Reality Steve

Dr. Reality Steve

“Dr. Reality Steve” & Live Video Chat Returns Tonight at 9:00pm EST/6:00pm PST

Dr. Steve,

Hi, hope you’re having a blessed day and hope you can help me out with this situation I’m in.

Back in high school when I was a junior (2001-2002) I was dating a guy for almost the whole school year. Anyway, we broke up. I hadn’t really talked with him or seen him since we broke up all those years ago. He had gotten married.

Anyway, he’s going through a divorce and is now on dating websites. He saw me on match .com and he connected with me there. He could have tried to look me on Facebook , but I go under a different name on there. I use my first and middle name.

Anyway, he asked to meet for lunch to catch up. Now I have no interest in ever dating him again. I know it’s not like it’s been a few years since we have seen each other, it’s been over a decade and maybe he does just want to catch up. However, lots of guys I know have always said it doesn’t matter how long a guy has seen an ex if he wants to meet up to catch up, then it’s because he wants to see if there could be a chance he could have her back.

What are your thoughts? Do you think he honestly just wants to catch up or he wants to do more than catch up?


Comment: Every situation is different, but there certainly is some merit to that. I don’t know the guy so I can’t begin to tell you want his intentions are. However, he obviously is familiar with you and you have a past, so it is a little easier to ask someone out that you know as opposed to a stranger. You won’t know what his intentions are until you go out with him. I’m sure a part of him wants to catch up to see if something else is there. That’s natural. If he does, and yet you have no interest in that, then just let him know. If it ends up being just lunch, then hey, you got a free Asian chicken salad out of it (I’m just assuming that’s what you’ll order based off absolutely nothing other than you’re a female).

Hi Steve,

Thanks for the spoilers & I`m so glad to hear that Kaitlyn is the next bachelorette!

Anyways, here’s my question. A few weeks ago (Feb 6) I went clubbing with some of my friends. I danced with a guy there that was pretty sweet and seemed pretty genuine (except the part where he asked me for a kiss and I refused because I don’t really go around kissing random people, but now I regret it). I felt like we had a good connection since I got to know him a little and he got to know me. I asked him where his friends were and he said he didn’t care because he was dancing with a pretty girl. At one point my dress kept riding up since it was pretty short and he helped me pull it down (instead of pulling it up to show more leg, so I thought it showed character). He thought I was joking when I told him I was single. He asked for my number (and told me not to give him a fake one) and I gave it to him.

Later on that night, he texted me and asked if I left already because he wanted to dance with me some more. He asked for my Instagram and since I was beyond drunk, I didn’t think it was that big of a deal so I gave it to him. I`m 23 and single so its not like I had anything to hide (he’s 24). But now that I’m sober, I look back upon the texts and I wonder why he kept asking for it? Like, he asked me for it and then he asked me why I haven’t accepted it.

I wanted to play hard to get and so I didn’t text him for a few days because I wanted to see how interested he was (or lack of interest). A week later I still didn’t get a text from him so I decided to reach out to him. We made some small talk but the conversation ended since he was giving a tour of the city to his dad that was visiting.

A few days later (this past Feb the 20) I texted him again just to show that I was still interested. We talked a little and he was playing beer pong, so I told him to text me later with the winking emoji because I wanted to leave it in his court to see if he would text me.

So basically, its close to being a week since we’ve talked, but he liked some pictures on my instagram that I posted. So what does he want from me? Was he just drunk that he was interested? Or do you think he lost interest? Or maybe he doesn’t think I`m his type anymore? What should I do? Should I just drop him or text him again? I don’t want to annoy him….

Comment: Man, the trials and tribulations of early 20 somethings. What a horrible, disastrous situation you’re in. I hope you can pull yourself through this.

So you’re asking me about a guy who’s liking your Instagram pictures but not talking to you? This is a thing? I’d say he’s a 24 year old horn dog that wanted to get in your pants at the club, and the second you left, wasn’t really interested anymore and probably moved on to someone else. This game playing on text and Instagram over the past couple weeks is silly.

Dear Reality Steve,

My ex broke up with me a little over a month ago. I hadn’t made any contact with him whatsoever on my behalf after the break up. He tried calling me about a month after the breakup, without a voice mail or text following the missed call. I didn’t return the phone call or try to message him, I simply ignored it. About five days after that, I received an extremely confusing text message from him. He said that he had received a letter from me in the mail that he didn’t realize was from me when he first opened it. He asked me what it was about. I NEVER sent him a letter ever, not even when we were dating. I’ve never been more confused about a text message. I asked my family if they had ever sent him anything even though I know they don’t know his address. I’m so paranoid over it. I decided to ignore this text message as well because I feel like it could be a trap. I’m wondering if he was trying to get me to respond to him by making up some crazy story because he was mad I didn’t answer or return his call from a few days earlier. I also pondered whether his family or friends would send him something as a joke or to confuse him, but after meeting his family and friends and them seeming normal, I would like to think they wouldn’t do something like this. What do you think this could be? Have you ever heard of a guy making up such a bizarre story to get an ex’s attention? I feel like someone is doing something fishy whether it is him or someone else, I don’t feel like it would simply be him confused over a piece of mail he received, knowing from my own personal experience that I’ve never been confused over mail I’ve received. Thank you for your help Reality Steve!

Comment: Absolutely 100% he concocted a BS story to get you to get in contact with him. I’d ignore it. Yes, I’ve heard of this situation before, but the other way around because it happened to me (just not with an ex). However, multiply that by 1000 and that’s what I had to deal with. He’s making sh** up to get you to talk to him. Don’t give in.

Dear Dr. RS –

Sorry in advance – I think I missed the deadline for today but you can include it next week instead. This is going to be a long one…

This past September I discovered my boyfriend of 5 years, who I was living with, was cheating on me for at least the 2nd time (that I know of). I immediately packed up, moved out and never looked back. I shouldn’t have forgiven him after the first time but I thought we could make it work. Obviously not. He’s a loser and will probably die alone (side note – he was “middle-aged softball guy” to a T). About a week after I moved out, I received an email out of the blue from a guy I met on vacation when I was 19 (I’m 31 now, just as a frame of reference). Turns out, he lives 45 minutes from me. We went back and forth a few times with long emails, catching up on each other’s life. After a few emails, he revealed he had been dating a girl for the last 6 years, things had fizzled and he didn’t think she was the one. He was currently living with her and unsure how to go about breaking up with her. I was disappointed to hear he had a girlfriend, since we always had some sort of connection but kept my distance given my own situation and never would want to be “other person.” We met for drinks a few times to catch up, enjoyed each others company but kept it very platonic.

After meeting up a few times, he revealed he really liked spending time with me and was planning on breaking up with his girlfriend soon and moving out of their shared apartment. He wanted to continue to meet for brunch, dinner, whatever. I couldn’t have been happier to hear that but again, reminded him that until he was out of his apartment, we would not be crossing any lines and were strictly friends.

Over the holidays, things really began to pick up, texting daily, calls from him to say goodnight, etc. He told his family about me, said how they couldn’t wait to meet me. He finally moved out of his shared apartment in January and could not wait for me to see his new one. The first time I went to see it, things were a little awkward but we had a nice time hanging out. I had expected him to finally kiss me but he didn’t. Next time we hung out, we decided I would stay the night at his apartment. He finally did kiss me, but just a few times and did not try any other moves or anything. We cuddled and that was basically it. I was a little confused but assumed he was just trying to be respectful. Other than wanting a little more action, things couldn’t have been going better. We both felt a deep connection to each other and things seemed be going great.

We had lunch together on Valentines Day, hung out the rest of the day, I stayed the night again. No action but I just thought we were taking things really slow. I left the next day feeling great about things. He on the other hand apparently took a 180. A few days later he told me he needed some space and he felt like he was rushing into things too soon after just getting out of a relationship. This was the first time he was living alone in his life and needed to figure things out and adjust to things. This caught me completely by surprise since from the beginning he was pursuing me. He said he still wants to hang out sometimes but for now needs to take step back.

I feel like I am in the twilight zone. I understand him needing time but shouldn’t he have thought about it months ago when he was asking to see me 1-2 times a week and calling me every other day? Was I just his crutch to help him through his breakup and move? What the heck happened? Is it weird he didn’t try to do anything more than a few kisses (not even tongue!). Please help make sense of any of this.

Dazed and Confused

PS. Love the 3x week doses of RS – breaks up the work week nicely!

Comment: Another “Dazed and Confused?” Really? How about Dazed and Disappointed? You all suck this week on your alliterations.

It definitely seems pretty extreme, but to his defense, it was a girlfriend of 6 years he had. You say “shouldn’t he have thought about it months ago when he was asking to see me 1-2 times a week?” Sure. But until he saw you those times, maybe he didn’t realize he wasn’t ready. That’s what it sounds like.

I do think it’s weird that you guys did nothing physically and he’s pulling back. Seemed it’d make a bit more sense if you guys actually slept together and moved to quickly and then he was like, “Woah. I’m not ready for this.” But yeah, that is weird. However, what I find a bit more weird is a guy you met on vacation 12 years ago just randomly sends you an email after a 5 year relationship just ended? Were you friends on Facebook or something and he sent it? Or he just remembered your email? How did this guy find you? Seems kinda creepy. Unless you were FB friends and he was just following your status updates and could tell you were single (or was at least hoping), random dude from vacation 12 years ago emailing you out of the blue to ask for you help regarding HIS relationship situation is totally bizarre.

I would just respect the guy’s wishes and take a step back. Although considering the pace you two are on, it’s basically like you’re in a 5th grade relationship now. How interested in this guy are you? Are you ready to get back into something after a 5 year relationship ending? Keep in touch and see where it goes with him because he really could be telling the truth about not wanting to move so fast (even though fast isn’t really fast nowadays). Six years, he’s finally on his own, you’re the first girl who stays the night since his ex, I mean, I can see how he could get freaked out. I think he’s in the minority of guys like that but he definitely could be a little freaked by it.

Hi Dr. Steve,

First of all – I love your site! J I’ve been a loyal reader since Jake’s season and can’t even imagine how many hours I have spent on your website since. Thank you for all that you do.

I’m trying to get a guy’s point of view on my situation – I’ve been dating my boyfriend for 2 ½ years and our relationship has been better and easier than I ever thought a relationship could be. I know he adores me and he treats me incredibly well, so no issues there.

We’ve discussed it and known for about a year that we will eventually get married. I’m coming up to the point where I’d like to get engaged at some point this year – we’re 26 years old, both have great jobs in our chosen careers and I hope to buy a house by early next year. I’m sick of my money going down the drain in rent. I am not comfortable buying a house together unless we are well into an engagement or married (just my personal values). If we pool our money together we could afford a much bigger down payment and save thousands of dollars on insurance. To be clear, I definitely think we as a couple are ready to be engaged, but this house thing gives me a greater sense of urgency than I would otherwise have.

The problem is, I am very much a planner (which you can probably already tell) and he is more laid back. 99% of the time, I think that’s why we are so compatible, but I’m concerned he hasn’t realized the timing of everything. So far, I’ve only dropped hints by asking when he wants us to buy a house (“by spring of next year at the latest” he says) and he knows my thoughts on waiting until we are nearly married. I’m just not sure if he’s put A- B together to realize we would need to get engaged in the next 6-8 months. He’s not an idiot (has his Master’s in Physics), just not a planner like me. Even for my birthday or Valentine’s, he never plans anything ahead of time and realizes day of that he should do something. I’m normally 100% fine with that, I just will NOT be the one proposing so he’s on his own for this one.

Should I blatantly talk to him about the timeline of engagement and marriage? Would that make me seem desperate or crazy? I don’t want to because it ruins the romance of it all, but I don’t want this year to fly by and everything being delayed by a year because I didn’t say anything. I also don’t want to push him before he’s ready either, although he has told me several times he wants to marry me one day. Any thoughts? If you were the boyfriend, would you want this brought up, or does it ruin the fun/romance?

Thank you!

Comment: I’m with you on this one. I’m also a planner and yes, it can drive me a little batty with someone who isn’t. There’s some give and take, but when you like to plan things, you kinda just expect others to have an idea what planning consists of, and sometimes they don’t. I think in a situation like buying a house and getting engaged, that could end up being a problem. I would have a serious talk about it but not pushy about it. It’s a very slippery slope if you don’t word it correctly. I’ve never had that talk so it’s tough. Do it, just don’t be pushy about it.

Page 2 of 212


  1. vessel

    February 26, 2015 at 1:05 PM

    That email about clubbing and texting and winking emojis and what should I do? Etc. made me feel about one thousand years old.

  2. jay2

    February 26, 2015 at 1:30 PM

    First letter: My heart goes out to you as I can tell you have suffered a lot in your life. I, too, used relationships and friendships to fill the void I had/have inside, and that was always disappointing because very few people gave me as much as I gave them. I would say, stay out of Tinder as in many cities Tinder is just to hookup and I don’t think you are ready for random hookups. Why don’t you start getting your feet wet with other things instead? get into a club like Toastmasters (go to their webpage and you’ll be able to find a club in your city). usually you can meet friends there, lose fear of public speaking (which is linked to anxiety in social situations, you don’t even have to talk, just go to their meetings), the people there are really supportive and you can make friends. Or maybe look for a Landmark center in your area (google Landmark and see if they are in your city), during the time I went to Landmark I made very good friends who are still supportive of me until today. or if you have a hobbie (e.g. dancing salsa, going to museums) look for some Meetups in your area. Get some confidence back in yourself little by little, meet people with your same interests, and in time you’ll have a community. My doctor told me that the way to fill that void I had inside was to get a life of my own, get some hobbies and hang out with my girl-friends. Once you solve that area of your life you’ll be ready to date, otherwise you’ll be using that relationship to fill the void in you and it will leave you unsatisfied again. In terms of dating, my friends have had some average success with Match and the other “regular” dating websites. My prayers are with you. Keep us updated how things progress on your end!

  3. keddo

    February 26, 2015 at 4:04 PM

    First Letter Writer,
    I second what jay2 said. Another suggestion I have is to find a large (200 or more attenders) church in your area. Many churches have organized groups for people your age, and they will probably make an effort to welcome you and include you in their activities. If you try one church and they aren’t welcoming or their mix of people isn’t a fit for you, try another church. Like people, different congregations have different personalities.

    Woman living in Equador,
    You say, “When I try to start the conversation with him about all of this [money issues] he gets very upset and doesn’t want to discuss any further.” This doesn’t bode well for the relationship. I’m sure you’ve heard that one major key to a good relationship is communication. Communication is easy if you have chemistry together and are talking about delightful things. Any two intelligent people can pull this off. What is crucial for a long-term relationship is how you treat each other and communicate with each other when you are dealing with tough issues. Another major key to a good relationship is honesty. You have found out that he is slow to speak when the truth is difficult, and that he minimizes things that are/will be problems. Your problem isn’t that you are living in humble conditions, but that you are living with someone who isn’t forthright.

  4. jay2

    February 26, 2015 at 5:24 PM

    Second letter Confused in Miami — get out of that relationship ASAP, quit cold turkey, you are wasting precious time of your life, you are 30, if you want to have kids these are the years for you to meet someone to marry and start a family. That guy already lied to you by telling you he was separated, he is lying to his wife as well. He is not a keeper. Even if you two end up together how are you going to ever trust him? let’s just say this: if he wanted out of his marriage, he would have left already. He hasn’t left, so there you have your answer, he is never going to leave. As Steve would say, why buy the cow if he can get the milk for free: he gets to go home to his wife every night and have an emotional relationship with you on the side, he has the perfect situation, he doesn’t have to give you all his attention and deal in real life with you for limited hours of the day, that’s why it’s fun for him. You are the one who has to be alone at night and during holidays when he is with his wife. It’s not worth your time.
    It’s very interesting that you mention that you have never loved anyone like that, why is that? that’s a question that you have to answer — is it because he is unavailable and you have to make an effort? (women are hunters as well, we also like the chase) is it because he has certain characteristics that you find appealing (e.g education, physical attributes)? it’s worth for you to analyze why, why you love him in particular and didn’t love your previous relationships like that. Make a list, understand what’s going on with you. The better you understand why you love him, the easier it will be for you to get a new relationship with a single man that will float your boat the same way this guy does. Yes, you will have a heartbreak after breaking up with him but you will feel better. A year from now you will be glad you changed your situation.
    BTW if he does leave his wife, let him do it on his own, not because of you, because otherwise you will feel guilty and he will make you guilty later. Good luck!

  5. jay2

    February 26, 2015 at 5:27 PM

    Thanks Keddo! I agree with all what you said too! 🙂

  6. mrsjones

    February 26, 2015 at 7:17 PM

    Fyi, they say Tindr is for hooking up, but, both my sister and I both met our husbands that way. Yes, there are people on there to hook up, but that’s true of any online dating site. Many of the guys I met there (prior to meeting my husband), were in fact looking for relationships. 🙂

  7. rob22

    February 27, 2015 at 7:20 AM

    Ladies: a general rule about guys: If they are really into you, they will call / text several times a week (almost every day, except when they are truly very busy … and even then, they’ll make sure to touch base briefly to say hi) & will make plans to see you more than once a week (unless it’s long distance). They cannot stop thinking about you, wanting to talk with you & wanting to see you. It will be obvious.

    If they are interested in you to the point of wanting to hook up with you, and nothing more, then they’ll contact you when nothing else is going on & a hookup is convenient for them. In other words, they’ll contact you infrequently (that’s the clue). It’s not because they’re busy. It’s not because they are stressed about something. It’s not because they’re shy or introverted. It’s because, to them, you’re just a hook-up. Period. The fact that they’re nice to you before, during and after being on top of you is irrelevant. He may like you some, but not enough. But more likely he’s playing nice to make sure he’s still got that hookup option available next time.

    It’s not that complicated. Guys are simple creatures. If they are interested it is very obvious. If you have to question their interest, then they’re not that interested.

  8. enndea

    February 27, 2015 at 10:30 AM

    Dear Confused in Miami,

    You are me, 6 years ago. I met and fell in love with a married man. The circumstances aren’t important, but I can tell you it was an all encompassing, crazy, intense, passionate and emotionally draining relationship. He was always telling me that divorce was on the horizon. The wife knew about me and was fighting for the marriage. It consumed me. It ate up two years of my life. I loved him so much and just knew he loved me and “whhhyyyy wasn’t he with me??” One day I decided I just had enough. My life was passing me by and I was tired of not being enough and tired of waiting. I won’t lie. It was really hard. REALLY hard b/c he was begging me to come back, to listen, etc. But you know what? Within a year I had met an amazing man. The man I married and now have two sons with. He is incredible and the love we have is REAL and not based on fantasy. In the moment it feels like you will never love this hard again–but you will. And you’ll love better, and stronger, with someone who will love you in exactly the same way. You deserve that–we all do. Walk away. Do it today. And don’t look back. I can tell you when I do all I can think is “what did I even see in him??” Good luck to you.

  9. rob22

    February 27, 2015 at 1:09 PM

    In cases where the guy is married…. if he’s ALREADY separated & in the process of getting a divorce (and you can verify that) it’s legit. But I still question the wisdom of getting involved with a guy who’s going through a divorce. He’s going through a stressful time, may be on the rebound (some guys don’t do well without a woman), and may not be making rational decisions. But, at least he’s “possibly” not stringing you along. Keep in mind that this is still a poor choice for a long term relationship. He isn’t thinking straight and may reconsider his relationship with you after a few months, and possibly after you’re already married. Divorced once highly increases the liklihood of Divorced twice.

    If he has not truly initiated any divorce proceedings and is still in the house with his wife, see my post above. You’re a hookup to him. It’s not “because of his kids” or “because she will take him to the cleaners”. He’s just not interested enough in you to divorce his wife. You’re a hookup. Period. Any other explanation is honestly just an excuse.

  10. jay2

    February 27, 2015 at 2:04 PM

    Thanks MsJones! you are right, it’s true of any dating site.

  11. missannmcd

    February 27, 2015 at 6:21 PM

    Great insight and advice my peeps 🙂

  12. lsmith

    March 2, 2015 at 1:46 AM

    This is regards to the first email. I can only relate to this person because I am 36 yrs. old and I am a transfer student at a private unniversity. I am trying to get my BSN and I have 3-4 years to go. The Dean at my school highly recommended that I take a medical leave of absence that started last week which does protect my GPA. I am failing every class due to situatonal depression. My parents are getting divorced (mediation starts tomorrow) after 48 years together. They are both cancer survivors but the divorce was due to mental illness. My dad was diagnosed with delusional disorder and my mom is severely depressed, malnutritioned and is sedating herself with narcotics and controlled substances all day every day to avoid reality. Both of them were admitted to psych. facilities within the same year for help and once released both refused to continue treatment. So we are back at square one. I have consumed every day of my life trying to be there for them individually. I fell into a deep depression, started failing all of my classes. This is when I was offered this medical leave and free counseling until… my question to the original writer is what are you going to do in regards to finishing school? I DO agree with a lot of the opinions mentioned. I think the only website that is somewhat legit is EHarmony. Most of the other sites are free and is out for people to hook up. I am a strong believer in cognitive therapy and any sort of positive reinforcements like support or single groups. But you have to be happy and content alone before you can have a healthy relationship.
    STEVE… I am a huge fan of yours and of the Bachelor. Where I am torn as well is that I’m dating a guy I really like and feelings are mutual. He is exactly what I deserve and want in a man. I want to have a child in the near future but I should be back in school this fall. I don’t know if I should further my career and pray I get through and pass everything to become a RN, or do I just withdrawal from school, continue working as a medical assistant in big hopes that we will work out and we can have a family, just one child…which is a huge dream for me. I never expected my life to turn out like this. But he is an Engineer and reassured me, if we do continue in this wonderful relationship that he is actually ok with having a child with me even though he has two boys from his first marriage that he has full custody off. He also stated that we would be ok financially based solely on his income if we did get pregnant so I can be a stay at home mom. I’m afraid to wait until after school (another 3-4 years), getting into a large amount of student loan debt when I know I could and want to be a mom so bad. He is supportive of either decision. Any advice or words of wisdom.

    Thank you kindly,


  13. jay2

    March 2, 2015 at 7:54 AM

    Dear Lsmith,
    I recommend you to send your note directly to Steve to be included on this week’s Dr Reality Steve’s emails because Steve has mentioned several times that he doesn’t read the comments on his website, so you won’t get an answer from him here.
    As for your situation, here is my take, and bear in mind I don’t have the whole picture of your situation but here is what I think based on what you wrote:
    You are 36 years old and want to be a mom really badly, if you want your own kids, healthy kids, without going through very expensive fertility treatments, I would say start trying to have kids ASAP. For most couples it takes *at least* a year to conceive (for one of my friends it took her 3 years!) and then 9 months for the baby to be born so we are talking a couple of years from now (on average) by the time your baby is going to be born. Unless you want to adopt or go through IVF or other fertility treatments if you can’t get pregnant via “the normal way” because of your age. BTW IVF is very expensive and many of the procedures aren’t covered by some insurances in some states, there are deductibles, etc. so you have to keep all that in mind.
    Again, all of this is from the point of view of your wanting to be a mom. I know you aren’t married to the guy but if he is willing to do it, you love each other, go for it. Even if it doesn’t work out, you will be a mom and that’s the most amazing part. Plenty of my friends’ marriages didn’t work out but if you ask them, the one thing they don’t regret is having their kids. Yes, even if being a single mom is terribly difficult and challenging, they love being moms.
    As for your parents, I know it sounds awful but you have to stay out of that. You can’t control what they do. They have to deal with their problems and you can just be there for them but don’t allow this to affect you even further because you have enough on your plate (I know, easier said than done).
    As for school, I would go back and get it done otherwise you are never going to finish school and you are going to regret it. It’s not as if you are getting pregnant tomorrow (unless you are really lucky) so it makes sense to go back and complete your degree. Even if you get pregnant and have a baby, you can try to finish your degree -I had many friends at grad college who were moms so it’s possible to do it (not easy, but possible). Maybe Steve will have a different opinion, but this is what I would do. Good luck!

  14. jezziebezzie

    March 2, 2015 at 11:27 AM

    First letter writer? After I got divorced I realized all of my friends lived in a different town & I had nobody local to hang with since I had several years of trouble wrapped up in a 240lb baby! was a terrific way to find people in my area with my nerdy interests. And it’s at your pace. You can start with a group of all women doing something athletic & then once you’ve built up a little confidence you could try a mixed group that plays trivia or goes wine tasting or something that interests you. It’s not at all about dating, just about meeting people with common interests…but that’s a great way to meet someone. And if not, by then you’ll be much more comfortable with being out & about again and should be ready to try online dating (Tinder for the cool kids!) if you want to!

You must be logged in to post a comment Login

Leave a Reply

  © Copyright - All rights reserved

To Top

Privacy Preference Center

Close your account?

Your account will be closed and all data will be permanently deleted and cannot be recovered. Are you sure?