The One Thing You Get Wrong About Telling Him How You Feel: Ask A Pro

By The Head Pro | October 17, 2017
Mascot

Share this sh*t

Head Pro offers advice on life, love and really anything because he likes to hear himself talk. Email him at [email protected], and follow him on Twitter and Insta at @betchesheadpro.

Here’s my current dilemma that’s consuming my thoughts:

Summer before my freshman year of college when I was 18, I met a guy. Fast forward a couple months, I’m thinking I pretty much found my soulmate. He is one of the funniest, loving, sweetest guys I’ve ever met. He is the epitome of Jim from The Office, which, let’s face it, is every girl’s dream guy. I wanted to date, he didn’t because we were “too far”, aka 1-2 hours away depending on when he was away at school. Whatever, K, I got over it. I started hooking up with guys at school cause that’s what freshman do, and then we started talking again, but only hooking up and just hanging out. Over the next year, we were just fuck buddies while I did my thing and he did is, even though I still had feelings for him. My junior year, we started hanging out more, going out more, hooking up more. And the sex is really fucking good.

I’m now a senior and 21 years old. I’m over every guy that goes to my school (no, not under) but I just have never met another guy like him before. I can honestly say he’s my best friend, he’s been there through everything I have gone through in college, including the death of my father, and I love this guy. I know feels the same about me and tells me he loves me and we act like a couple when were together, and we are still banging to this day, literally, but he hasn’t shown any interest in dating. I’ve known him for almost 4 years now, and now that we are both graduated/graduating college I want to be with him. I have no idea how he feels because he’ll text me a lot for a few days or not at all for a few days. He even wants me to go out of state with him in December, go to a concert, stay in a hotel, and enjoy the weekend. So, he’s planning couple things with me in December. Like WAT. Meanwhile, I know he doesn’t talk to any other girls or hook up with anyone else because he straight up tells me this and I can clearly see it while I’m looking over his shoulder at his phone (whoops).

My friends say to tell him how I feel, but I’m scared because it didn’t work out well the last time. I know he has no one else, so what is he waiting for or do you think these feelings are one-sided?

HALP

Let’s get one thing straight, Jim from The Office should be no girl’s dream guy. Jim’s ability to land Pam rested solely on him being the one non-weirdo in that office. Otherwise, he fucked around for like a decade, had no real ambitions and kind of treated Pam (and later, their daughter) as a burdensome accessory in his life. Fuck, at least Roy was ready to kick some ass. She would have been no worse off with him, I think. Don’t @ me.

Anyway, just fucking tell him. It’s reasonable, given that you’re graduating soon and have some important decisions to make. It’s also pretty weird for him to drop “I love yous” and shit without ever even once mentioning the status. It’s in a sense a silly thing (after all, sentiment is most important), but it still matters.

But more importantly (and I probably bring this up in our book): if a guy’s going to refuse to commit to labeling a relationship, it won’t be because you asked the question. Like, that’s insane. How does that even work, you tell him how you feel and he responds “hmm, despite all of my behavior that would indicate I feel the same way, now that you’ve brought it up my feelings have diminished?” It doesn’t happen, and has never happened. The last time it didn’t work out was because he had a pretty legitimate reason for not wanting to commit, not because you bothered to ask.

FWIW, almost no one I know is still with the person they were dating in college (I am le old). With someone they met in college at some point? Sure. But if you pour your heart out and this guy’s still wishy washy about being serious, you might have to start taking evasive measures. It’s what Pam should have done.

Jim The Office

Dear Head Pro,

I am experiencing an uncomfortable level of confusion in my relationship with a guy that I’m interested in and need your guidance.  Here’s the annoyingly convoluted background:

Had a one night stand w this guy I know and when I didn’t hear from him the rest of the weekend I wasn’t shocked.  Come Monday, it turns out he had tried various forms of social media to get in touch with me, I just didn’t realize, so we began chatting.

He asks me out to drinks and he decides to make drinks a dinner, which I took as a good sign.  The date went really well and was a lot of fun but at the end he got very awkward, gave me a weird side hug and essentially ran away (I expected a kiss considering we had already had sex…). I left the date very confused but pretty accepting of the fact that clearly he wasn’t into it. Didn’t really hear from him until several few weeks later when he suggests we do it again and instead I invited him to meet my friends and I out at a bar that night,  He comes, we have a lot of fun and I go home with him again.

Jump even more weeks of minimal contact and we make a plan to go to the hang in a public setting but when I drop him off he gives me another awkward goodbye, a shoulder squeeze.  The next week he invited me to this party from which we leave together again, but I don’t have sex with him and don’t really explain why (we did other things though so I feel like it was fine). In the morning he makes me breakfast but doesn’t kiss me goodbye.

Then he goes several MORE weeks without really reaching out to me!

By this point I was fed up with the inconsistency. As a large group we went out to a bar where I accidentally blacked out and maybe slapped him and called him an asshole; but apparently he didn’t mind too much because I woke up in his apartment.  He said we were cool, texted a little the next morning and all seemed fine. Once again, weeks go by, he has texted me a few random times and IMs me but never keeps the convo going very long and never suggests hanging out.

So bottom line: This guy has been very hot and cold and hasn’t asked me on a real date in two months but will still sometimes reach out but not to hangout or hookup so like wtf is the agenda.  I was under the impression that if a guy is into you he will ask you out or text you frequently.  On the assumption that he is just too awkward to function, should I keep making an ass of myself by putting myself out there and straight up ask if hes interested (which I may have done that blackout night and don’t remember, i.e. may have already been denied-Yikes), or do I gather my remaining dignity and move on?

Sincerely,
Feeling too old for the hot and cold

Eh, I don’t think this is all that complicated or inconsistent. Take the one-nighter out of the equation, and you’re describing a brief relationship that never got off the ground between two people who never liked each other that much. Let’s break down these encounters:

– One Night Stand: Presumably booze-fueled. No explanation needed.

– First “Date:” He’s probably feeling a little awkward about how things started and wants to reset a little bit. Has a nice time, wants to feel things out on a romantic (as opposed to purely sexual) level. I can probably count on one hand the times I’ve tried to kiss someone on a first date, and I’m not exactly Mike Pence. Just doesn’t always seem right.

– Second “Date:” I think you kinda fucked up a little here, given that he wanted to meet one on one and you did the “let’s make it a group thing” thing. Then again, it’s understandable given that he’d been radio silent for a while—no blame to go around, really, just poor communication. You meet up, the booze and social energy is flowing, and you smash. Cool.

– Third “Date:” You hang out in public, (presumably) sober. Still has a nice time, I guess? Another awkward goodbye.

– Fourth “Date:” Hey look at that, another party! And wouldn’t you know it, you wind up going home and doing sex stuff again. I’m beginning to see a pattern here…

– Final Encounter: It doesn’t sound like anyone actually invited anyone out here, you just ended up there as part of the same amorphous friend group. And wouldn’t you know it, a lot of alcohol is involved again. And you wind up fucking, again. Color me surprised!

So yeah, besides his sporadic communication he’s not really inconsistent. Other than when drinking lowers both of your inhibitions and you wind up touching each other in some places, it doesn’t sound like he likes you all that much—and to be fair, it doesn’t sound like you were walking on clouds after your dates, either. I think he was pretty obviously struggling to feel the vibe after the first few go-rounds, and then after whatever transpired at the bar he knew that this wasn’t something worth pursuing.

He’s still gonna hit it, though, because why not? That’s life. Consider not going on dates with men who only contact you once per menstrual cycle and that you don’t seem to like that much either, and you will be much better off.

Head Pro offers advice on life, love and really anything because he likes to hear himself talk. Email him at [email protected], and follow him on twitter and insta at @betchesheadpro.