DEAR DR. NERDLOVE: I wonder if you can write on the topic of getting over women’s sexual histories, especially when they’ve gone through long hook-up/casual dating periods and a man has not. Or maybe about guys who’re plagued by feelings of not measuring up in experience, number of partners, degrees of wildness, etc. I think many of your readers will be going through this as well, dealing with feelings of insecurity and perhaps craving some of the wild things or numbers of partners they hear of friends doing, hear of their dates or girlfriends doing, but none of which has ever been extended to them.

Obviously this is largely a personal request–I had a potential partner I was interested in tell me she’s been through a hook-up phase, had threesomes with previous boyfriends, but wouldn’t be doing any of that again. I didn’t press her on it, but it killed me to hear that, immediately and irrationally made me feel it’s about me. It made me feel like I’m not interesting or cool enough or exciting enough for her to be a bit wild with me, now that she’s had here YOLO moments. I think I’m really, maybe obsessively, struggling with thoughts of the ease with which many women can go wild if they so choose (I know that’s not the case for every or even most women, but it seems the case for those I’m attracted to). I am craving some wild experiences myself, if only so I no longer feel threatened by women who have had them and can graduate from feeling upset when I hear or suspect a woman I am interested in partook of orgies or something. For what it’s worth, I live in a major city where this kind of stuff is anecdotally not uncommon. Maybe I should be reading guides to make it happen for myself rather than tell myself I need to suppress these desires, though they are probably born of YOLO/FOMO, New York Times articles about orgies in NYC, porn, and a desire to make up for my entire 20s spent in depression despite having everything seemingly going for me.

Whatever thoughts you might share or write would be greatly appreciated.

Missing Out

DEAR MISSING OUT: As it happens, I have written quite a bit about getting over people’s sexual histories, and you can find them via my archives. This is an incredibly common issue that comes up a lot, especially for men who date women. This tends to come in two flavors: the guys who feel disgusted that their girlfriends and wives have had such an extensive sexual history, and guys like you, who feel like they’re somehow being “left out” when they find out that their partner isn’t as wild or sexually active as she used to be.

As tempting as it is to just say “get over it”, it’s useful to examine just why these scenarios tend to cause such anxiety, particularly in men. At their core, the chief issue is one of anxiety and insecurity, particularly in the less-experienced partner. In the former, men get obsessed with the idea of their partner’s “purity”, equating women’s value with how much sex she doesn’t have. When it turns out that the woman in question has a sexual past, guys get hit with waves of anger or revulsion… not because there’s anything wrong with the women, but because of how it strikes at men’s own sense of value and importance. For a lot of men, especially ones of a more conservative bent, the idea that women don’t like sex or that it’s difficult to get women to sleep with you is important; it means that you’re just that special or virile. You’re somehow demonstrating your superior value by doing what other men couldn’t: seducing this woman into being sexual with you. If, as it turns out, she likes sex and is confident in her own sexuality… well, now you’re not as special, are you? Worse, now you’re functionally “competing” with others. If she was inexperienced — or better yet, a virgin — then (in theory) you are by default the best lover she’s ever had. After all, she has no basis for comparison, does she?

(This, of course, ignores things like the fact that bad sex doesn’t magically become good just because you’ve never had anything to compare it to. Someone who eats a sh

ty sandwich isn’t going to decide it’s delicious just because they’ve never had a sandwich before; they’re just going to avoid eating sandwiches in the future.)

But rather than examine those feelings and recognize the insecurity for what it is, those guys put the blame on their partners.

On the other hand, we have the folks who, like you, feel left out when they find out that their partners have had sexual experiences that they themselves haven’t. For a lot of guys, this leaves them feeling unworthy or lesser; why would those other guys get to share these experiences with her while they don’t get to? What do those men who came before have that makes them so much more deserving of wild sexy adventures while the less-experienced are left behind?

The problem in this case is that more often than not, these guys are asking the wrong question. As I’m often saying: women aren’t Mjolnir; whether they have sex with someone or not (or what kind of sex they have with them) isn’t a measure about whether that person is worthy or not. Instead, the better question to ask is how their partners felt about those sexual experiences… and, more importantly, why they’ve chosen to stop having them. If you were to ask, you might find out that the reason why women had those particular experiences had less to do with them and more about their former partners. They may have been dating people who insisted that they take part in sexual activity that they may or may not have been interested in themselves and felt like they had no choice but to participate. Lots of women have had partners who made demands of them, coercing or pressuring them into doing things that they wouldn’t have chosen to do on their own. Other times, they may do something they weren’t into just because their partner was and they wanted to make them happy, and they felt that this particular activity wasn’t so far outside of their comfort zone that they couldn’t bring themselves to do it.

Alternately, they may have decided to stop because they had a bad experience, or enough bad experiences that made them decide that it continuing just wasn’t worth it, even if they dug most of their adventures.

Still other times, women — like many men do — may go through periods of having wild crazy sex because they feel like it’s something they’re supposed to want. Or they may do it because they’re curious and discover that they didn’t like it that much after all. And of course, there’re plenty of people out there who will have a particular type of sex or sexual expression because of other issues in their lives. A good friend of mine was a submissive, not because that was her natural orientation but because of emotional issues that she had been facing; bad experiences left her feeling as though submissive behavior was how she “earned” or “deserved” people’s love and attention. Once she started confronting those issues, she began to realize just how different her actual sexual orientation was.

And like I said: women aren’t the only people who go through this. Plenty of men will adopt a performative sense of sexuality because they feel like it’s something they’re supposed to do. I’ve coached plenty of clients who thought they were supposed to want one-night stands and casual sex and couldn’t understand why it left them feeling empty and unfulfilled. Others couldn’t understand why they struggled with monogamy when society had taught them that desiring someone besides your partner meant that there was something wrong with you.

Now in your case, Missing Out, there’re few things at play. The first is that you need to decouple how your sexual experience — or lack thereof — from your sense of worth. Whether you’ve had the kind of sexy escapades that would make Caligula blush or you’ve mostly had fairly standard meat-and-potatoes sex is completely and utterly irrelevant to your worth or value as a man. The fact that other people may have had experiences you haven’t doesn’t make them better or more admirable than you; it just means that they’re different people who’ve had different experiences. Some people will go their entire lives without having caviar or a cronut or bibimbap. That doesn’t make them less than folks who have had it, it’s just food they’ve never eaten. Their lives are no less rich or fulfilling for the lack.

You also need to recognize that the craziness you think you’re missing isn’t as common as you think it is. Part of the reason why you’ll occasionally see stories in newspapers and why they stand out on blogs or Twitter or what-have-you is because they’re outré. They stand out because they’re not common; we don’t devote column inches to things that are daily experiences for folks. It’s not as though there’re tons of articles being written about people, say, tailgating before football games. And porn is to real sex as the Fast and the Furious movies are to driving; it’s over-the-top fantasy, not reality. Being upset that you’re not f

king like Ron Jeremy is like being upset that you don’t drive like Dominic Toretto.

But just as importantly, there’s nothing wrong with wanting those experiences. There’s absolutely nothing wrong with wanting to have threesomes or have public sex or sex in group situations. This isn’t something you need to suppress, it’s something you should understand and accept as just being part of who you are. But in doing so, you have to recognize these desires as part of what will make someone sexually compatible or incompatible with you. This means that when you’re considering a potential partner, you’ll want to consider their sexual interests too. If they’re someone who isn’t interested in the kinds of sex you are — or who are at least open to trying it, within reason — then the two of you simply aren’t right for one another, and you’d be happier in the long run to find someone who is compatible with you.

However, one of the things you need to keep in mind is that very few couples have that kind of wild crazy sex right from the jump. Sex requires trust and communication, and the more outre the experience, the more trust and communication you need to have. Couples very rarely go looking for special guest stars or hitting swingers parties without having a strong foundation first… and that foundation is built over time. So while you can get there, it may take time, even with a partner who’s down to get wild.

And part of that process is finding out how your partner feels about things, especially if she already has a history of sexual adventure. If we go back to the potential partner who decided that she was done having wild sex, you would want to recognize that her decision that she was done having those sexual experiences almost certainly had nothing to do with you and everything to do with her. It would’ve been better to ask her about why she was done. If you can listen — really listen, without making her feel judged — then you might have found out more about her and where she is in her life. She might have been up for trying some of those things again with the right partner. Or you might have learned that she was absolutely, totally done, period, the end… in which case, it would be better for both of you to find people who want the same things.

And one more thing to keep in mind: there’s really no such thing as “making up for lost time”. You may have been dealing with depression in your 20s, but that doesn’t mean that you’ve somehow missed your window for sexy adventures. There’s a reason why, if you go to swingers events or sex clubs, you’ll see that most of the people there are in their 30s and 40s. We may romanticize the young, but sex doesn’t end once the clock ticks to midnight on your 30th birthday. People have wild, awesome sex at all ages. You don’t need to “make up for lost time”, you just have to live your life now, in the present, instead of getting lost in a past that might have been.

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 am not your “typical nerd girl” as per the men at the comic book shop I frequent, which is obviously, bs. I’m also newly (1 year ) single after seven years from my uni boyfriend who was also not your “typical nerd” despite both of us loving comics, cosplay, anime, sci-fi, D&D and video games, we also loved sports, I studied fashion and went to the gym.

Now, I don’t want to be back with my ex and this isn’t about this. This is background to say I have never dealt with quieter, more nerd stereotype men before-that I am interested in and would like to date.

There is a man I am interested in at work (large business, different departments, no one supervises each other and relationships are okay), who has never been my type, physically. I think he’s super cute, and the fact that he wears suits to a laid back office, is great. The issue is I don’t know if he’s interested in me.

We worked together on a project, a few months ago. We have a lot in common, books, movies, D&D, etc but he’s quieter, more introverted and shyer that I’m used to. I’m also not used to not knowing if someone wants me. I know he’s single, I know he got divorced two years ago (so he obviously knows how dating works), and there is a bit of an age gap (I’m 27, he’s 32) and he keeps on doing things that almost seem like he’s interested but not quite.

He started showing up to work baseball-something I love, and he hates sports. I was streaming the NBA finals while we had a meeting and he decided to read because the rest of us weren’t getting work done. He’s brought me coffee twice, but he brings his entire team coffee, and sometimes other people.

He’s asked me what I’m doing Friday night, when I said I have no plans, he says okay and then changes the conversation. He remembers and asks me about things I’ve mentioned months ago; for example, I love Audrey Hepburn movies so he would tell me that some Youtuber did a review about Charade.

All of this points to being interested, but when I low ball openings “Hey I owe you coffee next time, when’s a good time”, he brushes me off. “Hey, wanna grab drinks after baseball with me and so-and-so” he’s busy.

It feels like he’s interested, but it also feels like he’s just being nice. I’m trying to use my words, but because we work together-even tangentially, it’s hard to be as direct as possible without rocking the boat.

So advice, help? I’m not used to trying to guess if someone is into me or not?

Reading the Tea Leaves

DEAR READING THE TEA LEAVES: Here’s the problem a lot of folks have with trying to gauge interest: there is rarely a point where you will know with 100% certainty whether someone is into you or not. Even at times when it feels like someone is all but screaming “TAKE ME! TAKE ME NOW YOU RAVISHING SUCCUBUS”, it’s entirely possible that this is just how they are with everyone.

This is going to be doubly true with men in a work environment. While I’m the first to say that no, the #metoo movement did NOT ruin flirting, folks are a lot more conscious about the dynamics of dating and flirting while on the job. As a result, some people are going to be doubly and triply cautious about not wanting to make women uncomfortable or come off as the office creeper. So it could well be that he’s interested but afraid to take things forward in case you aren’t interested.

But by the same token: he may just be friendly. Some guys are good at remembering what folks are into; his telling you about the YouTuber doing a deep dive on Hepburn movies may have been  a case of seeing something and realizing “Oh hey Reading The Tea Leaves might dig this”.

Alternately, he might be gun-shy; even after two years, a divorce can throw folks for a loop. He may legitimately be interested, but not be in a place where he feels like he can date yet. Or he’s just so shy and introverted that he didn’t recognize an invitation when you lobbed it low and slow over the plate.

But at the end of the day, there’s only one way to know if he’s into you as a potential date: ask him out on one. Since he seems to be missing the clues you’ve been sending — and in fairness “grab drinks with me and other person” doesn’t sound like the lead-up to a date — if you want a date with him, you’re going to have to be blunt. That means making it clear that you’re asking him out on an unambiguous date. Not “to hang out some time”, not “get together”, but a date. Use the word; say “Hey, I really enjoy talking with you and I’d love to take you on a date some time. What does your weekend look like?”

It’s understandable that you’re afraid of rocking the boat at work, but being subtle isn’t working. If you want to make this happen, you’re going to have to be willing to risk the possibility that he may not be feeling it or that work could get a little awkward for a short time afterwards. But as I’m always telling men in your shoes: the key to avoiding the awkward is to not make it awkward. If you make it clear that it’s cool for him to say no, you take a “no” with grace and continue to treat him exactly as you had before you asked him out? It’s much easier for the two of you to power through the awkward and get back to being work buddies again.

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 was a lonely kid. I remember reading a story in 5th grade that described a friend as someone who you told your deepest secrets to, and felt mystified enough by that to mention it in this letter two decades later. Fell into some social circles by middle and high school, and fell right out of them again once those concluded. Dropped out of my first year away at college so hard it registered on seismometers. My bad breakup that year made me terrified of any negative feelings in a relationship – the moment the first hint of jealousy showed up after that, I would shut down completely.

After years of underemployment and living at home, I joined the Army. For two months prior to basic training I felt like a normal person. I was working out two hours a day with a small group of dedicated future soldiers and everything just clicked. I was well-liked by peers and superiors, and did well enough to make Staff Sergeant. However, despite being respected, I never really made lasting friendships, whether with co-workers or while pursuing my hobbies outside of work. Either I would invite people to do things and they would consistently flake out, or I would join people for social events outside of work and feel more distant than ever. I did go to a succession of therapists while I was in for (basically) dysthymia but never did seem to get anywhere.

Now I’m in a vocational program in a new city and between jobs. I’m going to meetups and pursuing my hobbies but the whole making friends thing still eludes me (as does a greater life purpose, but one problem at a time). I don’t think my social skills are bad – I can Dale Carnegie my way through most interactions. Active listening isn’t a problem because people usually are pretty interesting if you give them a chance to talk, and I do far more listening than talking. I just feel like real connection is consistently eluding me and I don’t know why. Obviously if I can’t make friendships then anything romantic is a non-starter. What few romantic relationship attempts I’ve had fizzled out when she lost interest.

I’m having a hard time visualizing what a close friendship would even look like, beyond showing up and doing things. I’ve been carefully curating what I say for so long that I don’t know how to be authentic in a relationship in a way that isn’t emotional vomit. Expressing how I actually feel has consistently had negative results; reaching out to others always left me feeling disconnected, so I stopped.

So in sweeping terms the answer seems to be vulnerability. However, I’ve read your material, as well as reading Brene Brown’s book and several other sources and where I’m arriving consistently is “yes, but how?” There’s some sort of underpants gnome logic here that I’m clearly missing.

Stuck in a Fishbowl

DEAR STUCK IN A FISHBOWL: Have you ever met someone, had a conversation with them, even worked with them for weeks or months and only belatedly realize that you know absolutely nothing about them, SiaF? You have some bare-bones basic knowledge of the facts of their lives — what they did over the weekend, how they feel about their current assignment at work, how they felt about the conclusion of the Skywalker saga… but you don’t know anything about them as a person?

How often would you think of that person when it came time to do something social? How often do you think about that person at all when they’re not in your immediate eye-line or required for some task that you’re working on? And how often would you consider that person anything more than just an acquaintance, another face in a sea of faces at work. Someone to nod at on the way in or as you’re leaving for the day, but that’s more or less it?

From the sounds of things, that’s what’s going on with you, SiaF. You can socialize, you can charm, you can mingle… but you don’t really connect because it doesn’t sound like you give anyone anything to connect to. And I suspect the problem is one of authenticity and vulnerability.

At the heart of the matter is the idea of vulnerability. This is something that a lot of folks get wrong, especially men, in no small part because we tend to see vulnerability as just letting down all the shields and feelings-vomit all over the place. Contrary to what we’re primed to expect — hey, we’re being vulnerable, people should respond to that! — what we get are folks shying away from us, particularly other men. Because we’re socialized to believe that the only acceptable emotions to display are anger and stoic indifference, we have a hard time expressing how we genuinely feel. We’re functionally out of practice and so we tend to just barf everything up like an emotional Mr. Creosote.  This isn’t productive under the best of circumstances, but it’s especially off-putting to other men. Since we’re not used to expressing emotions ourselves, we tend to uncomfortable with outward displays of emotion, especially any that we consider “weak” like sadness or frustration; doubly so if it involves tears.

(This, incidentally, is one of the reasons why so many guys think that women tearing up is “cheating” somehow; they’re so uncomfortable with such an open expression of emotion that they try to avoid it or make it stop.)

But being vulnerable isn’t about just feels-dumping on people or having no boundaries or filter. It’s not about just projectile-vomiting your feels all over the place or sharing whatever thought comes into your head, it’s about expressing yourself authentically. Take, for example, the concept of a “guilty pleasure”. The idea is that this is something that you enjoy that you know you’re not “supposed” to. It could be a manly-man’s love for Taylor Swift’s music, a grown-ass man enjoying cartoons like Steven Universe and She-Ra and the Princesses of Power, reading “trashy” books or other things that are somehow out of bounds for whatever reason. But defining things as a guilty pleasure is the exact opposite of vulnerability and authenticity; that “heh heh, yeah I know I’m not supposed to like this” is a way of guarding against judgement by acknowledging that he’s not supposed to enjoy it. Someone who’s letting themselves be vulnerable, however, isn’t going to make excuses; they like it because it speaks to them or because they enjoy it in and of itself and they don’t care if other folks think it’s weird.

Similarly, vulnerability is the opposite of the curated life that many of us live. In an era of Twitter, Instagram and Facebook, there’s this intense pressure to live a life that seems perfect and amazing at all times. Everything is posed, staged and airbrushed within an inch of its life because it’s being propped up for the consumption of others. We’re putting up emotional and social Potemkin villages in order to show the world just how awesome and amazing we are. But embracing vulnerability means not being afraid of letting the cracks show. It means letting go of the idea that you need to display excellence at all times. Not every weekend can be a crazy rager or an amazing adventure. Not every meal is going to be a banquet and not every paycheck is going to be a fortune. Sometimes your dinner is going to be scrounging crackers and cheese like a trash-goblin; sometimes your weekend is going to be spent on the couch because you were just overwhelmed and needed to turn your brain off.

When we embrace vulnerability, we are being emotionally honest. We’re letting people see our real selves. That lets us forge real connections with the people we’re looking to build relationships with.

Now like I said, that doesn’t mean that you just go up to someone and open up to them about how awful your weekend was. It’s more about not being afraid to let them see the real you and get to know you on a level that’s deeper than what’s on the immediate surface. You don’t need to tell them all about your insecurities or your deepest fears; you just let them see more of who you actually are and what you’re actually about.

And yeah, you’re probably going to have to be the first to be vulnerable with folks. Many times, connecting with people and making lasting friendships means modelling the kind of friendship you want to have. That’s why the key is being real with folks; by doing so, you’re giving them permission to be real with you.

You’re also not just sitting around talking about your feelings (but hey, you can totally do that too); you can be real and bond while you’re doing other things. You can grab beers and talk about real s

t. You can play video games and still talk about goals or ambitions and interests. When you have those moments to talk about something real or meaningful about you, let yourself be real instead of going with the expected, humorous or otherwise defensive answer.

The more folks you’re spending time with feel like they’re getting to know the real you, the easier it becomes to forge a connection that’s more than just weak, surface ties.

Good luck.

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