DEAR DR. NERDLOVE: I am a little bit unsure about an experience I had recently. 

Just some context. I am a nineteen year old man on the autism spectrum, high functioning. I had just completed a contract with $CARNIVAL as a ride operator. During my time as a ride operator, I was living in Burnsville to help with transportation, I normally live in Saint Paul. Now because of how hard that job was (It was not uncommon for me to work shifts that were over 12 hours long), I was feeling a very strong urge to party like crazy to blow off some pent up steam, so I did the smart thing and blew some money at Mystic Lake Casino at the Blackjack table. For your purposes, before this I have had no sexual experience, not even a kiss.

Now here is were it gets relevant for you good Doctor. I spent Sunday night after my contract ended at a Minneapolis strip club. I spent time (and hundreds of dollars) on some full contact dances with a stripper, who I may have crossed the line with or not (in terms of club rules, that is; all of the activity was consensual). The stripper, after I gave her money for full contact for a half hour, gave me permission to kiss her anywhere except her lips. So I began to kiss her all over, first her breasts then I worked my way down to her vagina. After I used my mouth on her a little bit, I fingered her a bit. In turn, after coughing up some more money, she began to rub my penis a little bit. I know I seem to have a lot of trouble just getting to the point but that’s also because of the fact that I had the feelings of “what the hell just happened” in a regretful voice in my head and also the feeling of “I just spent an obscene amount of money.” 

Now before you tell me this, I am aware of the fact the stripper who I spent a lot of money on probably hated me, or at the very least thought quite poorly of my judgement. I am also, logically and intellectually, aware of the fact that strippers are very good at faking emotions and that they are experts at getting money very fast. My main question is what the hell happened between me and this stripper. Sorry if I sound confused. Even though I am autistic, I know how to function quite well in an academic and work environment. 

So what the Hell happened?

Sincerely, Confused Man.

DEAR CONFUSED MAN: Here’s what happened, CM: you paid a dancer for a series of high-mileage lap dances.

Dancers, like everyone else, are going to have their own boundaries and willingness to allow physical contact beyond what’s allowed by the club (or the law). Some dancers will allow for more physical contact, especially if it means that the person in question will stick around and get more dances. A lot of dudes are more likely to want to buy more dances from someone if it means that they can get a hand full of boobs for the length of a Kanye song. Many dancers will use the suggestion (or guarantee) that even more activities may be on the menu as a way to up-sell a series of dances, a more private booth or access to the VIP room… because you’ll have more privacy, of course. On occasion, you may even come across a dancer who will do some escorting outside the club or play within the club, and do things like give a client a hand-job for an extra tip. This is – needless to say – not legal and most clubs have very specific rules about whose hands (and other bits) are allowed to go where. Some clubs are extremely vigorous in enforcing their rules, others will turn a blind eye as long as things are discrete (or the bouncer/owner are getting a cut) and there are some that are brothels in all but name.

Now as for the dancer’s feelings towards you: I doubt that she hated you or thought badly of you. Most dancers aren’t predisposed to letting someone they hate lick their nipples or let their hands slide into otherwise forbidden territory, no matter how much money the client may have. Without knowing the woman in question, I’d guess this was more of a client/provider relationship: you paid your money and got your experience, as it were. To her, this was just another day on the job. Maybe she didn’t like you much as a person, maybe she did, but it’s functionally the same as the barista that serves you your coffee or the waitstaff that brings you your meals. Sometimes the waiter thinks you’re cool, other times they wish they’d just eat your food and go.

Again, without knowing the woman in question, I couldn’t say. Some dancers have a fond relationship with their clients (especially their regulars), while others see the customers as ATMs with legs.

Now that being said: as with any service industry, there is a Professional Sexiness/Friendliness aspect in play: flirting and friendliness (or in your case, being VERY friendly) tends to mean more money for them. It’s in their financial best interest to get their customers to like them. Remember this the next time you (that is: guys who go to strip clubs) think the stripper may really like you. She might or it might be business or even both… but the odds are better that it’s business.

Lots of people end up blowing more money than they intended in the strip club. A hard d

k tends to correlate with riskier behavior and dubious decision-making, after all. The only question that remains is: do YOU feel the experience was worth what you paid? If so, then more power to you; that was money well spent. If not, then you’ve learned a valuable lesson: don’t make decisions involving money when naked women are involved.

DEAR DR. NERDLOVE: My boyfriend broke up with me out of the blue three weeks ago. He is going through some emotional stuff and has PTSD, and said that he still wants to see me but no longer wants any labels. He says he loves me and wants a future with me. We have been spending a lot of time together and when we are together it feels as though nothing has changed. He still kisses me and tells me that he loves me every day. However, he is now constantly messaging other girls and has taken down all pictures of us off social media.

We have so many similar interests and I’m completely in love with him. He is the one for me. He says that he needs about 2 months of not being in a relationship but still wants to see me. What does this mean? I don’t want to lose him or for him to lose love and interest in me? Please give me some advice!

Thank you,

Heartbroken and Lost

DEAR HEARTBROKEN AND LOST: I hate to tell you this, HaL, but what he’s telling you is that he wants to – and is actively seeking to – sleep with other women. “No labels” almost always means “no monogamy” as well.

Now, in fairness, some people are bad at asking to open up the relationship and may phrase it like this. But to be blunt: I don’t think your boyfriend is one of them. I suspect that this is a precursor to a REAL break up - one where he’s not still coming around for companionship and make-outs - once he finds someone else.

His behavior – taking down evidence of your relationship from social media while still being lovey-dovey with you – suggests that what he wants is to keep you around as a guaranteed lay while he’s out dating other women. Hiding the evidence of your existence and your relationship means that other women will see him as a free agent and he doesn’t look like a cheating piece of s

t. Meanwhile, by keeping things in this nebulous “no labels” territory, he keeps you on the line WHILE he’s checking out other women. By dangling the possibility of getting back together – the two month “trial separation”, the affection and declarations of love, etc – he keeps YOU from going out and dating other guys. That way, he always has someone to come back to if he isn’t as successful as he’d like to be.

In short: I think you’re his back-up plan and you deserve better than to be treated as the consolation prize for his junk. You can have a long and very blunt conversation about what he thinks is going on and explaining how you feel… but I think all that’s going to do is lead to a lot of bulls

t about how this is just a temporary thing and he’ll be back, etc.

I realize you may love him, but if he’s treating you like this, it speaks volumes to how little he respects you. Honestly, I’d suggest that you take this as a break-up rather than “a break” and leave his ass.

If he does come back, then you can decide whether you’re willing to take him back. But absent some serious mea culpas and making amends on his part, I wouldn’t recommend it.

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’m a straight male, and I don’t have a lot of relationship experience: only two girlfriends in high school, and neither lasted much longer than one month. In both cases I fell madly in love and didn’t realize it until weeks/months after they’d broken up with me. The thing I learned about myself through all the ensuing depression/self-loathing/suicide attempts is that I get hella attached, fall hard, and then take for freaking ever (years) to move on with my life.

Fast forward nearly 6 years and I’ve gone all throughout college without having one single date or substantial crush. This made it easier to dismiss my earlier post-breakup insanity as having its roots in adolescence, but I didn’t have the early-twenties relationship experience to test that theory for sure. Until now… Long story short, about a year and a half ago I met a girl online (long-distance) and proceeded to fall madly in love with her as well, despite the fact that we’ve still never even met in person. Well, things aren’t looking good right now and, SURPRISE! I find myself back in the same serious depression I was in before.

I won’t bother you with the intricacies of this particular long-distance shit show. The most interesting thing about it is that it’s led me to discover that I haven’t, for lack of a better word, “matured” at all as a romantic partner since high school: Reoccurring heartbreak aside, when I’m actually IN relationships I’ve always been the needy partner who cares more about my girlfriends than they do me. I’ve always been the one dumped, never the one who facilitates the break up or ceases to show interest and effort. I’ve always found something noble in the idea of sacrificial love: devoting myself to a person so fully that I always sabotage the relationship and risk sabotaging myself. I still find meaning in giving myself over to someone, even if they don’t appreciate me that much during the course of the relationship or know I still love them months and years after its over. I’m also realizing that I am now and always have been the most sensitive and nostalgic person I know, a professional-level crier, riddled with insecurities, clearly still a depressive, and kind of a hoarder (emotionally and otherwise. Recently, Long-Distance Girl told me I’m controlling, and I suspect my OCD has something to do with that as well.)

My friends who have more relationship experience than I tell me that the idea is to find someone who makes you the best version of yourself, but I seem to only have 2 modes: “Normal Chill Yet Empty Inside Me,” and “Obsessively Hopelessly In Love Me.” A change in girl has never yet changed that paradigm. Plus I think even if I found a girl I wasn’t so obsessive and self destructive about, that would just mean, comparatively speaking, that I wasn’t as invested in the relationship; and why would I want that if I know I can love so much deeper?

So Doc, my questions are: is this the kind of thing people eventually grow out of? And if so will it come with age, or only though more relationship experience? And if the latter, isn’t that a Catch-22?

OR

Should I just resign myself to the fact that this is the kind of lover I am, and only look for girls who are likewise needy and very, very devoted?

Thanks for the work you do,

Obsessively Hopelessly In Love Me

DEAR OBSESSIVELY HOPELESSLY IN LOVE ME: OK, keeping in mind that Dr. NerdLove is NOT really a doctor… I don’t think your OCD has anything to do with this. I think the problem is that you have low self-esteem and some emotional issues and you set yourself up for failure with relationships. This behavior isn’t terribly uncommon when it comes to people with depression, f’rex; we tend to be desperate for love and believe that we’re completely unworthy of it. As a result, we tend to become incredibly needy while engaging in behavior that intellectually we know is going to kill any relationship we’re in deader than disco.

It’s a messed up way of having your cake and eating it too except in this case it’s craving cake and flinging it across the room because we may want it but we don’t deserve it because we’re worthless and don’t deserve a delicious cake and I’ve kind of lost track of where I was going with this metaphor.

The point being is that the behavior you’re engaging in is fairly classic; you’re prioritizing somebody else’s approval and affection for you that you throw yourself at them like a lovesick puppy and calling it “love”. Except that’s not love. That’s desperation and it’s actually incredibly selfish. You’re not devoting yourself to somebody, you’re trying to make them love you by doing everything for them and making everything about your relationship with them.

Because, honestly? There’s nothing inherently noble or even romantic about “loving” somebody to the point of self-harm or self-destruction. Not only do people — people who’re worth dating, at least — NOT want their lovers to blow up their lives for them, but it’s not like you’re even doing it for THEM. You’re doing it for YOU; by making such a production out of what you’d do for them, you’re trying to create an obligation towards you. “Look at everything I do for you, how can you NOT love me back?”

I’d suspect – especially if you’re anything like me when my depression was at its worst – that when you’re in your “hopelessly in love” state, you’re always wanting to talk to them for hours, always doing things for them, always worried that you’ve said the wrong thing and wanting to spend every single waking moment with them. When you’re with them, I’d imagine you’re incredibly physically affectionate, always wanting to hold hands or keep your arm around them or kiss or what-have-you.

That may feel like you’re being a devoted, affectionate boyfriend. But to everyone else – especially your girlfriends –this is incredibly smothering. You’re continually asking for reassurance, clinging to them as though you’re worried that she might get away and always afraid that if she talks to somebody else, she might leave you for them. A lot of the behavior you think is sacrificial and devoted is really demanding that she take responsibility for your emotional well-being and that’s a hell of a lot to ask of a partner, especially a new relationship.

(Did I mention that I used to be exactly like this? Because I did.)

Part of the problem is that you’ve romanticized your issues. The fact that you throw yourself completely into them isn’t proof that you love them deeper. It’s a sign that you don’t feel like you have value in and of yourself outside of what you do for others. You’re not winning people over with the strength of your love, you’re showing them that you’re incredibly insecure and demanding their constant attention and reassurance. Your friends are right: the best partners are the ones who inspire you to be the best version of yourself, just as you bring out the best in them. It’s a relationship of mutual respect and self-respect.

I think what you need, more than anything else, is to talk to a therapist and getting yourself emotionally healthy. Those issues you mention – the depressive moments, the insecurities and mood swings – are things that you should be working on before you try to date. You don’t need to be in perfect emotional shape to date, but you should be in good working order… and right now, you’re not. Spend some time getting straightened out, and I suspect you’ll find that you have fewer and fewer issues with being overly clingy with future girlfriends.

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 have re-written this letter a thousand times in my head and am still not sure it is one of the things that registers in the NerdLove realm, yet I feel you might be the only one who can help me with this… well, I hesitate to call it a problem as much as an unyielding curiosity.

Let me just begin by saying for my entire life I have dated in the hetero-realms. I got off to a slow start and hit a bullet train in the vis-a-vis dating world around late high school, with another acceleration happening in college. There are tons of stories there that I’d love to flesh out, but I’ll leave them for the sake of getting right to the point.

I am in a new city and am rediscovering myself as it pertains to finding friends, enjoying the hobbies I am into, etc. I hesitate to say it is going super well but it is going which I am perfectly happy with. My question is simple, and yet kind of touch and go and crazy and god knows what else: I have recently discovered that I have a very real desire to date and or sleep with trans women.

To be frank and clear, I am not attracted to dudes at all. That said, I am however finding that I could be VERY interested in being with a woman who… well, had a significant dude-part (as it were). Now, all of this is quite speculative. I have never been penetrated (pegging, etc whatever you want to call it) but I am very interested in the concept. I should also probably add that I have been single for quite some time and am by no means just swimming in dates that I could potentially attempt to vet with aggressively invasive questions a la “do you have a penis and, if no, do you own a strap on?”

My initial thought is that one would assert the sex positive aspect of this. While I don’t find this desire odd or weird at all, I am just not certain how to approach it. Where do you go or hangout to meet people? In what way do you express your lack of experience in combination with wanting to desperately give things a shot?

I must say that for all my social skills I am not sure how to approach this one. I have an easy enough time talking to women (though I do have to work on the whole “she is sending signals and you should get her number/ask her out” thing) but I feel like this is a multi-tiered dilemma. Any and all love of the nerd persuasion to this situation would be appreciated.

Sincerely,

Seeking Something Different

DEAR SEEKING SOMETHING DIFFERENT: Whoo boy.

Ok, SSD, this is an area where it’s best to proceed carefully, because it’s very easy to end up making someone feel dehumanized even when you’re trying to express genuine interest in them.

Let me start with the less-obvious point, StWP: being interested in trans women doesn’t make you gay or bi. Trans women are women, period. Similarly, being interested in butt-play, prostate stimulation or other forms of penetrative sex beyond penis-in-vagina, whether giving or receiving, has nothing to do with your sexual orientation; it just means you’re discovering that you’re a little less vanilla or conservative than you realized you were.

Hell, even just wanting to play around with gender roles or doesn’t mean that you’re not straight. It just means that you’re more flexible than other folks.

And hey, that’s awesome. No matter what the reason is for your newfound interest, let your freak flag fly high and proud and follow the best-practices as outlined by guides like Erika Men and Mathew Nolan’s “Oh Joy Sex Toy” or “The Ultimate Guide to Prostate Pleasure” by Charlie Glickman and Aislinn Emirzian.

Now, with that out of the way, let’s get to the part that makes me pause. It’s cool that you’re interested in trans women… but the way you’re framing your interest gets a little tricky. It sounds to me like you’re fetishizing and exoticisizing them, which ain’t cool. 

While there’re definitely trans women who’ll appreciate a man who’s into them because they’re trans – after all, people aren’t just people, we’re all also pieces of meat, and there are times when it’s nice to know that someone wants you specifically for what makes you unique – but there’s a fine like between digging someone for who they are as a person and being reduced to just one aspect of themselves. As long as everyone else involved is on the same page with what’s going on, that’s cool; blessings on you both. But you need to be mindful of the fact that what for you is a kink or a little exciting bit of spice, is someone else’s life.

The last thing most people want is to be a prop for somebody who fancies themselves experimentation with being edgy and transgressive. A trans woman being made to feel like they’re just “a chick with a d

k” who’s there to provide naughty thrills somebody looking for a walk on the wild side is feel incredibly dehumanize and that’s an awful thing to do to someone.

(Unless of course, that’s their particular kink or they’re a sex-worker providing a service. But I wouldn’t bet the rent on it.)

I’m not saying that you can’t or shouldn’t date or sleep with a woman who’s trans, but I am saying that you need to tread incredibly carefully. There’re a lot of potential minefields that you want to avoid, both for your sake and hers.

You’re also assuming that trans women are going to be interested in being the penetrator by default. That ain’t necessarily the case. If what you’re looking for is being pegged by a woman, specifically, you may have better luck looking for a cis woman who’s into bending guys over.

So that being said, your best bet for finding someone is going to be online. After all, you want something fairly specific, and this is one of the times when it’s better for the mountain to come to Mohammad instead of the other way around. If you’re looking for someone who’s packing a strap-on and an urge to use it, you want to go where the kinksters hang out. FetLife and other kink-friendly dating sites are an obvious place to find women who’ve got an interest in pegging. Create an account, get to know folks in your area and see if you can find someone who’s interested in topping a guy who’s curious about being pegged.

You can also browse around on OKCupid, looking for people who’ve answered specific questions or checking for particular keywords. It should be noted that it will take some digging and reading between the lines to find women who might be interested pegging a man; most women who indicate an interest non-standard sex tend to get deluged with so many creepy messages that they tend to fold up shop or go incognito. You may have to create a profile specific to your interests and wait for THEM to find YOU.

But you’re going to need to be very clear about what it is that you want and are looking for. If all you’re doing is looking for a specific experience, then you don’t want to be giving people the impression that you’re looking for a relationship. Giving people the option of opting in will be far better for you - and them - then using the veneer of dating to find the sexual experience you’re after.

You may be better off looking for people who’re willing to provide that exact experience, rather than casting about at random and hoping to find someone who’s either trans and/or into pegging and end up treating them less as a person and more as a means to fulfilling your fantasy.

Good luck.

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