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)

DEAR DR. NERDLOVE: I recently went through an extensive security clearance update, and during that process (which, for my level of clearance is quite extensive) my brother-in-law and sister-in-law were investigated for various things.

During that investigation it was revealed that my brother-in-law had been having multiple affairs during the marriage and was currently carrying on another long term affair. I didn’t inform my sister-in-law immediately with the information, because at the time I didn’t think any good would come from it.

This week, this affair started to affect my husbands business in the form of a new secretary; she proceeded to tell everyone in the office all about her liaison with my brother-in-law, including customers. So my husband and I told my sister-in-law about the secretary… and all of the others.

Of course she has now accused us of lying and trying to profit from telling her. Not sure what we would be gaining…

Anyway, now my husband has disowned her, and I was thinking of just posting everything online and letting the chips fall where they may.

So my question is do I have someone secretly give her the photos, emails, texts, voicemail recordings etc. or do I just cut ties and let her figure it out on her own? You were definitely right when you said in a previous article that the wounded always “shoots the messenger”,even when it’s family. Any insight on how to repair this and move forward? Or is my husband right, and we should just cut ties and forget them and when my brother-in-law eventually leaves for the young girl tell her I told you so?

Caught In The Middle

DEAR CAUGHT IN THE MIDDLE: My advice is to stay the hell out of it, CitM. This is humiliating enough for your sister-in-law.  It’s bad enough that her husband is cheating on her; having other people rubbing her nose in it just pours salt on an already gaping wound.

Your brother-in-law is already twenty pounds of jackass in a five pound sack and his current paramour isn’t much better. It’d be far better for your husband to apply the Chair Leg of Truth upside his brother’s head; not only is he treating his wife abominably, but it’s also spilling out into your lives as well.

But your sister-in-law, unpleasant as she may be acting right now, is the victim here. I’m not surprised that she lashed out the way that she did; she’s feeling hurt and humiliated. She’s having an entirely unsurprising reaction to humiliating news; accusing you of making it all up is a defense mechanism. It’s a way of trying to force this to not be happening. She’s being incredibly unpleasant, yes, but she needs sympathy right now.

Now, if you want to give her some leverage in the divorce proceedings that she really should be initiating… well, offering her the evidence will certainly give her a leg up on the guy who’s not only cheating on her but dragging everyone else into his mess. But otherwise: keep out of it. This isn’t your fight, and the petty satisfaction isn’t going to be worth the profound pain that you’ll inflict on her if you decide to say “I told you so.”

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 writing to you because I think I have a problem with my girlfriend and I’m not sure how to solve it. First of all, English is not my first language so I’m sorry for any mistake in my letter.

I’ve been with her for 6 years and we moved together last year. It’s been great so far and we’re still very happy together, or at least I think we are. I’m not into the idea of marriage and family but, if I was, I’m sure she’d be the girl I’d want to spend the rest of my life with.

I think it’s perfectly normal for a couple that has been together so long to fall into a sort of “routine” and not be as passionately in love as one is in the first years of the relationship. We still have a good time together and have a regular sex life, we’re still very attracted to each other and the moving together part has been mostly good.

So my problem started a few weeks ago, when she first expressed the interest in seeing other people and having an open relationship. We discussed it a few times and she’s always the one to be more open and interested in the idea. I asked her if this was about someone else in particular and she said no, just that it was something she thought could be good for us and could “break the routine”, allowing us to have new experiences knowing that we will be stronger because of this. 

She told me that she’s so sure about our relationship that she’s willing to do this because she knows she wants to be with me, it’s just about new experiences and not about me or any doubts about or relationship.

That’s all fine and it completely makes sense to me. I would potentially be interested in meeting other people and having an open relationship, but the truth is that it scares me. Rationally speaking, I know monogamy is against our nature as animals and it’s very hard to be with the same person for many years without feeling the need of exploring new things.  On the other hand, I never considered open relationships to be a good idea, and there’s where I’d really love your opinion. I don’t know anybody who’s ever been in one, but I’m afraid it might lead to heartbreak, jealousy, trust issues and breakup.

My girlfriend and I agree on the need to establish some ground rules, like no exes or no close friends. One of the rules she suggested was “no sex, just making out or fooling around”. Do you think it would be better – or less hard to tolerate? Do you have specific advice about establishing rules?

I know it’d be hard for me, but I also want to say yes to my girlfriend and try to make it work, if that’s what she wants. She brought it up four or five times already, so I’m sure it’s something she’s really thinking about. The thought of her “wanting more” scares me and upsets me, but I don’t know if it’s just pride or the realistic chance of losing her. I want to be mature about this and enjoy all the positive aspects, but I just don’t know if something like this could ever end up well for the both of us.

Thank you for you time

Opening The Door

DEAR OPENING THE DOOR: One of the biggest – and most damaging – lies that we tell ourselves about relationships is that monogamy is natural and easy. We get told that if we really love someone, then we never think of anyone else and we never want anyone else. This cultural lie has caused more unnecessary emotional pain and trauma in relationships than… damn near any other myth we tell about relationships, really. The truth is that, we’re novelty-seeking mammals and part of the whole package is that we are literally built for multiple partners. Biological issue like the Coolidge Effect kick in and suddenly sex with the same partner doesn’t have the same zing as it did before; our brains don’t produce the same levels of dopamine and oxytocin during sex as it does with a new partner.

Now the fact that monogamy isn’t our default state doesn’t mean that it’s bad, or wrong… just that it’s difficult. It’s perfectly normal to want to sleep with other people, no matter how much you love and desire your partner. A monogamous commitment just means that you choose not to.

But monogamy isn’t for everyone and that 7-year itch isn’t entirely BS. For a lot of people, there comes a point where they may love their partner… but they also want to sleep with other people.

And that’s where your girlfriend seems to be, OTD. She’s made it pretty clear that she really wants to open things up. So clear that, honestly, I’m wondering if the next time the topic comes up, it’ll be as an ultimatum, instead of a request. You, on the other hand, are pretty sanguine about it. In theory, yes, it’s an opportunity for you too. In practice, it may not be. In general, it can be easier for women in open relationships to find partners than it is for men. Women tend to be a little more cautious around men who claim to be open or poly, for good reason; many a woman has found out after the fact that the other partner in the “open” relationship had no idea about the arrangement. Men… tend to not care quite as much.

But that aside… what are the risks to your relationship? Will opening things up lead to jealousy or heartbreak? Could it lead to the end of your relationship? Sure, that’s a possibility… but then again, that’s a possibility in a closed relationship, too. Monogamy isn’t a Protection Against Break Ups spell; closed relationships fall apart just as readily and often as open ones.

By that same token, however, the same things that help preserve a closed relationship are the same things that preserve an open one: communication, intimacy, communication, gratitude, sex, and communication.

Does this mean that opening things up is a good idea for you? That’s harder to say. Just as monogamy isn’t for everyone, neither are open relationships. It takes a high level of trust and open communication to make an open relationship work; because it involves other people and the thrill of the new, it’s easy to inadvertently let your main relationship suffer while you’re caught up in that New Relationship Energy.

It’s pretty clear that you’re not really keen on the idea. But at the same time, there have been plenty of couples who started off with one partner begrudgingly agreeing to things and then starting to love it themselves. Maybe that’s you. Maybe it’s not. Only you can say.

What I will say is that you two need to do a lot of research and talking before you agree to anything. Trying to open things up when you’re unprepared is a great way to do a lot of unintentional damage to your relationship. So you and your girlfriend need to do your due diligence and a hell of a lot of studying. I strongly recommend that you start with several books: Opening Up by Tristan Taormino, More Than Two by Franklin Veaux and Eve Rickart, and Mating In Captivity by Esther Perel. The first two will help give you practical advice on the best practices with regards to opening up a relationship; the third will help you understand why monogamy can be such a challenge. I also recommend Building Open Relationships by my friend Dr. Liz Powell, which is available for pre-order.

If – and this is a mighty big if – you do decide to give an open relationship a chance, then start slow. Even if you think you’re ready for things, diving in head first is often a recipe for disaster. It can be incredibly demoralizing when your girlfriend goes out and immediately finds a partner, especially when you’re still getting used to the idea.  Even just “fooling around”, might be enough to kick your soul in the nuts. Take baby steps at first: kissing and make-outs to start, and see how you feel. You may realize that you’re cool with it. Or it may be a kick in the gut at first, but with time and communication, you’ll find that you’re ok.

And it may be that you will have to ask your girlfriend to hold up while you look for a partner. If your relationship ends up functionally only open on her side, this can torpedo something that might work if things were more equitable. The fact that you are looking for a little strange doesn’t negate your responsibility to each others’ happiness and well-being.

Jealousy will happen. But if the two of you can communicate clearly, openly and with empathy and compassion, you can work through it.

This can be hard… but it could also be amazing. Only you will know if this is something that’s right for you. So do your research and do a lot of talking before you decide, one way or the other.

Good luck.