Dealbreakers: How Judgmental Should You Really Be?

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Ryan O’Connell is a New York-based writer. He likes shoegaze, the Olsen Twins, and figuring out why people do the things they do. Oh, and he tweets. Check back each Thursday for his latest Call Your Boyfriend column.

Hey boyfriend,

So I’ve been seeing someone very casually for the last two months. He’s really great, we get along so well, but…. This is going to sound kind of superficial but he has TERRIBLE style, to the point where it’s almost embarrassing to be seen with him in public.  Plus, he’s horrible at texting. He takes forever to text back and when he does, his messages are rife with spelling and grammatical errors. Are these legitimate dealbreakers or am I just being too judgmental?


Hey Judge Judy,

Ughhhhh. Dealbreakers. I hate that word because it seems like EVERYTHING is a dealbreaker these days. “He blinks too much! Dealbreaker. He likes Dave Matthews Band! Dealbreaker!” When did we turn into such assholes? We complain about the dating game being too hard and having these unfair high standards be put on us but then we go ahead and also enforce those very rules we claim to abhor. It’s hypocritical, not to mention it’s probably keeping us from the one thing we want, which is a relationship.

Do you know who my mom has been dating for the last decade? A total country bumpkin’ who likes to hunt and have an occasional taxidermist moment, which is the opposite of who she is. She told me that when she first saw him, it was like, “Dealbreaker, dealbreaker, dealbreaker!” until, you know, she finally got to know him and was like, “JK, I’m obsessed.” My point is to not judge a date by its profile picture. I used to think that if a dude was into The Smiths and liked Christopher Guest films, it’d be enough to sustain a love connection between us. I completely focused on the superficial and then became surprised when a shared love of emo music from the ‘80s wasn’t enough to keep things interesting.

At this point, I will date someone who looks like Danny DeVito, so long as he’s hilarious and kind.

Of course, there are legitimate dealbreakers. I think the three things you have to see eye to eye on are sex, politics, and religion. If someone has a different value system than you, then yes that is a real concern. But something like personal style? Forget about it! That’s such a non-issue! You can always teach someone how to dress better. You can’t, however, teach someone how to be a decent person.

I remember when my BFF started dating someone who was, for lack of a better term, not chic. I was very bratty about it and didn’t understand what she saw in him. Then, as I got to know the guy and their relationship better, I realized he was an amazing man who also happened to be OBSESSED with my best friend. We all should be so lucky, right? At this point, I will date someone who looks like Danny DeVito, so long as he’s hilarious and kind. As you get older, you really start to understand that the other stuff just doesn’t matter as much. I think people who are still like, “He wears ugly shoes and he’s an inch shorter than my ideal height” are just looking for excuses not to be with someone. A person who has a lot of dealbreakers reads to me as someone with intimacy issues. They’re just looking for reasons to not commit.

That being said, I am guilty of judging. We all are. I once went on a date with someone who sipped his wine THROUGH A STRAW and the first thing I did (after making out with him — what can I say, he was cute) was run home to my roommate and be like, “Oh my god, isn’t it crazy that he does that, that he just sips his wine through a straw? I can’t be with someone like that, he’s clearly mentally ill!” As it happens, the guy did end up being kind of a weirdo, but it had nothing to do with how he liked to consume his wine. Looking back, I know that I was just looking for any excuse not to go on a second date with him. Because doing that would mean I’d potentially like him and then we’d maybe date and fall in love and he’d break my heart! I liked it better over here in Netflix-and-fifty-cats-land. It’s safer!

We should all work on being more open-minded rather than looking for opportunities to push away love. Dating someone who dresses poorly and abbreviates in texts should be the least of your concerns because that stuff doesn’t mean anything. It’s not who he really is! Ask yourself, fashion issues aside, if this dude makes you happy and seems to get you. If the answer is yes, then I’d hold on to him for dear life. It’s rare that you find someone like that. You don’t think it’ll be that rare in the beginning of your dating life, so you take people for granted. But the truth is that truly connecting with someone is special and hard to find. So don’t throw it away over some Chinos, k?


I’ve been out four times with this guy. We get on very well, have great engaging conversations. But the thing is, he hasn’t initiated any significant physical contact. There’s been some very chaste kissing and hand holding but nothing else. (Did I mention we’re both almost 30?)

All our dates have been in public so far, so not really conducive to full-on making out. On our last date, I walked us to a secluded section of a bookstore hoping he’d at least attempt to shove his tongue down my mouth, but nothing. I kissed him, but he didn’t take it any further than that. I’ve tried nonchalantly asking him about his dating history, and I suspect he’s inexperienced. Partly I wonder if he’s just shy, but part of me also wonders if in fact he’s just not into women but hasn’t realized or accepted it yet.

I feel like I haven’t known him long enough to broach this…but what’s a diplomatic way to figure this out, short of asking him if he would like to be on me (to quote Anchorman)?


Questioning if my date is questioning

Hey babe,

Ah, welcome to the perils of modern dating! A time when a man is assumed gay until he’s literally eating out your vagina and even then you’re like, “Hmm, IDK. Maybe he’s just not that into girls.”

To a certain extent, I get your paranoia. I have been with many a “straight man” in my day (one of whom is married now, which is so #dark) but at the same time, may I suggest you take a Xanax in the bathtub and chill for a sec? Just because a dude hasn’t made out with you yet doesn’t mean he wants a P in his A.

It doesn’t matter if he’s straight or gay at that point. If a dude is still giving you coldness after you’ve gone out of your way to make the first move, you need to get out of there.

From what it sounds like, he may indeed be shy and inexperienced. As you mentioned, all of your dates have been out in the open and you know what? Some people just don’t like PDA. The other day I was telling my friend about my propensity for making out with dudes in public (I know, I’m THAT guy, I’m sorry!) and my friend was like, “I’ve never made out with someone in a bar or in public, ever.” Now keep in mind that this is someone who has been in a long-term relationship before and dated a bunch. When he told me that, it dawned on me that some people are not into the whole world seeing their make out face. That doesn’t make them gay. It just makes them more reserved (and have more self-respect and dignity than someone like me).

You said that the only time you’ve made a move on him was in a secluded part of a bookstore and that he didn’t respond to it well? Well, that’s not entirely surprising. Beating up someone’s tongue in the Self Help section would even give a ~~~free spirit~~~ like me pause. In order to really know what the deal is with this guy, you need to have a one-on-one date in private. Invite him over to your house to watch a movie or eat dinner and if he’s still like, “OMG, get away from me, AHHHH!!!” we’ve got a problem. It doesn’t matter if he’s straight or gay at that point. If a dude is still giving you coldness after you’ve gone out of your way to make the first move, you need to get out of there. Life is too short to waste on someone who’s not gung ho about jumping your bones at every opportunity. Everyone deserves to be with someone who makes them feel hot and sexy. That’s a partner’s damn job: to make you feel like a million bucks even when your account is overdrawn. If you’re walking away from each date feeling like humpty dumpty, it’s not worth it.

No matter what you do, though, don’t confront him about his sexuality please!  If he’s actually straight, you’re going to give him a complex. And if he’s gay, you might scare him further into the closet. People used to ask me if I was gay before I came out, and it made me want to scream bloody murder and burn all of my Billie Holiday records. The more important issue is whether he wants to bang you, often, perhaps for a very long time.