DEAR DR. NERDLOVE: I’m a 23 year old man, whom has suffered chronic general and social anxiety, three bouts of major depression, and years of constant bullying. I also have some (okay, lots) of issues with perfectionism and negative self talk, though I’m actively working on those. But for all that, I made good grades, earned scholarships, and just graduated with my bachelor’s degree.

The last eight months have been some of the happiest of my life, even during what was the most stressful year of my college career. Why? After years of rejection, bitterness, more rejection, self loathing, and finally despair, I found a girl. Rather, she found me, on a site I had given up on. We started talking, and we have so much in common. We understand each other’s humor, and also each other’s baggage. It’s even been worth going long distance, though we really only get to see each other about every two weeks, since she still has several years of higher ed ahead of her. But we also talk extensively every single day.

Our relationship, has, admittedly, moved at a frankly glacial pace compared to everyone else; I’m not complaining, just saying how it is. We didn’t have our first kiss until… I don’t know, our ninth date? Anyway, literally every single thing, every step that we take, is a first for both of us. I had never gotten a second date with anyone before her, much less kissed a girl. I really like her, maybe even am starting to love her, but I’m feeling dissatisfied with our level of intimacy, and also feeling ashamed for feeling dissatisfied. We’ve had a grand total of six kisses, and I’m always really conscious of her feelings and ask first, and always accept no as an answer, even if it smarts. Though not nearly as much as it does when she seems to hesitate before answering, which is really confusing as well as painful. It makes me worry she’s only agreeing because she thinks it will keep me happy. I feel dirty, greedy, selfish, because I really want to spend more time kissing her, even though I really love our conversations. But if something doesn’t change… I don’t know. I feel unwanted, undesirable, and… yeah.

The worst part is, when I try to voice the subject, I literally croak (seriously, it feels like my whole throat closes up), and I can’t get out a single word. Because I’m terrified that this amazing girl will think I’m only after one thing and she, the happiest thing in my life, will leave. And numbers or no numbers, I don’t like my odds of meeting someone else before I’m in my 30s.

I have zero expectations of her, but my desires keep getting louder in my head. And I’m trying very hard not to be disgruntled that just last week, she asked me down for the weekend to help housesit for her parents, and that in two whole days, we didn’t kiss until I was getting in the car to leave. That bugs me WAY more than sleeping in completely separate rooms. I’m not trying to suggest, ask, much less push for too high a degree of intimacy. And of course, I still feel guilty that this bugs me in the first place. The only comfort is that she admits that she “really, really, really” likes me, and that she’s sorry “if it doesn’t always seem like that” because she “sucks at showing emotion and super f

king awkward at expressing affection”.

I guess what I’m asking is, how do I keep from clamming up long enough to talk about these things?

So, yeah, this is all one tangled up mess of emotions on my part, that I have zero baseline for. I’m in the Pacific without a paddle, and any advice you have to offer on any of this would be great, because I’m clueless.

Thanks, 

Molasses In January

DEAR MOLASSES IN JANUARY: Let’s roll this one from the top, MIJ: there is absolutely, positively nothing wrong with wanting physical intimacy. That desire is 100% valid and legitimate. You’re not being greedy or perverted or selfish or disgusting because you want to make out with someone you’re attracted to. You’re a human with a sex drive and you want your romantic relationship to have a sexual component as well. And honestly, sexual satisfaction is an important part of any romantic relationship.

If one partner’s needs aren’t being met – or if their needs are being overridden by their partner’s, for that matter – then that relationship is going to fall apart pretty damn quickly.

So the fact that you’re frustrated and wanting more is completely understandable and completely legit.

But unless your girlfriend is secretly Jean Grey or Betsy Braddock, she has literally no way of knowing that you feel this way. And since you aren’t David Haller or Charles Xavier, you don’t really know how she’s feeling either. For all you know, you’re both sitting there wishing that the other would freaking say something about the physical side of your relationship.

Since neither of you are telepaths, the only way this is going to change is if one of you actually opens your mouth and make the words fall out. And since somebody’s gotta be the first person to start the conversation, it may as well be you.

Now I get it: trying to express a need, especially when you’re worried that you don’t have the right to feel this way, can be intimidating. You’re understandably worried that if you draw attention to the problem, then your entire relationship is going to explode. But by the same token, nothing is going to change, either.

Here’s what you need to do MIJ. You need to have The Awkward Conversation, in all it’s glory. This means that you need to go into it knowing that this is going to be awkward, acknowledging the awkward and pushing through the awkward. Here’s how it works:

First, you need to schedule the talk with your girlfriend. This is important because you need to block out time to actually hash this out when you won’t be interrupted or have to rush things. Start with saying “hey, I really want to talk about our relationship and where it’s going. Nothing’s wrong, I just want to check in with you about things. Can we get together on $DATE at $TIME and talk?”

Next, you want to lay things out in order:

1) Acknowledge that this is going to be a little awkward for you because you’re nervous to bring this up and you may need a little time to get through it.

2) Tell her why you’re nervous – you are feeling awkward about bringing this up because you’re worried that she’s going to judge you, be upset, think that you only want sex… whatever the exact fear is that’s keeping you from just saying whatever it is you need to say.

3) Explain how you feel; in this case, that you love this relationship with her but you feel like there’s a physical component that’s missing. You want to be respectful of her boundaries and limits, but you also want more than you’re currently doing. Make sure that you explain it in terms of why this is important to you and how you’re feeling. Be sure to frame it as how you feel, not how she makes you feel. This is your issue, not hers.

4) Explain what you’d like to be different – in this case, being more physically intimate.

5) Explain how you feel this would improve things.

6) Say “… and how about you?”

Now step back and listen to what she has to say. Give her the same space and courtesy that she’s just given you and let her share her side of things. This will likely be as awkward for her as it was for you, so be patient and let her wrestle through it without judgement.

Once you both have your cards on the table, now you’re able to find a way to move forward. This may involve some compromise or patience, or it may be that she feels exactly the same way you do and didn’t know how to express it. You may work out a way to express your affection with one another more easily, you may find yourselves having to have a couple more conversations… or you may just end up leaping on each other.

But nothing can change until you communicate with one another. So sit down, grit your teeth and use your words. The Awkward Conversation may be uncomfortable, but if you can muscle your way through to the other side, your relationship will be stronger and better for it.

Good luck.

DEAR DR. NERDLOVE: I would first like to thank you for creating a blog which helps men navigate the dating world in such a non-toxic and positive way. Your advice regarding nutrition, dress, and internal validation has helped transform me from a 22 year old virgin into someone with a stable sex life.

However, lately I’ve been “falling off the wagon” in regards to my self esteem: my most recent causal encounter started off ok but on the way back home and during pillow talk she kept asking me about 20 questions regarding what I thought of her. These ranged from “Why would a white guy find a black woman attractive?” (which she said she was just seeing if I had a weird fetish) to “What made you think you had a chance?” (She was talking to a very drunk burly guy and thin scrawny me happened to peak her interest). She was legit grilling me so I flipped it on her asking “Hey wait, don’t you believe you deserve a guy like me?” and she flat it answered “not really.”

Under normal circumstances a guy would be infatuated by that, but to me, I thought to myself  “So wait, you would’ve just went home with anyone simply because they acknowledged you?! Not for personal fun, but status?!”

My only previous partner was a Russian girl whom I’ve spent a wonderful 3 months with before she decided to call it quits. She believed she was “asexual unless she’d had a beer” due to nervousness (which I believe given her previous statements about how she was feeling) and we’re still friends.

But sometimes, I get second thoughts like “Oh woohoo, I only bring home desperate women,” “Girl #1 was only having a confused identity crisis” or “Self esteem? More like self-delusion!” I find that these thoughts are an absolute anathema to everything I’ve worked to achieve lately, yet, they’re here and are giving me a hard time.

My wingwoman reassures me that this isn’t the case, and 90% of the time I stay positive, but I believe that the disgusting humans-can-be-ranked ideology that my most recent partner had expressed somehow managed to rub off on me and is making me second guess my self-worth, even after I went through so much to accomplish unconditional self-love.

With this in mind, how would a newbie cope with such a situation?

If it’s relevant, I was also diagnosed with Aspergers Syndrome, which makes it difficult to read certain social cues.

Patient Zero

DEAR PATIENT ZERO:  First of all, PZ, I want to say congratulations! You’ve made some serious progress and you should absolutely be proud of how far you’ve come. You’ve developed some skills and confidence and that’s awesome… which is why it’s a shame that you’re letting your own doubt bring you down.

Here’s what’s going on, PZ: she’s trying to reassure herself that you actually like her. Her low self-esteem has convinced her that she’s undesirable and that the only reason why a guy would go for her is because either he has a race fetish or because he thought she was beneath him and an easy score. Then this cool guy rolls in, apparently not even intimidated by the drunk burly dude talking to her and makes his interest known? She’s got that voice in the back of her head saying “It’s a trap!”

She’s not saying that she’d’ve gone home with anyone, she’s trying to figure out why a guy as together and awesome as you was into her. That’s not someone desperate, that’s someone who thinks you’re awesome and has a hard time believing you’d think she was awesome too.

Sometimes you just have to accept that hey, maybe you’ve got it going on, even if your own jerk-brain is telling you otherwise. Stop letting other people’s self-doubt throw you, PZ; it’s not that they’re desperate, it’s that they recognize your value but can’t find their own. That’s all.

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: Due to some mental and physical health reasons I moved from my home to San Francisco where I am currently attending college. I have had little to no success with dating outside of a relationship I was in through OkCupid that ended about a year ago. I also used to do approaches at my old school with some friends of mine and we had some minor successes.

I saw your video on when and when not to flirt and I found it both informative and troubling. When I did used to do approaches I would almost exclusively do it at school, but since you said that doing that is normally seen as rude or bothersome I have been hesitant to try it here. The thing is when I’m at school is the only time I am around women on a daily basis. I can only go to bars once every two weeks or so because of my poor college kid financial situation. This has been taking a toll on my mental state in terms of provoking feelings of depression and self-hatred when I see a girl I find particularly attractive. I feel powerless and alone.

TL;DR: I wanna approach girls, because it feels like it’s the only thing I am doing that might work, and everything else I’ve been doing doesn’t. It is making me unhealthily sad. Please help.

Go, No-Go

DEAR GO, NO GO: It’s not that there are very specific places where you can meet women and these are the ONLY times that you can approach them, it’s that you should understand the context that controls social expectations and respond accordingly. Certain bars, for example, are explicitly set up for people to meet and hook up. Because flirting with strangers is considered to be part of the point of being there, it’s acceptable to go to these locations and approach many women over the course of an evening.

On the other hand, trying to hit on someone on the bus, subway or other form of mass transit is a bad idea; most people are just trying to get through their commute without being bothered. 

This doesn’t mean that it can’t be done. People HAVE gotten dates from someone they’ve met on the subway or on the bus or on a plane. However, it requires extremely strong social calibration, a great deal of experience and a careful sensitivity to the other person’s interest and comfort level. This isn’t even for someone with varsity level social skills, it’s for someone with pro-level skills.

But there are also liminal spaces out there, spaces that aren’t explicitly for meeting and mating but are still social. Classes, for example, are one of those spaces. College is an explicitly social space; you don’t just go to your lectures and then go home, careful to never say a word or make eye-contact with your fellow undergrads. It’s expected that you’re going to talk to your classmates and fellow students. In fact, college is one of the last times when socializing and making new friends will be as simple and effortless. However, this requires a different approach than when you’re meeting people at a single’s bar. You don’t want to be the guy who glides through school like a horny shark. While you can flirt with many, many women over the course of an evening at a bar, doing the same on campus is going to be weird – especially if it’s a small school.

So by all means, feel free to strike up a conversation with someone attractive that you see on campus. This is an expected part of the college experience. Just don’t treat it like you’re at the club. You can’t be as aggressive — especially physically or sexually aggressive – as you could be at the bar, nor should you have the same energy level. Take it down a notch or two and start with a conversation and see how things go. If the two of you click off the bat, then by all means, see about a brief date, even an instant date to get coffee or something. If there’s some chemistry there but not quite enough for an immediate “hey, do you want to go get coffee?”, then let it build over a couple of days or weeks before you ask someone out on an explicit date. And it should be a date; not to “hang out”, not to “get together”, but an unmistakable date.

Just, for the love of God, don’t be like the would-be PUAs who line major thoroughfares like Eaton Center in Toronto that make the act of walking down the street akin to running a gauntlet of aggressive douchebags. The social contract at college doesn’t allow for that.

Good luck.

DEAR DR. NERDLOVE: I have this problem. After years of social anxiety, having been called creepy before (and not really knowing why), and reading so many things on the Internet about women complaining about men approaching them and being a nuisance, reading so much about signs that you shouldn’t approach (and next to nothing about signs you should approach), I always just assume now that whenever I see a woman, she doesn’t want me to talk to her or anything, unless I see proof she does want to (and my definition of proof is very, very strict). Even if I’m at a setting where talking to other people is normal. Even if I’m actually acquainted with her or we’re in a group together, and in the latter case, I pretty much only talk if I need to, or if she says something to me first.

So my question is, how do I break out of this mindset?

Not So Strong, Silent Type

DEAR NOT SO STRONG, SILENT TYPE:  the first thing you need to recognize is that women venting about rude, excessively aggressive men isn’t the same thing as them condemning the entire gender. The problem isn’t men, it’s men who don’t understand things like the social context or that a woman who’s got her Murder Face on and is walking like she’s searching for the Holy Grail doesn’t want to be hit on by strangers. If you’re able to recognize “thanks, but no thanks” as the refusal that it is instead of a sign to try harder, then you’re ahead of the curve. The problem here is not recognizing the context of who was saying what, the context of it all and recognizing that some opinions are explicitly more radical than normal society would call for.

The next thing you need to realize is that, as I just said to Go, No-Go, there are places where approaching strangers is accepted as par for the course, places where basic socialization is acceptable and times when it’s just a plain bad idea. Now this doesn’t mean that any social contact is a horrible idea outside of these areas; it just means that you adjust your approach to your circumstances. The social contract varies depending on things like the venue and the time of day. Behavior that’s acceptable at a rowdy bar at 11:30 at night is going to be incongruous at best, disruptive at worst at 11:30 AM at Whole Foods. Similarly, behavior that’s fairly common during the day on a busy street could be seen as being threatening at night when there’re far fewer people around.

Learning to recognize and adapt to the context and circumstances is a big part of developing your social calibration. And to be honest: it’s not that hard. If you can understand that you should be quiet at the library and the movie theater, then you’ve got a fairly solid grasp of how social calibration works.

The next thing is to understand that there are differences in both approaches but also acceptable and unacceptable behavior. Striking up a conversation with someone you don’t know isn’t automatically like cat-calling a stranger in the street, and next to no reasonable people are going to equate the two. The guys who’re following women yelling “yo, you should smile more” and the guys who’re planting themselves in front of women to force them to stop and talk to them are very different from the guy who starts to talk to the person in line in front of them at Starbucks. While there’re certainly folks who feel that talking to them before their coffee is a capital offense, that’s hardly the same as the guys chasing women down Ocean Drive in Miami, trying to get their number.

It’s the difference between the guy who says “hello” to someone on the street and the guy with the clipboard who refuses to take silence and being ignored as an answer.

And then there’s the fact that women will let you know if they’re interested in talking to you. And, contrary to popular belief, these signs really aren’t that subtle. The most common example is what’s known as the “plausibly deniable conversation starter”. If you’ve ever said something loud enough for others to overhear and respond to, then you know exactly what this is: somebody making an observation or statement that’s intended specifically to prompt a conversation. An observational opener – something like “man, this line’s taking forever”- is a classic example of a conversation starter that she can pretend was just muttering out loud if nobody bites.

But even if you’re afraid of starting a conversation in places where conversation and socializing is explicitly permitted, then you may want to consider going to events or meet-ups where conversation isn’t just encouraged, but almost required. Team-based activities – from skee-ball leagues to amateur sports teams to pub quizzes – make socialization necessary. You have to work together as a team, and unless one of you is secretly an omega-level telepath, this requires actually talking to each other. Other events like board game nights at your local game shop or singles mixers are other great places to go where you’re expected to talk and share and mix and mingle with people you haven’t met yet.

And honestly? If you feel that you can’t talk to people you already know, or in explicitly social settings or that talking to people in those settings is going to make people feel weird? Then one of the best things you can do is talk to a counselor. That’s a pretty good indicator that you’ve got some emotional scarring that you need to unpack and work through. It sucks that you got called a creeper, my dude, but if you’re letting one incident through you for that much of a loop – especially if this was in, say, high-school – then you need to learn how to let go of the past and move forward.

At the end of the day, your wanting to be social isn’t a burden on other people. It’s part of how the world works. All you need to do is work within the social context of the situation and just be aware of the other person’s interest and comfort. And believe me: it’s not that hard… especially if you spend some time working on your social calibration.

There’re women out there who would love to talk with you, my dude. You just have to trust yourself enough to open up to them.

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:  About eight years ago, I was diagnosed with a brain tumor. It’s recurred about four times since. Doctors throw out the words “inevitable” and “incurable” when talking about my tumor, especially when talking about its recurrence. As a result, I effectively have an expiration date. Not necessarily a scheduled death date, but a date before which I’m best used. Metaphorically.

Anyway, my expiration date is about ten years out. But ten years is a hell of a long time to be alone. So I guess my question is… At what point in the dating process is it considered acceptable (or expected) to reveal that you have an expiration date?

Best Before 2028

DEAR BEST BEFORE 2028: Holy crap.

I don’t really know where to start, BB. I want to say I’m incredibly sorry that this has happened to you, but I realize that this is ultimately kind of hollow. I’m in awe of your attitude, that you’re making a point to live while you’re still alive; many people when finding out they have an expiration date – even if it’s years down the line – tend to give up. It says a lot about you and your strength. I have no idea what I’d do in that sort of situation.

(And honestly, having had to deal with my father’s and grandmother’s estates, the old joke of “max out my credit cards” isn’t really funny anymore.)

You’re right: ten years is a long time to be alone. And the fact of the matter is: none of us really knows when we’re going to die. Even having a certified expiration date – as in your case – doesn’t necessarily mean that we’re going to make it that far. You might get hit by a meteorite tomorrow morning. You might end up beating the odds and holding on for decades to come. So there’s always an element of risk when it comes to dating someone.

But those are – to quote Donald Rumsfeld – the unknown unknowns. You’re dealing with something known, and something that could very well directly affect both your quality of life and the life of a potential partner… and that’s the sort of information that someone considering sharing their life with you has a right to know about. Unfortunately, I don’t really have any easy answers for you. Rolling it out early on is going to scare a lot of people away. On a purely practical level though, there are going to be many false starts – flirtations that go nowhere, first or even second dates that just fizzle out because there’s no spark to be had. Having to explain each time about your health issues is going to be emotionally draining and possibly even scare off people who might otherwise be a match because… well, Hell, that’s a seriously heavy load to drop on someone.

It was hard as hell when my father told me he had inoperable cancer. I can’t even imagine if someone I just MET told me that.

Speaking strictly for myself, I’d recommend holding it back until the other person has gotten a chance to know you, to invest a bit more in you, so that they’ve started to think more about at least the medium-term possibilities of a relationship if not the long-term. At that point, their level of emotional investment, having gotten to know you as you rather than Man With Expiration Date, is more likely to make them at least consider how they feel without automatically hitting the eject button. But at the same time… I can see how people might see that as cruel and manipulative and might feel as though they’ve been led on by this. And there’s still no guarantee that even someone who was starting to think about where this relationship was going is going to be willing to stick around when you explain to them about your circumstance.

Even a strictly casual relationship is going to be tricky because unless you’re both unfeeling automatons, there’s going to be some mutual affection and caring going on. Knowing that somebody you cared enough to share your body with, if not the full extent of your heart, hid a secret like this from you can be incredibly painful. I could see an exception being made for a one-night stand, where you weren’t going to see each other again… but then again, plenty of relationships have started from one-night stands so…

Calling it a complicated situation is putting it mildly.

Because unfortunately, the specter of The Big C is going to scare a lot of people away. In a lot of ways, it means knowingly choosing to take part in the first act of a tragedy. Many people aren’t going to be up for that. They may not be strong enough. They may be too afraid of the inevitable pain of loss, or the complications that would arise. Someone who’s looking for a life-partner now may not have thought about the fact that being with someone (presumably) for life means being there at the end of life. It’s easy to not think about it when it’s presumably 70 or 80 years away. It’s another entirely when it’s within two years. Or five years. Or ten years. That can make it all too real for a lot of people. And they’re going to self-select out of the dating pool with you because they’re not going to be sure they can handle that or they want to deal with that so (relatively) soon.

I will say – in as much as there’s a bright side –  there’s a bit of cultural confluence right now. A lot of YA fiction has tackled the question of dating someone with a chronic or even fatal illness. John Greene’s young-adult novel The Fault In Our Stars – about a pair of cancer patients who fall in love – hit peak popularity, complete with a movie adaptation not that long ago. One of the themes of the book is that love – even when it’s all too brief – is transcendent and makes even the pain of losing someone worth it when it comes with the experience of loving them.

I’m not saying it’s going to make tragic love stories the new must-have fashion in relationships, but I do think it’s going to prompt at least some discussion over what it means to love someone even when you know that it can’t possibly last as long as you’d like. And that, I think, is what you – and your future partners – should focus on; the transcendence of love and intimacy.

I wish I had an easy or uncomplicated answer for you, BB, but I don’t. The best I have are a lot of very complicated, very tricky options without anything resembling certainty or assurance. A lot of people are going to be unprepared to date someone in your circumstances. Even people who think they might be ready may well find that they aren’t able to handle it, no matter how much they may wish to.

All I can say is that the people who can, who want to try and who will fight tooth and nail to make it work… they’re rare. They’re hard to find. But they are out there. And when you find them, they are more precious than diamonds and gold. They are the ones who understand that loving someone, even knowing that you’re going to be saying goodbye to them some day much sooner than you’d like, is never wrong. And the power and intensity of that love, the time spent together and the memories that remain are always worth it.

Good luck.

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