Hello, Internet! Welcome to Ask Dr. NerdLove, the only dating advice column that managed to rescue Quickclaw and Rhonda in Pitfall II. That's right! ATARI 2600, BABY.

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This week, one reader is getting tired of being constantly told he's "too nice" to date - so how does one become more exciting to potential partners? Meanwhile, another reader wants to know: how do you keep a relationship casual when all you want's a friend with benefits?

Ready to challenge yourselves? Let's do this thing:

Hi Doc:

I'm 25 years old and recently decided to get back into dating after taking a break for the past several months. Dating is tough for me, but I know that if I change a few key things, I could be successful.

What I've noticed about my interactions with women is that while the conversations themselves aren't bad or awkward, they're very flat, and it seems like girls don't find me "psychologically" interesting - basically, they think I'm boring.

My female friends often tell me that I'm "too nice" and that I "need to be more confident", and I've realized that I'm kind of the typical "Nice Guy" in this regard (which is bad) but my issue isn't the "friendzone", there's just….no zone. I believe in being open and honest with people, I don't try to manipulate women into liking me or having sex with me by playing head-games, but at the same time, I know I'm failing because I don't present any sort of challenge to them.

I'm okay on paper - I'm not bad looking, I work out, wear clothes that fit my body shape, I have a pretty good job, I'm finishing up my masters degree this semester, and I play the drums. I'm pretty comfortable with who I am and what I want too, but I make a lot of mistakes, and I know that the way I approach women isn't enticing, sexy, or attractive. While I usually don't have a difficult time getting to know new people, even women, put me in front of an attractive girl and I completely fall apart. I don't have "game" and I'm not a smooth talker, so when a girl actually gives me a chance, there's never any "hook".

Again, the conversation isn't bad or awkward per se, but I can tell when that girls are just being polite and waiting for me to go away - they never seem even remotely attracted to me. So while I think there are things about me that are interesting and that I'm a good guy, simultaneously, I know that girls don't really care about any of that - they want someone who excites them, who makes them feel a certain way, and I don't do any of that. I don't know what to do, let alone how.

Doc, please help!

Sincerely,
Boring and Easy

One of the things I've noticed a lot of guys do is that they give themselves a false dichotomy. They tend to assume that there are only two ways of interacting with women: being a passive nice guy (as opposed to a Nice Guy™) or a manipulative, head-game playing shitbag. But being attractive and flirty doesn't mean being a Game-spewing player who tries to neg women and play cocky-funny status games, nor does being a good guy mean being duller than dry toast.

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When women tell you that you're too nice, what they really mean 9 times out of 10 is that you're passive. You have a lot of attractive potential, but you're presenting yourself in the dullest, most passive way possible. I suspect that when you talk to women you're interested in, you're terrified of making a mistake and accidentally offending them and, as a result, play things as safe as possible.

And therein lies the problem. When you play things too safely and take no risks then either you end up boring potential dates or convincing them that you're not actually interested in them in the first place. You give them no material to work with; why should they be intrigued by you when what you're giving them is this bland pablum?

This is part of why women seem to love assholes; it has nothing to do with "assholes get all the women" and everything to do with the fact that they know how to present themselves and they put themselves out there. They're making a point to flirt, to be engaging and - critically - making a move. That's part of why your friends are telling you that you need more confidence; you're never going to get anywhere unless you take some risks.

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Women aren't going to be interested in you unless they feel some chemistry - that spark of attraction that intrigues them both physically and emotionally. This means that you have to engage them on both levels. On the physical side, you have to be willing to flirt, to tease and to touch and build the tension between the two of you. Are you giving her strong eye-contact, or are you avoiding looking at her? Are you willing to banter a little, or are you being agreeable? Are you touching her - say, the back of your hand on her upper arm as you reach the emotional high-point of a funny story?

Part of physical chemistry is maintaining a push-pull dynamic; build up some excitement and then draw back. Think of a roller-coaster; the build-up of anticipation as you ratchet up to top what makes you crave the feel of that first drop. If all you have is the drop, you get desensitized and bored. At the same time, too much interest is as unexciting as too little interest. It's important to let her know that you're interested in her romantically or sexually - ambiguity is an attraction killer - but if you're going overboard with being available or wanting her to go out with you, you're going to come across as needy and neediness is the anti-sex equation.

On the emotional side, you want to connect with her: what do you have in common? What should she like about you and what should you like about her? Are you relating to her on an emotional level? Are you making her laugh, making her excited, making her feel? Are you telling fun stories about your life? Are you connecting with her passions and sharing what you're passionate about? Are you finding out what makes her tick and finding ways to show that you get her on that level?

It's important that you connect on both a physical and an emotional level. If you've got nothing but physical chemistry, you risk them thinking you're hot but not really worth it. If you've got nothing but emotional chemistry, you've found another BFF instead of a lover.

Now being flirty and generating chemistry doesn't mean that you're being manipulative; it just means that you know how to interact with people in an attractive way. You aren't tricking them or pressuring them - you're still being your authentic self. You're just showing them how awesome you are. If you're not sure how you can be flirty, even sexual, without being a creep, then I might suggest studying one of the greatest nerd dating role models in genre entertainment: Captain Jack Harkness. He's sexual without being a creep, forward without being pushy and above all else: considerate and safe. He's the very model of the collaborative mindset when it comes to sex: "Here's this awesome thing we can do together" rather than the antagonistic "what do I have to do to get what I want?"

Here's the thing: I know damn good and well how nerve-wracking it can be to put yourself out there that openly. You're worried that you'll make mistakes and offend people… and in full honesty, yeah, you're going to fuck up sometimes, especially while you're learning.

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But here's the trick: if you fuck up? Apologize. Not a "sorry but you took that wrong" or "I'm sorry you were offended" non-apology but a sincere "I'm sorry I made a mistake". The difference between a creeper and a cool guy who put his foot in his mouth is how he handles things after he fucked up.

It's going to take some time and practice to find the way to put yourself out there that syncs with your personality, B&E. But the more you work at it, the better you'll do.

Good luck.

Hey Doc,

Have a quick question for you. I'm looking to get a Friends with Benefits situation, and so I'm looking for girls that want the same thing. Met a girl on OKCupid, her profile says she's looking for Short Term dating. She's a busy student. Seems good, right?

Had a first date where we talked for a long time, there was some connection there. I mentioned I'm moving in a few months, though I didn't specifically say "so I'm looking for something casual."

I'm trying to arrange date 2, and she seems up to it, but I'm wondering when to tell her I'm looking to be Friends with Benefits? Girls tend to see me as long-term-relationship guy, and I think it might have to do with the fact that I take so long to say things like this.

Do I just do something fun and flirty for a 2nd date, then at some point say "hey, you're really fun, you know I won't be here for too long, so how about we make this a friends with benefits thing?" We haven't kissed yet, so should I wait until we've already done so?

(The other question is, how do I tease out of her if she's open to that sort of thing? I don't want to have a fun date, have her thinking "this guy could be long term material", then talk about short-term dating and she feels like she's somehow failed, or it's a statement that I'm not that into her).

Thanks,
J

First things first: if you're looking for something casual, you have to present yourself as wanting something casual. It's better to be up front with this - it gives people who are looking for a long-term relationship the opportunity to opt-out as well as helps ensure that there aren't any mixed signals or misunderstandings.

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One of the things that guys tend to do is give hints - either accidentally or intentionally - that they're open to a long-term relationship. Sometimes it's simple ignorance; it's easy to not see how you're giving the wrong impression. Other times it's straight manipulation - they're implying that they might want something long-term as a way of baiting women into something casual now.

For example: in online dating profiles guys will say something along the lines of "not looking for anything serious, so let's just see how it goes". This suggests that they're at least open to the potential of something long-term with the right person. It's understandable - being up front about only being interested in a no-strings-attached sexual relationship is going to turn off a lot of people and many guys don't want to limit their dating pool that way. However, being straightforward about only wanting something casual means that the people who do respond will be on the same page as you.

Another way people send the wrong signals is that when they're dating somebody, they'll establish a relationship frame instead of a casual-dating one. When you're taking someone on a romantic date - candlelit dinners, carriage rides in the park, etc. - you're sending a different signal than if you're, say, going bowling or swing-dancing. Similarly, they may talk about the future rather than staying in the now. When you start talking about future plans, unless you're very specific you're giving hints that you see your date sharing that future with you.

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Don't get me wrong: I'm not saying that romance is a bad thing or that you can't talk about things you might want to do beyond next weekend. However, if what you're looking for is no- or low-commitment sex, then prioritizing romance and intimacy is sending the wrong signal and is apt to end in confusion and hurt feelings.

Now with your specific situation, J, you want to keep things light. You want to focus on having fun, exciting and active dates - anything that gets the heart pumping and the blood flowing is going to be more arousing instead of inspiring feelings of intimacy and commitment.

Don't take it for granted that she's not going to want something casual. You've already told your date that you were moving soon. Unless she wasn't listening at all, you can assume that she's aware that there's no long-term potential here.

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I wouldn't try to set ground-rules yet in any case - you've only had one date and you haven't so much as kissed yet. She may well decide she's not into you in the short term, never mind the long term. Trying to have the defining the relationship talk at this stage is so hilariously premature that it's going to come off as seriously weird. The best time to make sure you're both on the same page is before you have sex, otherwise you risk coming off as having sent the wrong signals to get what you want.

Let her know that you like her, but you're not up for anything committed (you're moving, after all) and you want to make sure that she is ok with that. If she asks what you mean then explain that you don't want and can't offer anything more than a casual sexual relationship. I wouldn't use the phrase "friends with benefits" unless absolutely necessary because, frankly, it's awkward as hell.

Make sure you both understand each other before continuing the relationship; be clear about what you mean when you say 'casual" and define your terms. I realize it sounds clinical and can feel like you're negotiating a contract a la 50 Shades of Grey, but there's a point to all of this. If you want to avoid hurt feelings or any miscommunication, then you want to make sure you both understand what you're expecting from one another.

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Once you establish the ground rules - as it were - of your relationship, make sure you stick to them. Just as some people will pretend to offer commitment to get a casual relationship, some people - men and women - will agree to a casual relationship with the intention of trying to push their partner into something more committed. It's not fun when this happens and it sure as hell isn't fair. Be willing to enforce your boundaries.

And for future reference: OKCupid isn't a bad place to find casual NSA sexual relationships - I've had plenty of success that way - but you might have better luck and less potential confusion on Tinder.

Good luck.

Have you escaped from a toxic relationship? Did you get over an inconvenient crush? Share your thoughts and experiences in the comments and we'll be back in two weeks with more of your dating questions.

Ask Dr. Nerdlove is Kotaku's bi-weekly dating column, hosted by the one and only Harris O'Malley, AKA Dr. Nerdlove. Got a question you'd like answered? Write doc@doctornerdlove.com and put "Kotaku" in the subject line.

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Harris O'Malley is a writer and dating coach who provides geek dating advice at his blog Paging Dr. NerdLove and the Dr. NerdLove podcast. His new book Simplified Dating is available exclusively through Amazon. He is also a regular guest at One Of Us. He can be found dispensing snark and advice on Facebook and on Twitter at @DrNerdLove.