Help! My Friend With Benefits Wants To End Things: Ask A Pro

By The Head Pro

Dear Head Pro,

About two months ago this bro and I started hooking up. I have never been the relationship type, but about a week in I could tell he started getting serious with me than I preferred, so I sat him down and let him know I wasn't interested in anything serious and it would be better if we had a friends with benefits type of situation. He agreed, and all was well for a long time. We would hang out, go out, smoke together, etc.

This past Saturday while we were out together and a few of our friends, I stupidly and drunkenly made out with someone else, thinking he wasn't around to see. Turns out he was right behind me (oops). He got all pissed, rightfully so I guess, and stormed off. I went after him and we started to have a drunken heart to heart, but both decided it's better if we talked the next day in person in sober.

So I texted him the next day saying sorry for being an asshole last night, and he responded with, "I blacked out at the bar. How were you an asshole?" I thought I was catching a lucky break and told him I was just being a bitch to him for no reason, and he responded with "it's all good".

The next day he texted me to meet up, so we did and that's when shit got real. He basically sat me down and was saying how he doesn't want to be friends with benefits because he was getting emotionally attached and that when he would see me talk/flirt with other guys he got jealous and that wasn't fair to me. I understood where he was coming from, up until he kept trying to turn it around on me saying that he doesn't want to hurt me and he's afraid he will. WTF? I've never given him any interpretation that I was attached in any way, and told him he didn't have to worry about me, and then he would turn it back to himself and say he didn't want to get hurt.

So what's his deal? Do you think he really is doing this because he's afraid of getting attached and just trying to blame it on him being afraid to hurt me, or do you think that he just isn't into it anymore and thinks that I'm the one that's getting too attached?

Is it him or me?

Dear It’s Mostly You,

Ugh this is why “arranged” FWB situations are a dumb idea - they never work. People fall into them, maybe, but setting one up is about as sexy and effective as using a shower cap as a condom. What’s even dumber is that your question isn’t about why it’s not working - it’s about his explanation for why it’s not working, as if that even fucking matters (it doesn’t).

People in your situation do exactly what you did all the time: One person develops feelings, and so the other says “look, I’m not feeling that, but we can keep fucking as long as you know that’s all it’ll ever be.” They do this to clear their conscience, which is bullshit - what do you expect the person to say in that situation? They express their feelings for you, you break them down by telling them “thanks but no thanks,” and then offer them one last thread to dangle from. That’s shitty. Pro tip for everyone reading this, the minute your fuck buddy expresses feelings, get out, or else it will end like this.

As for why he’s saying what he is re: not hurting you? It’s all male posturing and bravado. He’s reciting the narrative even though it doesn’t apply here, because that’s normally how things go. Basically, he’s hurt and trying to save face in the lamest way possible. Of course he should have distanced himself a lot sooner, but people do stupid shit when they like someone.

Detached Kisses,

Head Pro

Dear Head Pro,

Long story short I've known this guy for all of high school and now were in second year at different colleges. He liked me for most of high school and I was never sure how I felt but in the last couple years we've hooked up a few times. We've talked numerous times about what our relationship is and never really come to a conclusion. Thing is, I can't stop thinking about him. He's said he wants to keep hooking up but isn't looking to date, but I don't think friends with benefits will work if we both have stronger feelings for each other than just friendship. Is it time to move on? What do I do?


To FWB or to not FWB

Dear FWB,

I think I know a girl who would be perfect for him. See previous email.


Head Pro

Dear Head Pro,

The summer before I entered my senior year of college, a yacht-sinking bomb was dropped on me.  The gravy train was nearing it's end. Even daddy-dearest said a job would be a good idea to "solidify my resume."

That being the case, I scrambled to find a job. Waitressing/hosting/retail was obviously out of the question, so in May I settled on an intern position at a law firm. After an interesting adjustment period, in September I was asked to stay on for the school year. Money is pretty good, but it sometimes isn't enough. And by sometimes, I mean all the time. I'm constantly having to choose between going out or shopping.

I'm all about working smarter, not harder. Before I jump ship and find another job, how do I ask for a raise?

Kisses from the clearance rack,
Newly Broke Betch

Dear Newly Broke Betch,

Well, the first thing to do would be to drop the bullshit affected tone of your email, which at this point no writing for this site has sounded like since, I dunno, 2012 or so. Secondly, don’t sneeze at waiting tables or bartending. Yeah, you have to give up some prime party hours, but those girls make bank. Just sayin’.

Anyhow, you have to first find out if a raise is even available - for an intern, lots of places pay a set hourly wage. If there’s wiggle room, the next and most important step is to be able to justify your request. That is, what concrete examples of work can you point to that demonstrate you’re taking on more work than you were when you started? More importantly, what proves that you’re capable of taking on more work? Are there projects or assignments you can highlight that show where you learned a new skill, or at least mastered one that’s difficult for newbies? Do you have in mind ideas for work you can take on to justify the increase?

If you can do that, it’s pretty easy to go to your boss and say “When you brought me on at $9/hour, I was just learning the basics. Now I help so and so with x,y, and z tasks that I believe make me a more valuable intern, which is why I’d like to talk about increasing my pay to $11/hour.” While normally in a negotiation you’d want to shoot for the moon, in your case stay realistic - three, four dollars more per hour TOPS. As an intern, you’re just too replaceable for them to tolerate having someone on the floor who thinks they ought to be making $20/hour. If you want that kind of money, be a waitress.

Otherwise, just be pleasant and confident. Don’t let them bully you away from having the conversation in the first place. Pick a time when your boss doesn’t want to kill himself (probably never, since this is a law firm), and go in there and deliver an articulate, well-thought-out argument.

Yacht-Sinking Kisses,

Head Pro




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