My Boyfriend Of 4 Years Hasn’t Said ‘I Love You’ So Should I Say It First? Ask a Pro

Dead Head Pro,

So about a year and a half ago I cheated on my then boyfriend drunkenly with one of his friends (yeah I’m a bitch). And he obviously got pissed and has openly hated me (along with all rest of his friends) it was ugly. Anyway, We graduate and then in August he starts drunkenly sending me all these texts yelling at me about how I cheated .. Very annoying and it happened so long ago, like get over it. Now I can go a little BSCB when I black out so then one night, a few weeks ago, I see him out and we got into a heated argument about the matter and then for some reason tell him I still want to have sex with him (he’s great in bed). So he decides to finally forgive me and we start sleeping together again. Now I want to make this guy my boyfriend again but I don’t know how to approach him cause the breakup was clearly my fault. He hasn’t mentioned anything about the matter nor has he told any of his friends (because of the cheating obvi) but do you think we have any chance of getting back together or is he just blatantly using me for sex?


Cheating Whore

Dear Cheating Whore,

Yeesh. I don’t think, necessarily, that it’s an either/or kind of thing. I doubt he’s outright just using you for sex (though possible, I guess), nor do I think that he’s trying to embark on the path to a renewed relationship. Odds are, this guy is probably dealing with a lot of conflicting emotions. On the one hand, he undoubtedly felt incredibly emasculated when you cheated on him, and getting back into a sexual relationship with you is one way of mitigating those feelings (making him feel “manly” because he got back with you). On the other, his intellectual side is telling him that what you did makes you awfully untrustworthy, at least for the foreseeable future.

If you want this to go anywhere, unfortunately you’re going to have to have a very serious conversation about where he’s at, where you’re at and what both of your intentions are. Personally, I would be hesitant to get back with the psycho who started a fight with me over an ancient breakup, just as I assume you would be hesitant to become involved with the broken manchild who wouldn’t stop harassing you a year+ after he dumped you. I would say you need to stay the fuck away from each other, but if that’s not satisfactory you need to put on your big-girl pants and have a talk.

Cheating Kisses,

Head Pro

Dear Head Pro,

A couple of months ago I was at a frat party and bumped into a guy I know. He was trying to dance with me and at first I wasn’t very into it. This keeps happening for a while and he’s being very persistent. After a while though I decided, fuck it, and we starting hooking up. Mid-way through making out, he suddenly tells me he has to go to the bathroom and that he’ll be right back and leaves. I decide that there’s no way I’m going to wait for him alone at a party, since all my friends left after we started kissing, so I leave without waiting for him.

Fast forward to two nights ago, when the same guy texts me completely out of the blue. I’m completely surprised, since he’s a pretty shy guy and clearly inexperienced with girls. Also, we hadn’t talked, or even seen each other since the first time we hooked up. He asks me what my plans are that night/if I want to hang out/etc. I make it clear that I’m staying in to watch a movie and chill out with friends. Despite this, he keeps texting me and after about an hour of conversation I finally give in and invite him to my room, although I make it clear I’m not promising anything. He shows up and we start cuddling, and eventually hook up again. Just when things are starting to heat up though, he says something along the lines of “It’s late, I should go” (keep in mind this is 1:30 on a Friday night). He leaves.

I’m so confused. Twice he’s initiated and pursued, and twice he’s bailed half way through. I don’t understand what he wants. I totally get it if he just wants to hook up, because I’m honestly not looking for anything serious either (and have never hinted to him that I am).  If that’s the case – why wouldn’t he stay for sex?  I just don’t know why he would booty-call me and then leave me high and dry when I am clearly DTF.



Dear Confused,

Well, for starters there’s the fact that his initial advances were spurned because you weren’t all that into it. Guys remember that, especially shy ones who more often than not go into interactions with women expecting to get rejected. If he really is that shy and inexperienced, it’s pretty reasonable to assume that he has some trepidation crossing the line from just fooling around to butt stuff. For all you know, by-God coitus may even be uncharted territory for him.

There’s also the possibility that he sees himself as an “old fashioned” kind of guy and is trying to follow some kind of protocol (however misguided) that says it’s improper to have hot sweaty sex with a young lady the first few times you leave your calling card in her foyer or whatever the fuck. Considering that he was “very persistent” after being refused something as simple as a dance, it’s not unrealistic to think that he’s manufactured some real feelings for you and wants to work his way into an actual relationship. Also, don’t be so sure you were “clearly DTF” – you appended your invitation with a warning that you weren’t promising anything.

Either way it’s kind of weird, and either way I don’t think you’re going to find the sort of NSA, casual thing you’re looking for. For all you know, by the time he’s worked up the nerve to get his dick wet, he’s already gone ring shopping. If all you want is a guy you find amenable who will fuck you without many questions asked, I think a college campus is a pretty ok place to look for that.

Or maybe he’s just gay,

Head Pro

Hiya Head Pro,

Getting right down to it, I have been dating my boyfriend for over nearly four years and we have yet to say “I love you.” Do I love him? Yes, more than I’ve ever loved anyone. Do I know he loves me? Yep. A) We’ve been together almost four years… if you don’t love your partner after that long then you are probably a robot. And B) his actions never make me question his feelings. So in actuality, there is no real problem here since I have a happy relationship, but damnit! I want to hear the words!!!

A part of me thinks he hasn’t told me he loves me because it is so grossly overdue that by now that it would be kind of awkward. Like ‘yeah, no shit you love me, thanks.’ Yes, I could just be the one to drop the L-word first, and most of my friends have encouraged me to say hell with it and do just that, but I believe most men (and yes he’s a 31 year old man) know that it is their responsibility to be the first to say it, so I’ve continued to wait and hold my ground. At this point I feel like we are going to get married one day and have the world’s most awkward vows. 

So obviously I can’t make him say anything nor can I put words in his mouth, but maybe there is something I can do that I haven’t thought of?  Short of just giving in and saying the words first, what do you think?

Domo arigato, xoxox

Miss Roboto

Dear Miss Roboto,

Ha, this one made me laugh. Those would be awkward vows indeed! I think you nailed it, at this point it would be so weird and obvious that it’s overdue that he’s not sure of how to go about it. It’s kind of like when you get an email or text from a 2nd-tier family member, and you’re like “aw fuck, what do I even have to say to aunt Mildred? I’ll reply to it later.” And then like three weeks pass and you never do, and by then it’s way too late and doing so would only make obvious how long you waited. All relatives should be banned from using Facebook, email and cell phones.

I agree that it’s strange and needs to happen, and while at this point it’s getting a little petty (are you REALLY going to hold out on saying it after four years?), I guess I understand. How about, the next time the two of you are having a good time splitting a bottle of wine or four, why not (pleasantly, playfully) say something like “You know, I don’t think I’ve ever told you I love you. Come to think of it, I don’t think you have either. How crazy is that!?!?!?”

You just have to get the first one out of the way. Hopefully, he gets kind of bashful/sheepish about it and says “well I can’t believe that, I love you so damn much” and then takes you in his arms and dips you for a kiss and then you two have all of the sex and babies. If he says something like “that’s fine with me, I don’t believe in labels,” that’s stupid and shitty and you should probably break up with him.

Belated Kisses,

Head Pro

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