Dr. Reality Steve
I know you aren’t doing Dr. Steve emails right now but I have a guy question that is bugging me.
A little back story:
I met this guy 3 months ago through a mutual support group. I thought he was cute from the get go but didn’t want to rush anything. We saw each other everyday at meetings and it felt like he was flirting with me. We went out to eat, just the two of us a few times, and he paid. We would hug hello and goodbye. Then he text me one day and asked if I knew he wasn’t looking to date anyone. That got me nervous and paranoid, like am I being overly flirtatious? So it got awkward for a few days, but then we talked about it and everything was back to normal.
Back story on him: he’s been divorced 2 times and just got out of a 2 year relationship about 6 or 7 months ago. He doesn’t seem to have a lot of confidence in himself relationship wise.
Continuing on: We started going out to eat, the two of us or groups, and spending time with each other. He text me one night that he was sorry we couldn’t hang out because he ended up hanging out with some other people but next time it could be just us. But then he would act casual when we were face to face. We talked about not doing the friends with benefits thing, but did end up having sex twice now. The second time was the day after he hurt his knee which I thought was quite ambitious. That was 3 weeks ago. We haven’t talked about the sex thing since then. I took care of him for the week after he hurt his knee, getting food and stuff for him, going to see him and hang out, etc. Since then we hang out almost every day, and he texts me during the day asking how my day is going. He also thanked me for being such a good friend. And, last week I was having a rough day. He had text me earlier in the day (the “how’s the day going” text), and I told him what was going on. Then he text me that night to see how I was and I ended up going over to his house to talk to him about it. And, he has been cooking supper for us a lot too. He usually pays.
A friend of ours asked me one day what’s going on with us. She basically was asking if we are dating. I said no, we’re just friends. I told him what I told my friend, that we’re just good friends who hang out a lot.
So, my paranoid brain has some questions:
1. Is he sending me mixed signals? Like, does he like me but he’s not sure about how he feels? He’s told me before that he’s not sure where this will go, and he doesn’t know what he wants. He wants friends with benefits.
2. Did I make a bad move telling him about my conversation with our friend? I basically laughed it off while telling him because I didn’t want him to think I was still pining over him. Trying to act casual about it. I think it was fine that you told him that you told your friend what was going on. The fact he knows you told your friend “we’re just good friends who hang out a lot” and didn’t try and refute that or say “Is that all we are” to me tells me he’s happy with where things are. Not to mention, you probably shouldn’t be jumping into anything with a guy twice divorced and 6 months removed from an additional 2 year relationship.
3. This whole sex thing is bugging me. I feel like he’s second guessing having sex in the first place, but I don’t know how to ask him about it. If you want to see where you stand in the relationship you have to ask. If you don’t ask about the relationship, then the sex thing probably isn’t going to come up either. Either just continue on the way things are going now and give him more time since he seems to hint that he doesn’t want anything right now, or, bring it up and see how he reacts. Can’t get what you want without asking.
Hopefully I gave you enough information, but if not please feel free to reply with questions. I like this guy, but I don’t want to pressure him into a relationship. And, he’s told me before that he doesn’t want another relationship, but I feel like I’m getting signals that he likes me as more than a friend. Thoroughly confused.
Looking forward to any insight you might have.
Hi Dr. Steve,
So essentially I am in love in my colleague who is much older than me – I am in my late twenties and he’s in his late 40s. He is not married nor does he have kids. He is not my boss or immediate supervisor but we do work in the same department and sometimes closely together on tasks. Also, he works in our Boston office while I work out of NYC. Despite most of the above factors not being in my favor, it’s been about a year that I have had these feelings, and sometimes he sends signals that I believe may indicate they may be reciprocated. While he’s always kept it professional, we have numerous inside jokes together, are very chatty and jokey on the phone and via email, he’s never shy to compliment me or my work, he likes when I review his own work, and I know for a fact that he doesn’t speak to anyone else the way he speaks to me. Last week when he was sick with bronchitis, he emailed me just to apologize for not being chatty this week and that even speaking on the phone is physically exhausting (he did NOT have to do that). I know he would not have sent anyone else an email like that. Nor does he have inside jokes with others. Usually his emails to others are quite banal. Sometimes I push the buttons with him to get him to open up (full-court press let’s call it), sometimes he does and sometimes he doesn’t. Also, may I add that I am an attractive female. Anyways, while it’s impossible to know what’s going on in his head (for all I know this could all simply be admiration/respect for me as a colleague), it’s becoming an enormous strain for me not to say anything to him about it. I realize the risks involved, and the litany of reasons as to why I shouldn’t. I could even envision a situation where he responds with shock and concern, before politely telling me nothing can happen. However I’m not afraid of rejection, I just want to get it off my chest already. Perhaps his rejection would even allow me to manage my expectations enough for my feelings to dissipate. As long as my job does not get put in jeopardy, I’m okay with telling him. Based on all the above, do you think there is a chance feelings are reciprocated? Do you think it would be preposterous and moronic to tell him how I feel?
Comment: I can’t say one way or another exactly what he’s thinking or if I think the feelings will be reciprocated. I don’t know the guy. But one sentence stuck out to me that you wrote: “However, I’m not afraid of rejection…” Well then you should do it. Unless this will somehow jeopardize your career and/or your current job, if it’s bothering you that much, then say something.
With that said, my only concern is that he’s in his late 40’s, never been married, and has no kids. That screams to me someone that has no intention of doing either. Is that something you want to get involved in if he is accepting of your advances? What if he’s just horny old man that wants some arm candy? Be careful of that.
But if it doesn’t bother you if you’re rejected, then you might as well say something.
Long time no chat. I’ll try to make this quick, bc Lord knows I can write a novel:
I’ve been dating a guy for 4 months…his family loves me, and I love them. He’s head over heels and so am I. I made the mistake of telling him that I want complete honesty from him at all costs. I know he has issues with his filter, but I’m at a breaking point. He pointed out to me every single woman he ever had a thing for / hooked up with at work, church, wherever. Considering we go to the same church, I have to face these women – and it’s ALL of them (in our age group). I’m so uncomfortable being there because all I can see when I see them is the images of the past. I know you’re supposed to let go of the past, and he’s with me, therefore I shouldn’t be a pansy – but this is where it get’s worse: He keeps having dreams about these same women. And the dreams tend to be of sexual nature. He also describes them as if the women are coming after him and he’s trying to deny them. He says that he started having dreams bc we started fighting about these women. Then he told me that one in particular has been on his mind – on 2 separate occasions in the last 4-5 months we’ve been together. He also says that he’s bad at explaining stuff bc he makes it sound worse than it is.
I know he’s had a learning disability throughout his elementary/high school/college life, so I suppose it makes sense. But now his stories don’t even line up, and it’s stupid stuff. For ex, one night, when he was working, I was hanging out with our mutual friends and bc of a certain topic, it slipped out of my mouth that he liked every single woman in the church, and he exploded at me when I told him about it. Mind you, they were kind of on his side, telling me to let it go. I couldn’t understand why he was reacting the way he was, and then he told me he liked this black girl, who happens to be one of our mutual friends in the group. She’s dating somebody else and, quite frankly, I’ve never seen them talk or anything that would cause me to even be concerned. The contradiction is that when we first started dating and doing the small talk, he said that he generally isn’t into black girls but now all of a sudden, after I “hurt” him by saying that one comment, he decides that he liked this woman and that he generally DOES like black women. Look, whatever floats your boat, but the inconsistency of what he says is killing me. Especially since he told me he pointed everyone out, and now all of a sudden he forgets about this one. When we first started dating, he made the comment that if I were to ever cheat on him, he would forgive me. Now that I threatened to break up with him bc this girl keeps floating in his mind, he told me he would break up with me too if roles were reversed. A part of me thinks he’s insecure so he’s making stuff up to get me jealous. Another part of me thinks I’m the insecure one and I need to learn how to deal with it. The more this sh*t keeps happening, the less I want to be with him and, quite frankly, I don’t think I deserve that. I’m not one for horoscopes but even our “signs” say we will have a “short-lived” relationship. I just need a guy’s opinion. What do you think?
P.S. I’m writing only because you’ve convinced me with this: I’ve been voted the best relationship expert by a reality show blogger. Granted, I’m the only one who voted, but still. I’m here to help.
Comment: Well immediately, lets forget what signs you are. I think that stuff is garbage and anyone who puts any stock into whether or not they’re gonna be with someone based on how the sun and the moon line up is a bit looney.
I’m still a little confused actually as to why he’s telling you he’s having dreams about women that all hang out in your circles. What’s the point of that? Seems a bit immature to do that. And not only just casually telling you he had dreams about them, but going into sexual detail? This guy is a moron.
The fact he told you he would forgive you if you ever cheated on him is a red flag. That doesn’t make sense to me. Maybe he could say he’d forgive you, but your relationship would never be the same.
This guy is kind of a head case. Seems to be a little too much drama in his life and seems like a horrible communicator. Not because of anything astrological, but I don’t see it lasting long between you two. This is all just weird.
Send all links and emails to: firstname.lastname@example.org. To follow me on Twitter, it’s: www.twitter.com/RealitySteve. Instagram name is “RealitySteve,” or join my Reality Steve Facebook Fan Page. Talk to you tonight.