How Do I Know When the Relationship’s Worth Fighting For?

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Call Your Boyfriend

Hey guys,

After today’s column, Call Your Boyfriend will be going on hiatus. I’m moving to Los Angeles very soon so I can have lunch for four hours without anybody judging me, and so I can get a dog and a boyfriend. (Oh, you didn’t know? I’m single, which means that one day Call Your Boyfriend could actually become a reality for you! Holler. No, seriously. Holler. Dating in L.A. sounds as exciting as a root canal and I’ll need all the help I can get.) In my absence, you can still always email me your questions. I’ll miss you guys. Stay beautiful, and if I’ve taught you anything at all with these columns, always be honest about your feelings. It’s too painful not to. Smooch!

I’ve recently just come out of an on-again off-again relationship with an incredible woman. The one major issue that we had was that she had two kids, and I knew that it was a responsibility that I simply wasn’t ready to take it up. There’s a gap in age (I’m 32, she’s 37,) and I still feel relatively new to dating (I first started when I was 26.) I still feel like I need to date around, see more of the world, and sort of work harder to bring about my own personal goals before I’m ready to settle. Here’s my question: do you think that maybe in a few years, I can find a way back to her? She’s really an amazing person, so I would greatly appreciate your advice.


People always say things like, “if it’s meant to be, you guys will find each other again….” And you usually want to tell them to please stop talking like Lauren Conrad on a very dramatic episode of “The Hills.” Still, there is truth to it. I think a lot of a relationship’s success is dependent on timing. Right place, right time, right wants and needs. It’s completely possible to meet someone and be like, “OMG, if only we were in the same place in our lives, we could truly build a life together.”

So here’s the deal: I think you’re very brave and smart to walk away from this relationship. It’s not easy to break up just because you know the timing isn’t right. You could’ve easily faked it and been like, “You have two kids? Fantastic. I am so ready to take on that challenge!” But you were mature and did the right thing. Now you can use this time to sow your wild oats and essentially discover who you are and what you want. If, when you’re done with this whole self-discovery process, she’s still there and it makes sense for the two of you to get back together, fantastic! If not, take solace in knowing that you got to experience an amazing love, because many people in this life don’t even get that. Love will find you again. As you said, your journey is just beginning. (Okay, now I sound like Lauren Conrad again. Sorry.)


So my story with this guy has been going on for about 6 years. I know that’s a long time, but we’ve been best friends for that long. And I’ve always had a thing for him and he knows, but at first he just wanted to be friends. As years went on we got closer. So to make a long story short, I’m the only girl in his life but some of his friends don’t approve of me. We hung out in public some before he started hanging with this one guy who rules his life. This year we went over the friendship line and the chemistry for me was AMAZING! He’s the type to fuck a girl and leave, but with me he hasn’t. He’s just not ready to be my BF. When he didn’t want anyone knowing about us, it was killing me, but people could tell we were together just by seeing us talk in school. Please help me!


Confused Cinderella

Hi Cinderella-ella-ella-ay,

You should NEVER be with someone who wants to keep you a secret. Enroll in “How To Love Yourself” at your local community college and you’ll see why. This guy sounds like a coward and possibly gay. Chew him out for being a dick, and then move on to another dick who’s not ashamed to be seen with you in public, okay?


Hey Ryan,

So I’m a huge fan and would love if you would answer my letter, but it’s not going to be the easiest to sort through. 

I’m writing to you because recently, I have come to the realization that I have approximately zero fucks to give when it comes to my boyfriend. We’ve been dating for close to a year now, and our issues are as follows:

1) He refuses to go out and socialize within a group context. He’s declined numerous times to meet different groups of my friends, and as of now, has only met three of my friends (two from college who live in a different city, and one from our city). He basically only likes to go out with the two of us, which frankly gets a little boring sometimes.

2) This problem is somewhat unique to gay relationships, but for three months I have been politely asking him to let us change up our sexual roles for one night, if you catch my drift. He’s done it before, so it’s not like he’s completely averse to it, but he keeps pushing it off and not making it happen even though I’ve said it’s important to me, so resentment is starting to build on my end.

3) We both recently started new jobs with different schedules. He’s working long, traditional hours (60+ hours per week) and I’m working a standard 40-hour week but in the evenings. By the time I get off of work, he’s asleep. It’s made spending time together really difficult, and basically has been the icing on the cake, forcing me to finally confront my relationship frustrations.

So basically I’m asking for a type of framework to evaluate my relationship. Some way, besides maybe a traditional pros and cons list to help decide whether it’s time for a break, to end it all together, or to stay together and just work on the issues.

Hey boo,

It’s always hard when I get these types of questions because my first instinct is always to be like, “OMG, yeah babe. Your relationship sounds terrible! You should dump him!” Then I realize that I’ve never met either of you and to dole out such flippant advice on such a major issue would be irresponsible of me. All I can do is deal with the information I’m given and provide a measured response, right? Okay, here we go.

Not to be too crass but if your partner is not open to switching things up and won’t screw you the way you like to be screwed, he needs to GTFO!

Usually when deciding to end a relationship, you need to be 100% real about your feelings and ask yourself, “How much work is this emotional shitshow worth?” Because some relationships are worth the shitshow. They are worth the top/bottom dilemma and the different work schedules. You just have to be honest and be like, “How much do I want to fight for this? Does the ecstasy outweigh the agony? Also, do I ever see things really getting easier?” How you answer those questions is usually an accurate indicator of what you should do.

As a gay man, the problem that seemed the most serious to me was actually the issue of sexual positions. Not to be crass, but regardless of sexual orientation, if your partner is not open to switching things up and won’t screw you the way you like to be screwed, he needs to GTFO! Also, the fact that he won’t socialize with your friends is annoying. I always respect a couple that is able to mix in friend groups without seeming like they’re in their own couple-y world. That to me shows maturity. Like, wow you can be in love, and be a functional member of society? Awesome!

Oops, this answer isn’t so measured anymore, is it? Whatever. Just remember that you only have one go-around in life, so you better make it good. You better be having amazing sex and hanging with your friends and be spending your time with someone who makes everything brighter in color. Otherwise, you’re just spending your precious time collecting regrets.