Why Am I So Indecisive About Dating?


Hello, Doc.

I’m a long time reader (male, straight) who has been following your site on and off since high school; currently, I am in my mid 20s, with no dating or sexual experience. This doesn’t bother me, per se. At the risk of sounding cocky, I am fairly certain I could date and so on if I tried in earnest, but I’ve only actively pursued a couple women my entire life, to no avail.

I am cynical about long-term relationships and discomfited by the intimacy involved in more casual arrangements. Early relationship excitement does appeal, except I am not an excitable person. I’ve been infatuated twice (see above), more because of unique circumstances (first crush, quarantine) than anything else. That’s unlikely to repeat, in large part because I’d rather it didn’t by now. This tangle of emotions has resulted in endless inaction, yet the notion of remaining celibate indefinitely rankles me. After all, You Only Live Once.

Hence, an ages old internal debate that I like to dub “Sense & Sensibility.” Sensibility would rather I leave matters the way they are, not because of any genuine hope of deliverance but just to enjoy the fantasy of larger-than-life romance a bit longer. Sense opines I’ve wasted enough time dithering and should just date casually; no need to become seriously involved with someone I am “merely fond of” if that offends Sensibility so much, but I could at least enjoy myself. This latter argument seems particularly persuasive when Sensuality (lust, but alliteration makes for alluring allegories) jumps in, but as a contestant it is woefully inconstant and so far Sensibility has enjoyed the advantage of being the incumbent.

With the quarantine hopefully coming to an end soon, the question of what to do is relevant again and therefore eager to torment me. Sometimes I manage to tell myself that, once meeting new people becomes feasible again, I’ll try asking some out and just date for the heck of it. But then the moment passes and I forswear all my plans. Hence, this letter. I am well aware of at least a portion of my flaws and it must be apparent by now that crippling indecisiveness is one of them.

Any advice would help. I should make it clear that my professional and social lives are going fairly well and I am overall content with my current situation, with plans to improve it further. So while I may seem dejected and do want to address this problem, its negative impact is mostly restricted to melancholy moods where I recite Keats to a suitably overcast sky. I try to balance that out by, I don’t know, singing AC/DC to a suitably overcast sky. Skies are nearly always suitably overcast this time of year where I live.

Thank you kindly,

Insert Clever Byname

So I’ve read through this letter a few times and honestly, the first thing that comes to mind is an eternally relevant quote from the sage: “Being clever’s a fine thing, but sometimes a boy just needs to get out of the house and meet some girls.”

If I’m gonna be blunt, this kind of screams of the sort of conversations I had in college at 3 AM with folks who a) made being Quirky And Weird their entire personality and b) were almost-but-not-quite too stoned to function. The problem is that Quirky And Weird isn’t the same as deep or interesting; it’s just weird, and to be perfectly frank, most of the time it just serves as a form of emotional self-defense. It may have started off with someone identifying with some loveable misfit from books or a movie or something, but more often than not it’s a not-terribly-productive way of keeping them from getting hurt by making sure nobody tries to come too close. It’s very easy to spin it to oneself as “I AM UNIQUE AND DEEP AND MISUNDERSTOOD AND ONLY SOMEONE WHO TRULY CARES FOR ME WILL LOOK PAST THIS/GET IT” but in practice, it ensure that they never have to deal with the actual risks that come from connecting with others. You don’t need to worry about being vulnerable when nobody tries to get close to you, after all.

Just between you, me, and everyone reading this, ICB… all I’m seeing here is someone trying to justify being afraid to put himself out there, dressed up in Very Clever drag. That’s why I’m left wondering: who are you trying to convince here, you or me? It’s not like I’m entirely unfamiliar with this approach; I coasted through high-school with the philosophy of “if you can’t dazzle them with your brilliance, baffle them with your bullshit.” Problem is, you can’t bullshit a bullshitter, especially one who knows this trick too. I mean, credit to your vocabulary and all but these are a lot of four dollar words to try to make “I can’t bring myself to take risks” sound deeper or more significant than it actually is. I’m certainly not somebody who’s opposed to having an affectation that makes you stand out in an unusual way but there’s a difference between a statement piece and self-consciously trying to act like you were born in the wrong time.

(God I miss the days when the folks doing this were just acting like they were part of the Rat Pack)

If we strip out the fancy language and equivocating, we come down to this: you’re afraid of what success would look like. You like the idea of relationships because a relationship in potentia is perfect. You can’t fuck up an ideal. You can’t have moments where you’re so irritated with them that you wonder why the hell you’re still together. You can’t have nights where you wonder if the way you tripped over your own ego (or your dick, for that matter) was so egregious that it’s going to bring the whole thing down. And, of course, you don’t have to drop the act and stop trying to use vocabulary and literary references as armor and actually deal with people as a person instead of as The Protagonist of a Gothic Romance.

(And seriously, you’re talking to an English lit major. Let’s be honest, most of those stories are tedious as fuck and the only ones that stand out as being interesting are because the folks involved are raging trashfires. LOOKING AT YOU, HENRY ‘WASHINGTON FUCKING SQUARE’ JAMES.)

The issue isn’t indecisiveness, my dude. The issue is being afraid of what any of this would mean. It’s being afraid, not just of rejection, but of having to connect with people on a primal level and open yourself up to them. It’s a fear of what it might mean if you met someone who actually did like you back and what would happen if you had to actually make things work, with all the risks that means.

Because here’s the thing: yeah, you’re gonna get hurt. Welcome to the world babies, it’s hot in the summer and cold in the winter and you’re gonna get your heart broken. That’s part of the process. You’re gonna fuck up otherwise promising relationships. That’s also part of the learning process. But the key word is learning — as in “learning from your mistakes” and “learning how to recover from fuck-ups“. It means learning that rejection sucks, but you’ll get over it and that while getting your heart broken feels like the end of the world, you’re gonna survive it, pick up the pieces and move on. And — just as importantly — you’re gonna start learning the difference between “attraction” and “love”, and why infatuation is neither the same thing nor something that even lasts very long.

Oh, and — assuming that you don’t have your head so far up your own ass you become a human Klein bottle — you’ll also hopefully learn that getting laid for the first time (or the first time in a long time) isn’t the same as “this is a person I could settle down with”.

But none of this can happen until you stop masking the truth with Very Clever lies. It’s not indecision, it’s fear. The sooner you admit it, the sooner you can face it. The sooner you face it, the sooner you can overcome it.

You say you could probably go out and date “if I tried in earnest” OK… so prove it. Drop the pretense, drop the persona and go actually talk to some girls. Put a profile up on Hinge, hit up some book clubs and just chat with people about something more than loving microbrews and reading Proust. Ask women out on dates, flirt, dance, dine and see where things go. Maybe it’ll lead somewhere. Maybe it won’t. Either way, it’ll be a learning experience?

Will you get hurt? Probably. Love isn’t meant to be safe. But then again, to paraphrase another literary sage: “THEN YOU WILL HAVE LEARNED AN IMPORTANT LESSON.”

Good luck.


Hello Doc,

I wanted to ask you for advice. I know this question was already answered, but I’m really having a hard time with dating boys who just want me for sex. Ever since I broke up with my ex a few years ago, I haven’t really been dating, and I’m a virgin.

I don’t want sex. How do I tell boys I don’t want sex and get the respect I deserve?

Not Interested

The answer to this is going to very much depend on an important — yet missing — clause. You say you don’t want sex. Is it the case that you don’t want sex yet? Or is it that you don’t want sex ever? That’s going to make a significant difference.

Now, in general, this is going to come down to using your words and establishing and maintaining strong boundaries. There’s been far, far too much ink spilled over “guys only want girls for sex” that treats this as a matter of “well if you do X correctly, then they’ll respect your wishes.” I’ve lost track of all the books, from The Rules to Think Like a Man, Act Like A Lady to whatever the hell it was Dr. Phil wrote up that treat this as some sort of magical spell that will change people’s minds… and the fact of the matter is that it won’t. Assholes are gonna ass, and no amount of “wait until X date to have sex” or “no sex before commitment” or any other arbitrary rule is going to change a dude looking for a low-effort lay into a committed boyfriend. As many a person has discovered, plenty of guys have hung around until they convinced their girlfriends to “finally” sleep with them and became profound assholes afterwards because hey, that’s all they ever wanted. Unfortunately, people will say whatever it takes if they think it’ll get them laid; the only difference is how much work they’re willing to put into any one person.

This is why my philosophy to this isn’t “don’t try to change the asshole into a boyfriend”, it’s “exclude the assholes as early and as thoroughly as possible”. There are no words that will “make” someone respect you. Nobody, especially horny teens and twenty-somethings, have ever said “woah, I was just trying to get into your pants, but your ‘no sex before three months in’ changed my mind and now I want commitment”. It’s about chasing off the assholes and finding the guys who are on the same page as you and who will respect your boundaries and wishes.

You don’t want sex; whether that’s for now or for good, that’s something that you should be up front about. The majority of folks who are looking for a relationship are looking for a relationship that includes sex; if sex isn’t on the table, then that’s something that they should know. This helps make sure that you’re dating the people who want the same things you are. Yes, it means that folks will peace out upon hearing this. That’s good. That’s how it should be. It doesn’t mean that they’re jerks, it just means that they weren’t right for you and you weren’t right for them. If they want a sexual relationship, then pursuing something with you is only going to waste their time and yours.

Now how you roll this out… well, that’s gonna vary, and a lot goes back to that missing clause; whether it’s a “yet” vs. an “ever”. My general thought on disclosing information, particularly stigmatizing or polarizing information, is that if it’s not immediately relevant, you can give it up to three dates. This gives someone the chance to get to know you for you, rather than whatever stereotype may exist in their head — whether that’s about someone who has genital herpes, ethically non-monogamous or who would want to wait for sex until marriage. Other folks disagree, but they’re also not writing this column.

However, the more relevant that information is, the sooner it should be brought up… and it should be brought up before it’s going to impact things. If it’s an issue surrounding sex — whether it’s STI status or not wanting to have sex until X time — then it needs to happen before sex is imminent and preferably before things go from kissing to “making out that’s going to potentially involve genitals in some way, shape or form.”

In this case, if the clause that’s missing from “I don’t want sex” is “ever”, then that’s information that should probably be included right from the jump. As I said, the majority of people you might date are going to want a sexual relationship. If that’s simply not on the table, ever, then that’s something they should know in advance so that they can make an informed decision. And you should be clear — bluntly so — that it is “not ever” if that’s the case; the last thing you want are folks who think that it might happen and getting increasingly frustrated when it doesn’t.

(Now, to be clear: asexuality is wide and varied and there’re some ace folks who do have sex because their partners like it and they like pleasing their partners. This is why I’m fairly firm that defining the relationship discussions should include talking about the frequency and type of sex you both want or don’t want. It helps make sure that everybody is on the same page.)

Regardless of whether it’s “yet” or “ever”, what you don’t do is roll out this information like you’re informing them of a curse on your bloodline or that this is some horrible flaw. You don’t want sex; that’s just a fact about you and not something to apologize for. You want to treat this information as something matter-of-fact and straight forward, not something you feel ashamed of. It’s relevant info about who you are, but it’s only one thing about you. How guys respond to this, however, will tell you everything you need to know about them. Guys who say “ah, ok, not what I’m looking for, best of luck to you?” These are good guys who just weren’t compatible with you. Guys who say “wait, what? Why the hell not? What about….?” or “Well, I bet I can change your mind” are guys to cut loose with a quickness; they’ve just displayed their assholery like the tail of a particularly shitty peacock.

Once you’ve established what you are and aren’t up for, you need to be willing to stick to it. You’ve laid down your boundaries surrounding sex, but having boundaries means that you have to enforce them as well. This means that you don’t want to tolerate guys who think that “never” means “wait and I’ll change my mind” and “yet” means “convince me”. Getting the respect you deserve means that you don’t put up with people who disrespect you. Guys who push at your boundaries and try to get you to do things you don’t want or aren’t ready for yet are guys who are demonstrating that they don’t respect you.

It’s one thing if they brush up on your boundary around sex and then, after you remind then that no, this isn’t a thing you’re up for, recognize and respect your decision. A guy who hears “I said I’m not interested in X, remember?” and says “Oh, right, my bad” and drops it? They’re showing that they do respect you; they hit up on your boundary and have said “whoops, sorry” and stepped back. Those are guys worth dating.

On the other hand, guys who constantly push at your boundaries even after being reminded that they’re there, or who argue with you about having those boundaries at all, are dudes to kick to the curb like the week’s compost. These are men who don’t respect you or your wishes and are trying to get you to give into what they want, regardless of your feelings on the matter. These are the dudes to bounce out of your life so hard that they enter geosynchronous orbit, sooner, rather than later.

And in fairness: it can be tough to do this. It can be hard, especially for women, to stand up for themselves when a guy is making a fuss. It feels rude and uncomfortable to be that direct and straightforward. But it’s also important that you do so. Gently hinting or reminding someone is ok… the first time. The second time, it’s time for the clue-by-four, followed by The Chair Leg of Truth. And that truth is that they are now on the train to DUMPED, population: Them.

Will being up front, especially in the early stages, mean that you’ll have more rejections and fewer dates? Yeah… there’s not really any getting around that. But it also means that those were folks who weren’t right for you in the first place; all that’s happened is that you’ve saved yourself time and energy and now you’re free to go find men you are compatible with. This isn’t a bug, it’s a feature, and one that helps ensure that the guys you do date? Are the guys who you should be dating.

Good luck.

This post was previously published on doctornerdlove.com.


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The post Why Am I So Indecisive About Dating? appeared first on The Good Men Project.

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