Reality Steve

Dr. Reality Steve

“Dr. Reality Steve” & the Final Live Chat of the Season Tonight at 9:00pm EST/6:00pm PST

Hey Dr. RS,

This isn’t like a major pressing issue, but since you’re constantly trying to drum up questions I figured I’d throw my question in the hat. I’m definitely curious about what you have to say.

I’m in my early thirties, have a great job, and overall I love my life. I have a lot of different hobbies and stay pretty busy but the reality is that I get lonely sometimes. I haven’t seriously dated anyone for over 3 years. I have done the online dating thing and it wasn’t horrible, but it wasn’t great either. I just got tired of investing all of this time online and in person to meet guys I end up having no interest in dating long term. I’ve made some great platonic friends though! My area is notorious for not having a great selection of single guys so I didn’t expect much, but I quickly got to a point where it wasn’t worth the time and energy. Online dating basically feels like job interviews to me. It’s just such an unnatural way to meet someone and there’s all this pressure because you’re meeting with dating specifically in mind. In any case I tried and it just didn’t work out for me.

I’ve always prescribed to the notion that it’s better for single folks to invest their time in doing things they love rather than focusing on dating. Because if/when you meet someone doing something you love you automatically have something in common, there is less pressure and a relationship can develop more organically. But I’ve been doing this for years. I play indoor soccer once a week, go to yoga classes, go out to local events and concerts, snowboard and skateboard whenever I can. I always say yes to invitations to see or do new things. I feel like I’m putting myself out there constantly and I meet a lot of different guys but nothing comes of it. The few times I’ve felt a connection over the past few years the guy was either taken, not interested, or ends up flirting with me but going home with someone else (that happened at a wedding literally 3 weeks ago).

I’m doing my best to just keep living a fulfilling single life and hope that I will eventually click with someone. I’ve gotten to the point where I’m trying to accept that I may never connect with anyone and could spend the rest of my life single … happy and lonely. I know that is kind of irrational but it’s been so long since I felt connected with someone it’s hard to remember what it’s like or to imagine it ever happening again.

So what say you, Dr. Reality Steve? What is a single girl to do? Am I on the right track or do you think my theory is bogus? Should I just shut up and be happy that everything else in my life is so great? I know a lot of people out there have a lot of real problems in their lives and 99% of the time I’m incredibly grateful that my biggest “problem” is being single. But there’s still that 1% of the time that I wonder if there’s something wrong with me or if I’m going about things completely wrong. Anyway thanks in advance for your advice, I’m looking forward to hearing what you have to say.

Single and trying to Mingle

Comment: Well there’s no magic formula to meeting someone. Some people get set up by friends. Some meet at bars. Some meet online or dating apps. It could happen anywhere and anytime. Obviously the more people you date, the better chance you have of finding someone. Or you can be like myself and just date very few people and only invest time into ones you think have potential. I’ve never been a numbers guy in the dating world. Just not my style. But I’m single, so that obviously hasn’t worked as of yet. I still wouldn’t change my approach. I’d just never be comfortable dating as many as possible and hoping to find one.

I think most people who are single for a while will always come across the “maybe I just never will find the right person” phase. I’ve certainly thought it a few times. Would I like to meet somebody? Sure. I’m just not gonna force it. So you’re not doing anything wrong, and there’s nothing wrong with you either. It’s just through a variety of factors, you just haven’t met the right person yet. I know, sounds cliché, but it’s true. If you had, you’d be in a relationship right now. So my suggestion is to enjoy what you have going on, don’t force anything that you don’t want to, and eventually I guarantee you’ll meet someone you connect with. Doesn’t mean you’ll run off and get married, but baby steps first.

Hi Steve! Figured I’d give this go and get some unbiased input.

So the guys I have really liked in the past and continue to be drawn to are confident, very fun, funny (witty), well spoken and quite intelligent. These are the types of guys I may ‘date’ very briefly and much to my dismay (with the exception of just a few) always demonstrate they are uninterested in having anything long term with me, thus leaving me single for many years.

Fast forward to a few years ago. I moved across the world to start a PhD. Still single. Continued looking for the same type of guy I always go for (can you blame me?!). Went online dating and instead found this really sweet, kind, ambitious, very intelligent guy that I got along with really well. We started dating and continue to this day.

Here is the thing- he is socially awkward. Not funny at all. It’s actually kind of funny how unfunny he is. He grew up in a secluded town and was home-schooled, which I’m sure led to his awkwardness. He barely has any friends and because he is so awkward I find it easier (less pressure on me) to just keep my friends separate from him.

However, he is so nice to me. We have the same outlook on life and completely on the same page with future plans. He supports me in everything I do and plan to do. He does tend to agree with me but I know he will disagree when need be. When we are together, life is nice. It’s not exciting, but instead cozy and pleasant. He is so knowledgeable that I love to talk to him-but it is usually me pushing conversations as I am much more of a talker. I love to travel and have adventures and he is always up for doing these things, but it’s usually more my ideas and he would go along.

We rarely fight but at the same time rarely have these magical times as well. Everything is sort of neutral which is something I am not so accustomed to. I am passionate, super fun loving, silly, and outgoing. When I am with him I am just dialed down. I, myself have become more neutral I suppose.

I say I do not need or really want to get married, and it is true but I do wonder if it is because I am not dating someone I passionately and whole hardheartedly want to get married to. I also wonder if me not really wanting to have children has to do with not finding a partner I would LOVE to procreate with. (my justifications for not wanting either do not point to that.. but I just wonder).

At 26 or even 30 Id tell myself to see how it goes for a bit. But I’m now 35, friends back home are all married with children and tied down to a huge mortgage payment in a suburb. Although that is not the life I SAY and THINK I want…it is the time I need to really make a decision if I do not want that or not.

I’m at a loss. I do want this ‘fairytale’ love that I see and hear about..but at this point, is respect, stability, opportunity to achieve any goal I can imagine (yup he’s that supportive), consideration enough for a LIFEtime? Especially when our future will likely be just me and him. (I do have very close friends and family but they are all so far away-and I am not sure I will every permanently live there again).

What do you think? Break up to search for passionate love with someone fitting the description of what I have always wanted (even though they never seem to want me back) OR stay with the nice, pleasant life I have created for the last few years?

Thanks Steve.


Fairytale or bust

Comment: Do you think this “passionless” relationship with someone who doesn’t excite you all that much will sustain? I don’t know. I’m not you. My guess is it won’t, but that’s just me. By the sounds of it, it looks like you’re kinda settling and little bored by it all. And maybe just the thought of starting over, getting out there again in the dating world, meeting new people etc just doesn’t appeal to you because you seem to be complacent with your current guy. I’m glad there isn’t a whole lot of negativity in your relationship, or some of the stuff you read here on a weekly basis, but being with someone you’re not all that excited about, in my opinion, will wear thin after a while.

Not saying go dump him tomorrow, but you said you keep him separate from your friends, and that if there was a future with him, it’d pretty much just be the two of you because of where you are located and such. Do you really think you want that to be the guy you possibly spend the rest of your life with? I don’t know. I just get the sense you’re already trying to talk yourself out of him. I think most people when in a relationship wanted to be stimulated in every way possible by their partner. It doesn’t sound like you are.

But first I do think you need to decide for sure what you want out of it all, and relationships in general. Like you said, you need to make a decision for sure if that’s the life you want, or if there’s still a possibility you’d want kids, etc. Once you make that final decision, I think you’ll know what you need to do with this current guy.

Checkin in for a doctors appointment!

My boyfriend and I have been together for 2 awesome years. We went on a trip this last weekend that knocked a few things off our bucket list and really just brought us closer together. We’ve talked about seeing a future with one another and not wanting to be without each other, but haven’t really gone into a lot of specifics. Just let things happen as they have. He told me yesterday he thinks we will be together for a long long time. My heart soared, after being in an extremely manipulative and abusive relationship I have never felt such an awesome love like this before. I have no doubts we have a bright future ahead!

I am writing because I don’t want to be overbearing. How much is too much? I want him to know and see how loved he is, but I don’t want to go to over the top. We are around your age, and so from a male perspective (I know you are all different) what makes you feel loved? And what makes you feel like your SO is being way way too clingy?

Any and all advice would be appreciated!


Comment: Well the trip you just took is a huge one. And it sounds like he’s pretty invested, so that’s a huge start. But what works for me might not work for him. I wouldn’t get too carried away because you have a good thing going. I wouldn’t change anything based on what he said. I don’t know if you guys live together or what, but if you don’t, maybe that’s the next logical step after 2 years?

This was an email that didn’t talk about what her boyfriend doesn’t do or anything negative, so that was refreshing. Keep it going. I don’t know how much you guys see each other, but it sounds pretty solid for 2 years and he said he can see you together for a long, long time. Can’t beat that. I’d move in together if you haven’t, but if you already are, or that’s not an option, then keep spending time with him. Go on another trip. Surprise him with a dinner. Or a getaway weekend. Seems like he knows you’re invested too, so, don’t overthink it and just go with the flow.

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 tonight.

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  1. rob22

    August 25, 2016 at 9:26 AM

    Miami: To go along with what RS said, there’s no way he would have blown off the musical festival where he could have seen you if he was very interested in you. He would have found the money if he couldn’t wait to see you. There is nothing there. Treat it that way.

  2. xnuzboss

    August 25, 2016 at 9:38 AM

    Dear New England Mother,

    The essential conflict expressed in your letter is something everybody experiences as life marches on, and that is the need to grow up. When children enter the picture especially, it’s time to set aside childish things, and that includes spending time with college buddies. Maybe your husband needs to embrace reunions and put aside the wish to hang out as a college guy in perpetuity. That’s one issue.

    Parents and in-laws becoming increasingly important as children come on the scene and especially as they get older. There is a special and necessary bond between a young mother and her own mother when raising children, and I encourage you not to be afraid of that and to make darned sure that your husband is aware that it has nothing to do with him or his parents. It’s simply a necessary part of being human.

    That said, I feel that the onus on visiting is with the grandparents, because this isn’t about them. It’s about you and your budding family, and there are always options for people who can’t afford the expensive travel. New England is beautiful in early October, and that should be an annual trek for them. If they can’t make it, resist the feelings of guilt, for your wellbeing is more important to you as a mom than theirs.

    Finally, given what you’ve said, I’d most strongly mention that vacations are for the people who get them, not to satisfy or assuage your guilt. You three need to put yourselves first in this area, ‘lest it become too easy to put yourselves last in others.


  3. rob22

    August 25, 2016 at 9:55 AM

    Single and Trying to Mingle: I went through this too. I was definitely not interested in “just getting married”. If it wasn’t a person that I had a lot in common with, I wasn’t going to sign up for 50 years of that. At a certain age, all of my friends got married & they kinda made me feel like I was doing something wrong & was way too picky. So, at that point, I started to think it wasn’t going to happen. But, I kept just doing what I was doing. I did date a lot and definitely kept open to all possibilities. I think that was the key. 95% of the women I dated never got past a date, or two. But, then I met my wife. I was doing an activity I loved, and we just ran into one another. We’ve been married 25 years now. So, my advice is to just open to anything and anyone, say yes to dates, keeping doing the activities you love and it will happen eventually. I think we put time tables on these things and life doesn’t work that way. Things happen during different time frames and in different ways for different people. Things are just taking a little longer for you.

    Since you haven’t dated in three years, that says to me that you haven’t been completely open to dating. And the fact that you gave up on online dating backs that up. The only way to lose in life is to give up. Three years not dating feels a bit like you’ve given up. Time to get back on the horse. It’s scary, I know. And you’ll have a lot of lousy dates, I know. And you’ll meet a lot of guys not interested in relationships, I know. But if you stay at it, you’ll meet someone who IS really interested in you & does want something more than a hook up. It will happen for you. The early 30s is too young to be giving up…. and yeah, I know when you’re that age it starts to feel old. It’s not. Trust me.

  4. rob22

    August 25, 2016 at 1:44 PM

    Fairy Tale or Bust: You’re not wrong for not wanting to settle. You shouldn’t settle. And, I can’t tell from your note whether that’s really what you’re doing…. Because you brought up “The Fairy Tale”.
    I say this because The Fairy Tale is….. well….. a Fairy Tale. We might get married to someone we fall head over heels about, hyperventilate thinking about and are just hugely attracted to. But then life happens. Our spouses have annoying habits. Our spouses gain weight or start to noticeably age. The things we used to find funny become really irritating. And if they tell that damned story one more time!!….or if they leave the bathroom door open while taking a dump again….!!!
    So, then what do you have after the Fairy Tale goes bust? Well, if you have a shared world view (including religious views), shared values, a shared idea about having kids & how to parent them and are interested in many of the same things, you’ve still got quite a bit. The heart going pitter patter….eh…. not so much. That’ll come and go. It might take long vacations too.
    So, here’s the deal. Love is not a feeling. For those that believe it is a feeling, they will eventually fall out of love. Because their spouses aren’t always going to be on the positive side of their feelings.
    Instead, Love is a verb. You choose to love someone, or you choose not to. If you choose to love them, your feelings will come around. If you choose not to love them, well, not so much. They’re toast.
    That’s not to say that you should marry someone who you’re not attracted to, or who’s awful in bed, or who bores you to tears. No. Not saying that. You have to have a relationship you’re happy with or it’s going to be a long 50 years. But the fairy tale & heart going pitter patter stuff. It’s very overrated. Unless, of course, you’re looking forward to a very close relationship with a Divorce lawyer for a couple of years.
    Evaluate whether your boyfriend is someone you’d want to spend the next 50 years with. Then choose to love him, and your feelings will be fine. Or, choose not to love him & move on. It feels like you’re playing somewhere in between right now. Make a choice & commit to it one way or the other. It’s the best way to go.

  5. LM111

    August 25, 2016 at 5:03 PM

    Dear Fairy Tale,

    I’m going to give you the same advice that my mom gave me when I was dating this great guy (on paper) who adored me, wanted the same things I wanted, had a very successful business, and wasn’t funny – at all. The guy was hinting around about engagement rings and I felt a tinge of anxiety every time he brought it up. But, he was very sweet to me and I DID want to get married… someday.

    My mom said: It’s simple. Throw out your checklist and marry your favorite person to talk to. Imagine that you had to drive across the country, who would you want in the car with you for that trip? Who could you have fun with just going to the grocery store? Marry that person. Dishwasher or Doctor, doesn’t matter. You only get this one life… make sure you have fun.

    I knew right away that marrying him would be a mistake. Ended it and never regretted that decision. I’m not saying that’s what you should do. Just giving you something to think about. I also agree with everything Rob said.

    Good luck to you!

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