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)

DEAR DR. NERDLOVE: I’ve got a communication situation that I’m hoping you can give me some advice on. I’m poly, happily married and have been dating my boyfriend for three months. My boyfriend is sweet, smart, cute and we have a lot of fun together. I feel comfortable and safe when I’m with him (which does not happen with people often for me). As a part of being together, he’s also been really beneficial to me by naturally being someone who seeks variety in activities - he’s introduced me to indoor rock climbing, wants to try trapeze, etc. I have a tendency to settle in a rut so being with him challenges me to go out and try new things and step outside of the comfort zone I’ve built around myself. I very much appreciate that about him (and have told him so).

Thing is, he doesn’t seem to have much emotional intelligence, in the way of having self-awareness of what he says and does and how it impacts people. I understand that it comes from a place of being clueless rather than being intentionally mean - I have a lifetime of dealing with a dad and sister the exact same way. I also know, though, from that life experience that my being an emotion centered person can sometimes cause hurt feelings on my end during interactions and my strategy so far in dealing with this type of personality has been either to try to calmly call them on mistakes or let stuff go.

I’m naturally a word person (written page better than spoken) and my boyfriend can often say things or use words that leave me confused or going “WTH?” For example, upon introducing me to his dad and stepmom, he told them that he had “acquired” a girlfriend. His dad questioned him on using “acquired” and mentioned that I was a person, not a piece of furniture that my boyfriend bought. I said I agreed. His response was that he figured it was understood what he meant.

I heard through the friend grapevine that his last relationship ended largely because of his lack of awareness of the impact of what he was saying, though I don’t know any details. I see his lack of emotional intelligence also manifesting in a lack of stepping up to responsibility in his house, leaving his roommates to take up the slack, and in how he can be very impulsive and not think of the bigger picture outside of himself. This week he has been very busy and so communication has been sporadic and initiated by me (we mainly talk via text and apps). At one point I said that that I missed talking with him. I also said that I understood he was busy, and looked forward to seeing him later this week. His response? “Thanks!” I get that he might not have understood that I was hoping for some positive words reciprocated (my roommate calls him Captain Clueless) and that instant messaging as a communication device is flawed, but it left me feeling sad. He doesn’t often say nice things to me; I think the biggest compliment he’s paid me so far was when I mentioned to him that he was important to me, he said “You are the person I’m currently the most comfortable with”. Though, so far he’s done what he said he would do and has been consistent in his actions, so that has to count more, right?

The thing is, when things like this happen it triggers the insecurities I have around being wanted and my mind takes the bad and runs with it- I question whether he cares, if I’m just convenient, if he’s starting to find me boring, etc . I’ve gotten better about reeling my mind back in but until I do and can counter myself with reality (that I can’t control anything, that he’ll either want to be with me or not and I’ll find out either way), I’m miserable. I do, however, realize that it’s my own crap and that it’s mine to deal with. I go to therapy, and over three years but most actively in the past year and a half I have been working on myself and confronting inner demons. Through poly dating I have encountered people who ghosted on me, played with my emotions, and used me as a life-sized sex toy (same stuff you get in the non-poly dating world, as well, I know). Dealing with each situation has been a painful but necessary lesson and I’ve grown as a result. I realize that the work I’m doing is a life-long process, but it still sucks.

I’m hesitant to say anything and ask for reassurance because I don’t want to come off as needy; I also don’t want to be asking for what he can’t give since that doesn’t seem fair. I also don’t want every conversation we have to include how he’s said something wrong. However, I’m questioning whether I chose the wrong person for a relationship, and if I matter to him. I’d greatly appreciate any insight you had as to how I can communicate with him better about what I need and any insight into how we can communicate better in general. I apologize for this being so long and thank you for your time.

Best,

Work in Progress

DEAR WORK IN PROGRESS: There’re more questions in here than I think you realize, WiP.

Let’s start with the obvious: trying to understand what’s going on in your boyfriend’s head when he says these things. Some people who tend to use the wrong words – such as “acquiring” a girlfriend – simply don’t have much in the way of a working vocabulary. They recognize words that kinda fit but they don’t necessarily get the context. It’s a little like trying to communicate in a foreign language; you know what you’re trying to get across, but occasionally you’ll end up using a word that’s hilariously (or uncomfortably) inappropriate. Getting corrected on this – especially by family – can be a little embarrassing. It could be that he’s the sort of person who’s brain runs faster than his mouth and by the time he’s said something, he’s run off to an entirely different train of thought and the rest of him has to play catch-up. Or it could be that he’s just really self-involved and doesn’t worry too much about little things like “how the way he communicates makes his girlfriend feel”.

(It’s also possible that he falls somewhere on the autism spectrum, but without an actual doctor’s diagnosis, it’s a little irresponsible to speculate).

The way that you describe his behavior makes me suspect that he’s the sort of person who’s off in his own little world and is rapidly running out of oxygen. He knows and appreciates the people around him (to an extent) but he’s so caught up in his own head that anything that doesn’t affect him directly and immediately, it tends to go in one ear and out the other. He tends to ignore things like, y’know, basic responsibilities around the house because something else popped up and sucked up all the available bandwidth in his brain.

(Speaking for myself, I’m especially prone to being distracted, which can lead to forgetting things like replying to emails, remembering appointments and paying bills. This is why I have redundant systems of truly annoying reminders on just about every electronic device I own to keep me on track.)

To the outside observer, it can seem like a callous disregard for others, but it’s frequently a case of Hanlon’s Razor: never assume malice when ignorance is equally as likely. It becomes a case of out of sight, out of mind; he may mean to do something right up until something else catches his attention.

Now that being said: understanding him doesn’t excuse him. Just because he’s focused on whatever inner world he has going doesn’t mean he gets a pass. The problem is he’s being a selfish prick; he’s drifting through life without being giving too much concern about anything outside of his immediate attention span.  You’re worried about asking him for what he can’t give, but it’s a question of “can’t” or “won’t“. Right now it seems like he’s been allowed to float through with other people more or less enabling him in his clueless self-absorption. When his roommates are willing to take up the slack as he ignores his share of responsibilities around the house then why the hell would he shape up?

Now the next question is: how do you handle this? Well, to start with: you’re a word person, s o use your words. I understand not wanting to come across as needy, but there’s being needy and then there’s asking for some basic consideration and care from someone who supposedly cares about you. You’ve got some insecurities and you want reassurances. That’s not a bad thing! It’d be one thing if you were expecting one (or two or more) people to carry all of your emotional baggage for you, but that’s not what you’re looking for. You’re simply asking for him to, y’know, communicate with you a little. That’s a reasonable ask.

So explain to him how you’re feeling. If you’re better with the written word than in person or over the phone, then write it all down in an email. Let him know that you’ve got some concerns about how things are going and you want to make him aware of what’s going on and how it’s making you feel. Focus on the way things affect you rather than “there is a right way and a wrong way to do this”. Explain about occasionally you have these insecurities and certain behaviors can cause them to flare up and you’d appreciate his help and reassurances when it happens. Treat this less as a “here’s what you’re doing wrong” missive and more about “how do we fix this“. Then tell him over IM that you’re sending him this email and you want him to let you know when he’s read it.

(Incidentally, I know it’s your boyfriend who’s triggering these insecurities in you, but I hope you’re confiding in your husband as well and he’s helping provide you with emotional support and reassurance.)

How he responds to this will answer the remaining question of “is he the wrong person for a relationship”. Focus less on his words and more on his behavior. Anyone can say they’re sorry; is he making a good-faith effort to repair things, or is he doing the bare-minimum until something catches his attention and he forgets? Is he being on his best behavior until he figures he’s in the clear, or is he legitimately trying to better?

It’s ok if he’s doing things imperfectly, but he’s making a genuine effort to improve; you’re not going to correct behavior, especially long-held behavioral habits, in a day or a week. But if every conversation is about how he’s said something wrong (or isn’t saying anything at all), that’s may well be a sign that he’s not trying. It’s one thing if he struggles to improve. It’s another if his behavior suggests that he doesn’t care.

And if he doesn’t… well, then you’ve got your answer: no, he’s not the right person for this relationship.

Good luck.

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