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A Nice Guy Tells You How to Win His Heart

by Jane Smith

I’ve been putting together some of the best comments left by guys over the last few months, but today I’m featuring one left just this morning that stands on its own as a post. Guys tend to leave more comments than girls do (Get with it ladies!), and I’ve learned a tremendous amount from them. Having a window into the male psyche circa 2010 is valuable currency in my world.

Dilithium has become a pretty regular reader here over the last few months, and he often leaves thoughtful feedback. He is extraordinarily smart, and a great writer, so he’s always a delight to read. It’s also abundantly clear that he is a NICE GUY. He speaks affectingly about the plight of less aggressive males in today’s sociosexual marketplace.

If you have had it with the guys in your social scene, and wish there was some way to snag that cute guy in your bio lab or the smart, good guy in the IT department at work, read what Dilithium has to say. It’s a brilliant look into the mind of a potential Dad.

Unfortunately, Dilithium can’t introduce you. You’re going to have to initiate conversation on your own, something that women often find intimidating. The good news, though, is that your initial goal is not a hookup. It’s pleasant conversation. Start there.


How to Get With a Nice Guy, and Have Fun Doing It

by Dilithium

You might actually find this surprisingly difficult! and it may be more work than you’re interested in doing. But the potential payoff is huge, and that’s why I’m here to help.

How you appear to him:

If you’re at least reasonably attractive, reasonably intelligent, and not apparently crazy or shallow, then to him you are: the Hope Diamond, but locked in a 12-digit combination safe at the other end of a tightrope stretched over a pool of alligators. In other words, you are a great and promising treasure, but he fears that to get anywhere with you he needs to do a whole series of things exactly right — one slip-up and his chance is gone.

Why does he think this way? Because of his prior experience. If he’s the socially un-fluent type, then chances are he didn’t do very well in high school; more exactly, he probably tried to make time with some girls, but very often failed; and, even more exactly, not being socially fluent he failed but doesn’t know WHY he failed. Let’s face it, high school girls are not known for telling the truth in plain language, especially when rejecting someone; the boy who can’t read social cues very well is only left to wonder, What did I do wrong? After several disappointing years of this he, quite understandably, comes to see girls as basically flaky and inscrutable — as 12-digit combination safes, where if you don’t do everything exactly right, you’re gone. Keep that image in mind.

If you want to get with this guy in later life — he has a lot of advantages, too, as we will see — then your basic job is to demonstrate convincingly to him that you are not the 12-digit safe, that you will not require him to run a gauntlet of baffling tests and that you will not dump him the first (or second) time he makes a mistake. Remember, coming out of high school that’s his image of how all girls are — you have to actively work to overcome that image if you want to be worth his time.

My primer:

1. Be physical, but not necessarily sexual, early and often.

Your nice guy, even if he’s handsome and fit, probably has hang-ups about his body. As a woman you might be surprised to learn this — you thought only girls had body-image trouble — but it makes sense if you consider his past experience. He’s been treated almost like a leper, basically untouched and untouchable, for years in a row; even if the real source of his problem was elsewhere, he’s probably formed the idea, even subconsciously, that his body is somehow physically repulsive.

You can correct this impression — you want to! — but there are better and worse ways to do so. My advice is, don’t jump his bones in one big go right away (see below); better is to do a lot of small things to show, quietly and continually, that you enjoy his physical contact. You don’t need to grope him or fall all over him; just hold hands, put your arm around his waist, lean against him sometimes when you walk. Continuous, small reminders are what will really be convincing.


2. Don’t command a performance that he can’t (yet) deliver.

Suppose you do indulge the urge to grab his crotch and say “All right, big boy, let’s give it a go!” You might think of this as giving the ultimate compliment, fulfilling every young man’s dream; but the most likely result in your nice guy is panic. Not that he’s rejecting you! Trust me, he appreciates your enthusiasm! But you might not realize that you’ve put him in a tough spot: as he sees it, he now has to deliver a performance that he has little or no experience giving. He’s thinking, what do I do now? Should I feel her up? should I try to take her shirt off? should we just kiss for a while? What’s the right thing to do next? The truth, which is that any of those might be just fine, will not occur to him; instead of just doing whatever comes naturally, he fears that if he does the wrong thing at the wrong time you will change your mind and bail out.

Why should he think this way? Again, most likely because that’s what happened to him before. Imagine a standard high-school-age scene: a girl and a boy are alone together, hot and heavy for the first time; but at their age it’s often the blind leading the blind. She’s expecting him to lead the way, but when she finds out he’s just as inexperienced it’s not uncommon for the girl to call a halt to the proceedings. Different boys react to this in different ways. The self-centered ones, budding misogynists and future players, may blame the girl; while the now and future nice guy will more likely blame himself, able only to wonder What did I do wrong? Thus he builds up the 12-digit safe image: if you don’t know exactly what to do next at every turn, then you might as well not start.

Don’t worry! this doesn’t mean that you can’t have fun sex with a nice guy! It’s just that you’ll be better off if you don’t frame the situation in such a way that he’s giving a high-stakes command performance. Make it absolutely clear that you’re not going to grade and criticize his every move, and that you welcome the spirit of whatever he wants to try. This is probably true, you just have to get it across. And try some stuff yourself! nice guys, unlike alpha jocks, are usually very receptive to women taking the initiative.

The same principle applies in many other, daylight situations. If your guy is not a fluent talker, then a dinner date may be a long and painful experience early in a relationship. You may just want him to relax and talk about whatever he wants to; but he may see it as a command performance, that he has to work to impress you — over and over again, every five minutes for two hours. This is one reason I wouldn’t recommend dinner dates before two people know each other fairly well; a restaurant setting is blank, it doesn’t give you much to work with. Better is an event, a parade, or even a walk around town, where new stuff is always coming into view and gives both of you something to talk about.

The bottom line here is, try to avoid setting up situations in which your guy feels he has to perform something he’s not good at; it will be painful for him, and make him look less attractive to you.


3. Visit him when he’s at his best.

The flip side of the same token is that it’s within your power to make your guy look more attractive to you. (Isn’t that a fun idea?  Having a magic wand that does nothing to you, but instead makes other people prettier for your benefit?) The key here is to spend time with him while he’s doing something he’s good at and that he enjoys. It may be playing a sport, or an instrument, or fixing up a car; almost everyone is good at something. You will appreciate seeing him happy, relaxed and masterful, and he will appreciate the chance to show off for you successfully. Note that this tactic is specific to nice guys: nice guys get a kick out of the idea that they can impress a girl, while alpha jocks consider it beneath them even to try.


4. Feel free to be your best, and don’t even think of bimbo-izing.

This is another, subtler advantage of going with a nice guy: around them, it is to your advantage to show how smart and skilled you really are; they’ll enjoy and appreciate it, where alpha jocks would be bothered and threatened. The reason why has to do with different approaches to ego support.

A quick, common, though unimaginative attempt at ego support is to display yourself as being lesser or weaker than the other person: “Oh, Rocko, you’re so strong, can you open this pickle jar for me?” This is the kind of support that alpha jocks like to get; their security comes from women’s insecurity, from the idea that they have higher value and so women will be drawn to them and afraid to leave them.

A different approach to ego support is, be as good and amazing a person as possible yourself, and then elevate the other person by singling them out for your favor. This is the kind of support that nice guys like to get. Remember, as a reasonably attractive woman you start the relationship with a nice guy in a position of superior power; you don’t build him up by tearing yourself down. Once he’s convinced that you really go for him, then everything good about you — your skills, your culture, your intelligence — reflects back positively on him; he’ll enjoy bragging about how competent and amazing you are. So don’t act like a bimbo, even for a moment! Be your best, it’s all to the good. You may find this difficult to believe, but among nerds (typically a subset of nice guys) it’s actually a high compliment when someone says “Man, your girlfriend is smart!”


5. Don’t ever flake out, or do anything that even faintly smacks of a power game.

As mentioned above, if you’re a reasonably attractive woman then you will start a relationship with an inexperienced nice guy in a position of superior power. Whether it’s true or not, he will likely believe that you can get another guy at the snap of your fingers, while he can’t do the same, which gives you the upper hand. Some girls find this not to their taste; and if so, then they are just advised to stay away from these guys. If you’re willing to live with the upper hand, though, then my advice for you to be happy with your nice guy is simple: never, ever show that hand. If you try some sort of power move, to yank his chain even a little, it won’t end well for you. At best, he’ll be resentful of having his insecurity exposed; at worst he’ll respond by turning himself door-mattish; and you don’t really want either of those if you’re at all a decent person.

The problem is, you may think you don’t want to do anything like this, but everyone does some of it naturally, without thinking. The simplest example is flaking, ie not showing up to an appointment, or showing up very late. Making other people wait is a traditional assertion of power, used by everyone from senators to DMV clerks. You probably do it, along with everyone else, without even realizing it. My point here is, you should be extra-careful not to flake out or otherwise overtly demonstrate power when dealing with an inexperienced nice guy, it’s really just asking for trouble. If you do have to miss a date, be absolutely sure to show explicit contrition later, even if only symbolic (bringing a cupcake is a good start).


Awww, who couldn’t fall for a guy who appreciates a cupcake? I’d say sign me up, I want one of these ASAP, but the truth is, I married one of these guys 25 years ago. He is all that.

I don’t know anything about Dilithium’s personal life, but it occurs to me that he’s quite a catch himself.

Thanks, Dilithium, for your time and your considerable expertise!