anyway. Do it when you feel you want to do it. There really is no answer that is set in stone for this one. But certainly don’t base your choice whether to have sex with him on the first date on what his opinion will be. It’s your decision to do with what you want. If they can’t deal with that, that’s their issue.

I have a question I am hoping I could get a guy perspective on. A little background – I had a boyfriend for the last two years but we recently broke up. We since have been hanging out and trying to work things out, but are officially not together. (He was the one that broke up with me and it wasn’t a great breakup if that makes any difference) I recently went out and unexpectedly met a guy and we went on a date and it went well. He was really nice, total, gentlemen and I am interested in a second date. My issue is that now with Valentines Day creeping up, they both are asking me out and I don’t know what to do. I really wanted this time to be single, date casually, while also figuring out I can work things out with my ex. Now I feel forced to choose and I don’t feel ready for that. On one hand, if I say no to my ex then I have to admit it is because I have other plans or it will be heavily implied (we have had a don’t ask, don’t tell policy with dating since we ended things). On the other hand, I am really interested in this new guy and I don’t want to ruin chances with him by basically saying no where again it will be obvious it is because I have another date. I know I need to, but I don’t feel ready to decide between trying to make things work with my ex or trying to move on with someone else. Like I said, this all happened in the last week and I wasn’t even really looking to date but it kind of happened and it was really nice. What do I do?! Honestly, I am tempted to choose neither and spend the night at home watching movies with my cats and dog.

Thank you so much for any advice you have on this.

Comment: First thing I’d say is any way you do one of the dates on Tues. the 14th, and another one that weekend? Or both are asking you out for the actual day itself? You said yourself you wanted to date casually and don’t feel you should be forced to choose. Then don’t. No one’s putting an ultimatum on this. You move at the speed you want to move at with either guy.

Obviously I don’t know anything about your situation with your ex and why it ended, but you did say it wasn’t a great breakup. So that right there gives me a little pause in why if you have this new guy who appears you don’t want to ruin things with, you’d still be thinking about disappointing your ex. That’s a decision you’ll have to make eventually, but for right now, you don’t. This just came up, VDay is in less than 2 weeks, and if you feel a little too much pressure, or having to reveal things to the ex that you don’t want to, then you don’t have to. If you want to go out with the other guy, but don’t feel like telling the ex you’re seeing someone new, then just say you’re staying home and don’t feel like going out. Use the ol’ VDay excuse of, “Ugh. Such a made up holiday. Too much pressure. I wanna watch ‘This is Us’ on the couch with Whiskers, Jodi and Hambone’” (Yes, I just guessed your cats and dog name for you. I’m good like that).

You don’t owe either of these guys anything. If you don’t want to go out on VDay, don’t go out. Perfectly fine. If you’re feeling this much pressure already, then that’s probably your best bet.

Send all links and emails to: To follow me on Twitter, it’s: Instagram name is “RealitySteve,” or join my Reality Steve Facebook Fan Page. Talk to you next week.



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