DEAR DR. NERDLOVE: I have an odd question for you. I’ve been working my way towards self-improvement and trying to get to a place where I’d be someone women would be proud to date. While I feel like I’ve made some serious strides, dressing better, changed my hair and my diet, working out more, practicing talking to people and trying to flirt and all that, I still freeze up when it comes to actually going on a date.

Every time I get to the point that I feel like I’ve got a good connection with someone and they like me, as soon as I get ready to actually pull the trigger on asking them out I start imagining all the ways I could mess up a date or things could go horribly wrong. Like I get to the restaurant and my date orders something insanely expensive or I just can’t afford the bill or the restaurant lost our reservation or something. Or maybe I try to take her out to a club but other guys muscle in and push me out of my own date. Or I try to plan a date that I think is cool but she thinks it’s boring or cliché or tired and then she gets online and starts talking about how I’m another guy who took her on a dumb date and or something.

I thought I’d solved all my dating problems and now I’m stuck with the dumbest problem in the world, like I made it to the finish line and then it turns out there’s another ten laps to go and everyone’s passed me already.

How do I actually plan a date that women would want to go on with me and how do I make sure none of these crazy things go wrong and waste all the hard work I’d put into myself? This is both on the apps and in person, by the way.

Red Flag On The Last Lap

DEAR RED FLAG ON THE LAST LAP: Good news, RFLL: this is just anxiety f--king with you. The things you’re worried about are either not nearly as bad as you think they are or are so unlikely that you probably have better odds of winning the MegaMillions drawing.

That’s not to say that annoying things can’t happen when you’re on a date. Chaos gets into every system and s--t happens to everyone, but half the stuff you mention worrying about is the stuff of the fantasies of dodgy subreddits and poorly written television.

(Plus, if you’re on an actual date with someone who’s willing to ditch you to go off with someone else, that’s more of a “you dodged a bullet” situation.)

So instead of worrying about the dude at the club “stealing” your girl, it’s better to focus on the things that are much more plausible. Fortunately for you, almost all of these are either easily prevented or mitigated with a little foresight and preparation.

Let’s start with the obvious: have a date in mind before you ask someone out. One of the things I’m always telling my clients is that if you’re going to ask someone out, never leave it ambiguous. That means no asking to “hang out some time” or “get together” or “maybe we could… later”. You want to give them something concrete to actually say “yes” to, rather than “I’d like to take you to some nebulous event at an even vaguer time, under circumstances that may or may not be a date.”

So rather than asking to “get a drink, sometime”, you want to say “Hey, there’s a great wine and tapas bar that has an incredible happy hour on Fridays. I’d love to take you if you’re interested.”

Alternately, if you want to get a little creative and take her on a date she’s not likely to have been on before, you can try combining a couple different things into one date. I’ve had great success with “hey, how do you feel about pinball and craft cocktails? Awesome, there’s a vintage arcade that’s next to an amazing Prohibition-era cocktail bar; what do you say to high-score gets the first round?” or “what’re your opinions on milkshakes and swing dancing? Well, there’s a weekly swing night at the Fed every Thursday, and there’s a diner with incredible desserts a couple blocks away…”��Proposing a specific date when you ask her out means that she knows what she’s agreeing to; if it’s the sort of thing she’s not interested in, she’s got the opportunity to say “no, thanks” or even to suggest a different idea.

Plus, having a specific date in mind means that you can solve a lot of logistical hurdles in advance. It means that you have the opportunity to scope the place out, find out when it’s the most busy, check the prices, see if they have any discounts or specials that make it more affordable, find the best places for parking and so on. This cuts out a lot of the first date misadventures before they even have a chance to happen.

Next, get yourself on the apps. Not the dating apps but ones like OpenTable or Resy or Toast. These are going to be your friend, not just for making sure you’re not waiting two hours and getting increasingly hangry but in case things fall through at the last minute. I’ve saved a lot of evenings by being able to make split-second alternative arrangements when plans A through C blew up for various reasons. Plus, many of them have services that will notify you of any last-minute openings at those hard-to-get reservations.

The other thing I would suggest is know what you can afford before you propose a date. There’s nothing wrong with dates that are relatively cheap or even free; it’s about the two of you getting to know each other and seeing if there’s mutual interest and chemistry. You want them to connect with you, not with what’s in your wallet. A good date isn’t defined by how much you spend, it’s about how much the person enjoys their time with you. A visit to the zoo or a museum and a couple of ice cream cones can be a much better date than dinner at the swankiest see-and-be-seen bar or restaurant, especially if that’s not your normal scene.

Trying to woo someone by wining and dining them at expensive restaurants or pricy dates is a lovely idea, but you’re not trying to bowl them over with how much you spend on them. And if they’re someone who’s going to insist that they “deserve” to be taken to the places you can’t afford? Well that’s not someone you want to be dating in the first place.

Oh, and one more thing: pick dates that are fun, interesting or exciting, not ones that are pleasant. Pleasant is nice, but it’s also not memorable. You want dates that make you stand out, that they’ll not just enjoy but remember and have such a good time that they can’t wait until the next one. That could be a skee-ball competition, racing go-karts, a visit to the aquarium or wandering the local open-air art bazaar or market. Do some research in advance, find out what’s happening in your town that you’d love to go try anyway and let those guide you when you’re making plans.

Good luck.

Please send your questions to Dr. NerdLove at his website (www.doctornerdlove.com/contact); or to his email, doc@doctornerdlove.com

DEAR DR. NERDLOVE: I’ve had my relationship problems. I mean, who hasn’t? But those past problems keep haunting my every decision currently. I used to be all “I’ll ask this girl out and if she says no, I won’t let it bother me.” and now I’m questioning every single move I make on every crush I have.

I just recently started to talk to this girl. She’s amazing to talk to, and we talk almost every day. The only problem we actually have is that she lives in New Zealand, and I’m in the US. we’ve talked about me buying a ticket for her to come over to the US or me buying a ticket to Auckland (Not the city she lives in by the way, it’s just the cheapest flight I could get). She’s also been saying we should do normal friend activities like playing games and seeing the sights, which makes me think that confessing to her is pointless in its own regard. I’m okay with her being a friend, as I can let these feelings run their course. The real problem is how I feel about confessing to her if the chance arises.

I wanna tell her how I feel about her, but every time I find an opportunity, these thoughts get into my head about her either rejecting me and breaking my heart or dating me just long enough for me to fall for her even faster than I am now, just to let me hit the pavement on the way down. It makes me instantly drop the confession and leaving her extremely confused. I’m really scared because I’ve gone through that pain and my last relationship’s breakup made me relapse and have a depression episode. I’m also deathly scared of getting too attached to this girl, because it just makes me hate myself that I need a person to determine whether I feel happy or not.

I need some help as to whether I’m just being paranoid or not… I probably shouldn’t be looking for a long distance relationship anyways but whenever I try to look around for someone to be with here, I’m left feeling disappointed I even thought of going out with them.

To Jump or Not To Jump

DEAR TO JUMP OR NOT TO JUMP: Ok, TJNTJ, I’m going to skip over my usual rant about why I’m generally down on making love confessions, because honestly, that’s the least of the issues here. Instead, I’m going to cut straight to the chase: what you’re feeling isn’t anxiety or paranoia, it’s an accurate reading of the situation and you don’t like what it’s telling you. Your New Zealand friend is giving you the wave-off.

Take it from someone who has been there and done that, down to the “flying out a stupidly long distance to see someone on the off chance of making something happen”: you aren’t hiding this as well as you think, nor are you being subtle about things. I can promise you that she knows exactly how you feel and she’s trying to tell you to dial your expectations back by a factor of a thousand.

You don’t say how long you’ve been talking to her, but it sure as hell doesn’t sound like its been even a year, yet. That’s premature at best, especially for someone you’ve never met in person. If I were a betting man, I’d lay cash money on her hoping that maybe this impulse to come visit is going to pass and you’re going to go back to being a friend to talk to online.  

You’re worried about getting too attached to this person, but you’re also barreling headlong into doing precisely that. I mean, for f--k’s sake, you are already talking about making an incredibly expensive purchase – and that’s without factoring in things like lodging or actually getting to her city – to go see someone that you barely know. Even allowing for the absurdity of this at the stage of your relationship with her, throwing that level of money at a nascent friendship is a literal over-investment. This is precisely the sort of thing that leads to what’s known as the sunk-cost fallacy; you feel like you have to commit even harder to something because otherwise you have to admit that the time, energy and/or money you’ve invested into it has been for nothing. That’s incredibly damaging to the ego and to your hopes, and so it’s easier (emotionally speaking) to throw more at it in hopes of recouping your initial investment.

So the first thing you need to do: put the “going to see her” fantasy on pause for a long, long time. You’re making more of this than is actually there because it’s less about her and more about filling a need that you’ve been neglecting in your own life. And from the sounds of it that need is “dealing with the end of your previous relationship”. It sounds like you haven’t come to terms with it – not in the sense of “you haven’t accepted the break up” so much as “you need to take stock of how this affected you and address the wounds and questions it brought up”.

I’ve talked about the irrational fear of “rebound” relationships before. Well, congratulations; you’re looking at an actual rebound here. You’re doing something I’ve seen a lot of folks do: they have a break up that his them like a truck and then develop an excessive crush on someone – often someone unattainable or out of reach. It’s a way of trying to plug the hole they feel in their lives where that person used to be. Except that hole isn’t the absence of the person, it’s their own feelings about themselves and what that relationship (and break up) represented. The hole doesn’t need to be plugged or have someone else slotted into it, it needs actual closure. And – as I’ve said many times before – closure is something you have to give yourself.   

What you need, more than anything else right now, is to recognize this for what it is – an attempt to avoid pain – and to let go of this crush. You don’t have to let go of your friend, but you do need to put the desire for more aside. This isn’t going to go anywhere good; all it’s going to do is prolong and exacerbate the pain by adding new complications on top of it.

You’re carrying a lot of hurt around right now that’s directed inward and you’re trying very hard to numb yourself to it. While that’s an understandable and very human impulse, it’s also going to work against you. Avoiding or not feeling the pain isn’t the same as treating the underlying cause. Numbing it may make it possible for you to function in an approximation of normalcy, but it’s just putting off the inevitable. And you can only do it for so long, especially when you end up adding to it.

Instead of putting the money towards a plane ticket (and a passport and travel expenses and…) you really should put that money towards talking to a counselor or therapist. Think of this as doing physical therapy and rehab after an injury; right now, you’re doing the emotional equivalent of trying to walk off a torn muscle with some Advil instead of actually getting into the doctor’s office.

It’s time to stop trying to play injured and go deal with the injury. Let this crush go and focus on your emotional health. Love and relationships will be waiting for you when you’re in better working order.

Good luck.

Please send your questions to Dr. NerdLove at his website (www.doctornerdlove.com/contact); or to his email, doc@doctornerdlove.com

DEAR DR. NERDLOVE: Long (and I mean LONG, at least ten years) time reader, first-time asker here.�My problem has less to do with my lack of success in dating and romance, though I do have that. It’s more to do with my sexuality as a whole, and whether it’s ultimately holding me back, or even harmful.

I’m a cishet white guy, almost 30, normal-looking, not impoverished but not rich either, and I have what you might describe as a sophomoric libido, which I find kind of embarrassing.

I’ve had two very brief relationships and a single one-night-stand where I couldn’t even get it up, and consequently I fantasize about being in exactly the opposite situation – having lots of sex with lots of conventionally-attractive young women.

I am very much aware that our entire culture has been oriented entirely towards people like me to the exclusion of anyone else for a very long time. But when I read a pulpy horror or fantasy novel by a male author and he starts describing a female character’s body in leery detail (the sort of thing you’d see on r/menwritingwomen), while I recognize it as being something that might make someone who isn’t a straight man uncomfortable, I cannot deny that I ENJOY reading passages like that, to the degree that I actively seek books of that sort out. The result is that I make myself feel ashamed and titillated at the same time on a pretty regular basis.

The same goes for sexualized designs for female characters in video games, heaving-corseted heroines in 70s exploitation movies, and so on. I LIKE seeing these objectified images, and it makes me feel bad, since I know that culture is deliberately trying to move past that sort of thing to make the media landscape more friendly to people who aren’t… well, me. So bad I worry that it might come across as off-putting should any potential future partners or platonic female friends find out about it.

I recently read bell hooks’s book “The Will to Change: Men, Masculinity, and Love” (not a flex, it made me feel bad and I didn’t enjoy the experience) and I couldn’t deny that I saw myself in her description of toxic masculine love/lust, and not at all in her vision of a more egalitarian romantic love between men and women.��Is it possible for me to reconcile the fact that I know women are basically the same as men when you get down to it, just people, and the objectifying fantasies I have about them? Do I need to retool my sexuality entirely in order to make myself datable, let alone the good person I want to be in general?

-The Male Gaze

DEAR THE MALE GAZE: OK MG, I say this as someone who has written a LOT about toxic masculinity, the objectification and sexualization of women and trying to be a grown-ass man in the 21st century: put the bell hooks down and back away slowly.

Seriously my dude, you sound a 4channer trying to write a Male Feminist letter for s--ts and giggles. You are overthinking and overanalyzing to the point of absurdity, looking inward so hard that you basically turned yourself into a human klein bottle.

Here’s the thing: fantasies are just that: fantasies. Getting turned on by stuff, even the stuff that feels like “fire-bad-tree-pretty” caveman level of sexuality is fine. If you love some breasty women boobily boobing down the stairs in your fiction, that’s nobody’s business but you and your Amazon wish list. If movies and stories about dames with fishnet-clad legs that go on forever and curves like a stretch of bad road are what get your motor humming, then by all means, down a couple slugs of cheap rotgut and see what that femme fatale has to say for herself. Because hey, what turns you on is what turns you on. Nobody is expecting you to get cranked up over someone lounging around in an outfit that emphasizes her doctorate in theoretical physics or who accessorized her lingerie with the Fields Medal while reading Proust aloud and that’s fine. Nobody’s grading you on what you jerk it to.

Unless that’s what you’re looking for, anyway. I understand there’re folks on OnlyFans who’ll do that for you.

I hate to break it to you, my dude, but this isn’t exactly a deep dark secret that you’re carrying around. Having a thing for 70s era Playboy spreads or dodgy pulps with titles like Lesbian Librarians In Heat isn’t really going to shock or horrify anyone, any more than admitting that you visit PornHub. It’s pretty bog standard, honestly. Some might think it’s a bit immature if that’s all you consume, but getting a thrill from stuff that doesn’t have the Straw Feminist Seal Of Approval isn’t going to get you much worse than a roll of the eyes from anyone.

And really, that’s only if you go out of your way to tell them.

Part of what I think you’re missing is that the issue with a lot of the media you’re talking about is that for a long time, it was the only thing out there. The objectification and sexualization of everyone was constant, the minimization of women to sex-object was everywhere and it was treated as right and good and if you had a problem with it, then you were a scold and a frigid funwrecker.

But as society recognized that hey, the way we’ve been acting is kinda f--ked up and making everything about this very narrow vision of compulsory heterosexuality was even more f--ked up and we’ve broadened our horizons. There’s more material out there that aims to cater to a wider array of gazes, tastes and desires – from the chaste to the depraved, from the buttoned up to the jaw-drop-wolf-whistle-lip-bite and points in between… for all genders and sexualities.

It’s not like the point of the Bechdel Test or the Mako Mori test or the Sexy Lamp Test are markers of whether media is acceptable or not; after all, “Baby Got Back” passes the Bechdel Test. The whole point of them – as well as a host of media criticism about the marketing and selling of sexuality and masculinity – is to ask people to think a little about the media they’re making and consuming and remember that women are people too.

It’s also worth remembering that women, like men and enbies, aren’t just people, they’re also pieces of meat who occasionally want to be objectified. Not all the time, not by default and not by everyone, but it has its time and place and person. And sometimes that objectification is going to be happening strictly between your ears during some private time, and what goes on there is nobody’s business but yours.

Now, I suspect that the embarrassment and shame is part of the pleasure of it all. Shame and arousal are close cousins and there’re few things quite as arousing as the taboo. Feeling like what you’re doing makes you a naughty naughty boy may give everything an extra bit of spice. But honestly, nobody you meet who isn’t a Victorian time-traveler is going to be surprised that you get a semi for boobs and butts. Some might judge you, but honestly, most of what you describe is kind of basic. You’re hardly reading The Story of O, spanking it to Salo or touching yourself to 100 Days of Sodom, here.

And the Victorians, I might point out, were kinky as s--t behind closed doors. Some of the books that were published during the height of memetic prudery would make you pop your monocle.   

And hey, maybe it would do you some good to explore a little of what women read and watch to get turned on. The varieties of smut out there for women are wide and varied, and some of it is just f--kin’ weird. There’s a reason why monsterf--ker is a genre now. Fun fact: women tend to be more into tentacle porn than men.

The fact of the matter is that people fantasize, watch, read and masturbate to things that they would never do in real life, even things that would seem antithetical to their lived values. Because it’s not something they want to do in the real world, it just happens to be a thing that turns them on and gets them off. They just compartmentalize and recognize that fantasies are just that: fantasies. In phantasia veritas, except sometimes the truth is just “yeah, it makes me orgasm extra hard.”   

Now the bigger question would be: the more objectifying stuff is what you jerk it to, but how are you treating the women in your life? Are you doing your best to be as equitable as possible and behaving as though the women you interact with as human beings? If you’re not acting as though women are sexual objects who are just there to be consumed, I think you’re going to be ok.  Because, quite frankly, that’s going to mean a lot more to your friends and potential future partners than what’s in your spank-bank.

Feel free to keep on enjoying some Russ Meyer films. Just, y’know. Don’t make ‘em your whole personality.

Good luck.

Please send your questions to Dr. NerdLove at his website (www.doctornerdlove.com/contact); or to his email, doc@doctornerdlove.com