DEAR DR. NERDLOVE: This is my first time actually writing something like this, but I’ll do my best: 

I am a 20 years old woman, just turned 20 actually, and haven’t really dated any one or had sex or even kissed or held hands, or hugged a significant other. I don’t think it’s weird. My problem is, I know what I want in life and I’ve done a lot of research on how to talk to or meet potential SO, but never really executed them. 

When I watch shows, I even write down tips on how to flirt with people, but that never goes anywhere either. I don’t have much confidence in myself (possibly because I also call myself a raccoon, but that’s besides the point) I have less confidence when it comes to my approaching someone, but I fear if I don’t, no one would approach. 

I know I’m not cute, maybe a little on the unattractive side, I know that, but I try everything else to make up for that fact. 

Look, honestly, I don’t feel my situation is unique and I don’t think it is, but I desperately need some advice on what I should do to get more confidence in talking? 

Wallflower

DEAR WALLFLOWER: Here’s the thing about social skills, Wallflower: they’re skills. They’re not innate; they’re something that you can improve with deliberate practice. But you have to actually practice them. I know a lot of folks who can tell you all about how much studying they do, how much research they’ve accomplished, how many books they’ve read or even courses and seminars they’ve attended… but they’re still stuck. And the reason for that is because all the studying and theory in the world isn’t a substitute for actual boots-on-the-ground experience. You can take all the notes you want on how folks flirt on TV or in movies — God knows I reference plenty of them as examples — but none of that matters if you don’t put them to work.

That’s why you can’t study or theorize your way to confidence. Confidence is built through experience. Confidence isn’t about succeeding or knowing you can’t fail, it’s knowing that doing something won’t destroy you. Fear + survival = confidence, and that only comes from real-world application.

Now that being said, this doesn’t mean that you need to go out and start hitting on folks for practice. The great thing about social skills is that you can practice them in low-stakes, low-investment environments. At 20, you’re in a good position to actually practice being social. If you’re going to college or university, there’re an almost infinite number of opportunities for you to go to events or gatherings and just work on talking to people. Not to hit on them or flirt or find a partner, but to just talk, without an agenda. If you go with the mindset that you’re just practicing, that you’re only out to meet people and enjoy yourself, then it’s much easier. By not being attached to a particular outcome, you’re better able to relax and just be in the moment, instead of weighing every word that comes out of your mouth or the nuance of every gesture or intonation from other folks. All you’re doing is talking.

The more practice you get in just talking with people and joking with people, especially when it doesn’t “count”,  the better you’ll do when you’re in a place where you do want to flirt and joke and maybe see if someone wants to grab a coffee somewhere. The same skills you apply to joke and make friends are the same skills that ultimately help you find a significant other.

Even if you’re not going to college, you have opportunities to practice your social skills. A public-facing job — whether its in sales, customer service, even service industry jobs — means that you’ll have to talk to many, many people from all walks of life. It’s very hard to not become more socially fluent and at ease in those cases. You’re literally required to talk to people and put in the proverbial 10,000 hours of practice.

However, one thing you should definitely stop doing, even if you do nothing else, is talking yourself down. I get the impulse to insult yourself or make fun of yourself before anyone else can; God knows I’ve done it enough in my time. However, constantly insulting yourself, saying that you’re unattractive or that you’re a raccoon or what-have-you affects your self-image. Even if you’re only doing it jokingly, when you say and think things often enough, you train your brain to accept them as true. Self-deprecating humor quickly goes from being jokey-jokes to how you actually feel about yourself and how you expect others to treat you. Learning to love yourself, even hype yourself up is important, and it goes a long, long way towards helping you build up your confidence and self-esteem.

Good luck.

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

DOCTOR’S NOTE: Occasionally I get a letter that is less of an entry for Ask Dr. NerdLove and more of an a prompt for a longer form response — something between a Post-Mortem and one of my “how to” columns. This is one of those times, which is why today’s entry will be both longer and formatted a little differently than my usual columns.

DEAR DR. NERDLOVE: Well , where can I start? The simple thing is that I don’t feel good enough to talk to women. Currently I’m training like hell to be more attractive (I go to the gym x6 times a week, in my country we are not in a lockdown) but it takes time to get the type of body women are attracted to, at least on Tinder. First of all, I’m not looking for something serious and I know for fact that for casual relationships (or casual sex for that matter) women like muscular/fit men so… well I must train everyday but Doc, I feel tired you know? I mean, don’t get me wrong, I enjoy training but it’s exhausting! I even take SARMS to accelerate the process!

I read your articles, but I disagree with what you said about casual sex and women. For example, women are the gatekeepers of sex because they are the ones who are approached , that give them by default the power. Why you believe that for example, on tinder men don’t get many matches? I mean, I know some men do get tons of matches but.. see those men, what they have in common? Good looks and muscular body, and yes, I know that Tinder is not real life but women in general will prefer muscular men for casual sex. So, Doc how can I be less tired? I feel that for casual sex I must be muscular to have a chance…

Gym Rat

DEAR GYM RAT: Welp, there’s a lot to unpack here… but I think we all might benefit from throwing the entire suitcase away instead.

This is going to end up being a long one because there’s a lot to cover. And while this is going to sound like I picked your question just to bag on you, I honestly didn’t. I want you to find the kind of sex you’re looking for, my dude. But to do that, we need to dig in pretty deep because I think you’re coming at all of this from the wrong angle.

Let’s roll this from the top, GR, because you’ve got a lot of fundamental errors going on here at… well, almost every level. I mean, even if I accepted your base premise (and I don’t) that women are the gatekeepers and require muscular men for casual sex, you’re still doing it wrong. Training six days a week is how you end up severely overtraining and not only ruining your gains but running the risk of serious injury. Doubly so considering you’re using performance enhancing drugs of dubious efficacy and safety and a high likelihood of not even containing the ingredients promised on the packaging. I’m not surprised you’re exhausted on that level alone; signs of overtraining include fatigue, irritability and agitation and a decline in athletic performance.

Pain isn’t weakness leaving the body, pain is your body’s way of telling you that you’ve f--ked up your gains because you were so exhausted from over-training that your s--tty form led to tearing a muscle.

But as I said: that’s just if I either focus solely on your attempts to get swole or accept your base premise about casual sex and what women look for in potential sex partners. But I don’t and frankly, it’s flawed from the jump. And the hard truth is that it doesn’t matter how much you want to will s--t into existence, if the foundation of your beliefs are wrong, it doesn’t matter how much work you put in… you’re still not going to succeed.

Now, I picked your letter for a number of reasons, not the least of which being that a lot of guys have convinced themselves that they need to be jacked manly men in order to be attractive to women. This is something that comes up a lot, and it’s a belief that has almost become religious dogma among some men. In fact, dudes believe this so fervently that they’ll argue with women who tell them “dude, I like skinny guys/ dad bods/ chubby guys/ stocky guys,” insisting that these women are lying or would change their minds if they could get someone else. It doesn’t matter that these women are explaining their lived experiences and choices they’ve actually made; this goes against the dudes’ belief system and thus it can’t possibly be that their beliefs are wrong.

It’s especially amusing (for annoying values of “amusing”) when their citations are “dude, trust me,” “it’s patently obvious,” and “everyone knows this.” Other examples of “evidence” include imagining what other men are experiencing on Tinder without actual numbers and evidence, badly and deceptively edited “social experiments” on YouTube and elsewhere, and the existence of sexy dudes on TV or TikTok or Instagram.

You barely have to scratch the surface before you realize that most of the people who believe this are talking to other men about what women want as opposed to, y’know. Asking women about it. And the few times they try to point to women as proof, it’s almost always an individual saying something or a self-selected (and non-statistically significant) pool of people talking about theoreticals, rather than what they’ve actually done.

I mean, yes, if I were to be offered a choice of a guaranteed date and/or hook-up between Kat Dennings and a complete stranger, I’m probably going to choose Kat Dennings. But then again, my choice between being given a million dollars tax-free or a decently-paying 40-hours-a-week job doesn’t mean that men are inherently lazy and want to have riches handed to them. It means that, in the event that someone wants to give me stupid amounts of money with no strings, I’m taking the damn money. Because hey, as long as we’re living in fantasy land, I’m gonna roll with the fantasy.

But pointing out hot dudes on social media getting comments from thirsty women doesn’t really prove anything other than “people find conventionally sexy people attractive, film at 11”. It’s no more indicative of a universal preference than men commenting on sexy women’s pictures; it’s patently obvious that while dudes will go all wolf-whistle-jaw-drop-lip-bite over hot women, those aren’t the only women they’ll sleep with or date.

This is what happens when men only listen to other men about what women want. You end up with funhouse mirror versions of reality, based less on reality and more on a couple folks who’re pissed that someone else is getting what they want (and the grifters who prey on those insecurities). This is how you find dudes who’ll dissect everything about a celebrity and insist that by their calculations, he’s scientifically ugly because he doesn’t measure up to the new version of phrenology they invented.

Meanwhile as folks are going on about how only Magic Mike types get casual sex, women are screaming about Loki (not just Tom Hiddleston… Loki, specifically) or how David Bowie was the key to their sexual awakening in Labyrinth or how much they dig Sung Kang.

Similarly, the idea that women are the ‘gatekeepers of sex’ is wrong as well. This is a faulty premise that’s hung around for generations. The basic premise is that women “control who gets to have sex” because they “have the power to choose” which… yes? Women do, in fact, get to choose whether or not they want to have sex with someone. But so do men. In fact, men do the choosing first. Unless you are literally — not “emphatically”, not “exaggeratedly”, literally-literally — approaching every single woman you see for casual sex, you have been choosing people as well. You chose to approach this person, swipe right on that one, or otherwise attempt to get them to want to have sex with you before they ever had a chance to consider the question. Women have to have the right body type, the right presentation (make-up, hair, style), skin color, photos, etc. before men will ever talk to them. Clearly, men have all the power when it comes to sex and dating.

Seriously dude, it’s like you forgot the whole point of Tinder: it’s a double opt-in system. Both parties have to be interested in one another in order to make the f—ky-times happen.

The truth of the matter is that the idea that “women get to choose because men do all the approaching” has nothing to do with power and everything to do with the f--ked up relationship we have with gender roles and sexual dynamics. Men do the majority of approaching because we live in cultures that have punished women for being sexual for literally hundreds of years. Even now, when women are overtly sexual, express sexual desire or sexual autonomy, people lose their goddamned minds. You can see this in how people responded to Cardi B’s W.A.P, Megan Thee Stallion’s Thot S--t or, s--t, Madonna’s entire goddamn career. Women who are overtly sexy are demeaned, seen as less intelligent, less “valuable” and dudes yell at them for “attention seeking” — see, also, every female streamer on Twitch with so much as a hint of cleavage. Porn stars get beaten within an inch of their lives by their partners and it’s seen as being justified because “she’s a slut”.

Women — as has been pointed out many a time before — have the same insecurities as men do. They’re just as worried about being rejected as men are. They don’t want to approach someone or try to flirt with them only to get shot down. They have the same worries that men do when it comes to the sting of rejection. And then, on top of this, they have to factor issues like “physical safety” and the way a lot of men respond to being approached. A lot of guys will either assume that this is a trick or a trap and freak out… or assume levels of interest far out of proportion to how she actually feels and treat “hi, how are you” as “take me in a manly fashion right now.”

Small wonder that a lot of women won’t make the first move; it’s not worth the risk.

And even when they do, a lot of guys miss it; women making the first move doesn’t look like the oversexed singles on Too Hot To Handle, it looks like a woman saying “how’s your night going so far?”

But what about men getting fewer matches on Tinder? Well, funny thing about that: it’s because those same dynamics follow us online. In fact, those dynamics lead to men and women using Tinder in entirely different and contradictory ways. Men swipe right on as many women as possible in order to maximize the number of matches they get. They decide who they want to talk to after they match. Women, on the other hand, will swipe right selectively, and only on people they’re actually interested in. But what often happens is that they find that the guys they matched with in good faith were, in fact, not interested and unmatch them. And the guys who do message them will send a first message that’s less than 25 characters long. Not words. Characters. Including spaces and punctuation.

This disincentivizes women from swiping much at all. And while I’ve got a very, very large [citation needed] on your insistence that only certain guys get all the matches, it’s worth remembering that matches on dating apps are fundamentally meaningless. It only “counts” — as it were — if you actually, y’know. Actually meet up in person and go on a date.  How many matches you get doesn’t mean a damn thing; anyone can get matches. It’s about being able to make the connection, both in messages and in the flesh. Otherwise, all you’re doing is measuring your e-peen with a number that’s ultimately inconsequential and only has value to other folks who want to compare e-peens.

Which, in fact, leads me to my next point:

What are you actually looking for?

There’re a lot of ways to find casual sex — some more complicated than others. But a lot of times when men talk about looking for casual sex, they aren’t necessarily talking about a friends-with-benefits relationship or an ongoing connection without the expectations of commitment or monogamy but one-night stands and same-night hook-ups. More often than not, the guys who are hyper focused on “needing to be swole” or who matches with whom on Tinder think of casual sex as “meet up to f--k” with very little in the way of conventional dating between “meet” and “mate”.

In fact, the fact that this hinges on Tinder instead of… er, Hinge, is kind of a tell in and of itself. Tinder, after all, started out trying to be Grindr for straights; all about facilitating quick and easy hook-ups. Even as its overall usage has changed, Tinder is still synonymous with the concept of the zipless f--k. I mean, GR, you’re not exactly talking about not being jacked enough for Bumble, are you?

But the thing is: you can find casual partners on Hinge and Bumble. There’re plenty of women on there who’re looking for a guy they get along with, who they find attractive and who isn’t interested in something committed or even long-term. But the reason why this gets less attention is very simple.

It’s not really about sex. It’s about validation.

One of the beliefs that contributes to toxic and restrictive ideas about masculinity is the idea that a man’s value is measured in part by how much sex he has. The more desired a man is, the more manly he is. And since women aren’t supposed to like or want sex and are supposed to hold out for commitment, a guy who gets a lot of one-night stands must be very manly indeed. After all, if he’s so hot that he can get women to f--k without meeting the “marketplace value” of sex… well, he’s at the top tier of men, the mythical “Chad”. This is supposed to be the goal after all: f--k as much as you can before some woman manages to tie you down or forces you to settle for less than you “deserve”.

The problem is… this ultimately is pretty goddamn hollow. Not because sex is somehow more meaningful or something when you’re in a committed relationship — more on that in a second — but because ultimately, it’s not about sex. It’s about wanting to prove something — whether to yourself, to your peers or even just to the imaginary crowds in your head. It’s about filling the hole in your self-esteem that tells you that you’re not “worthy”. But if you bang a lot of strange, surely that’ll prove you’re desirable! That you have meaning! This will show all of those others — real and imagined — where you stand on the ladder of masculinity!

And it won’t. Because f--king people doesn’t heal your self-esteem. Hell, women will sleep with folks for a multitude of reasons that have nothing to do with the person they’re f--king and everything to do with themselves. Sure, getting off with a stranger you just met may make you feel like Studly Goodnight… but how do you square that sense of being “worthy” when they chose you because they wanted to send a message to their ex and you were the least objectionable option that night?

This is also part of why there’s usually more emphasis on picking up women or hooking up with different women on apps than finding an FWB; there’s more “glory” or “prestige” to be had (theoretically) in numbers. Sure, the sex with an FWB or a casual regular partner tends to be better because of the foundation of trust and communication… but doesn’t quantity have a quality all of its own? Even if you’re still left with nagging doubts and your insecurities don’t magically go away?

And to be clear: I’m a fan of casual sex. I’m a fan of same-night hook-ups and even of one-night stands on occasion. But having been on both sides of this particular equation, I can tell you from personal experience that there’s a very real difference between the kind of experiences you have when you’re pursuing casual sex because that’s how you roll, and pursuing no-strings sex and picking up women because you’re trying to prove something.

Which is why, GR, I think it’s really important to examine just what your motivations are. The focus — hell, the apparently near-obsessive need — to be jacked and to get chicks off Tinder suggests to me that this is less about your just being someone who likes to f--k and more about wanting to prove that you’re wanted. And again, I have been there and done that and built an entire career out of it and I am here to tell you: that feeling will never go away, no matter how many women you bang. If this is ultimately about getting the approval and validation from others — even if those “others” are mostly in your head — then all you’re going to do is numb that feeling temporarily… before it comes roaring back, just as strong and harrowing as before.

All of this is a long-winded way of saying, my dude: the reasons why you’re exhausted is because you’re trying to live up to standards that are not only completely made up, but that are virtually impossible to live up to. The Rock looks like he does because it is literally his job to look like that. His life and career are built around being so in shape that he becomes a thirst trapezoid… and even then, it’s entirely dependent on the role. You can see the difference between his early days in the WWE, his role in Snitch and Fast 6. The same goes for Chris Hemsworth, Charlie Day, Kumail Nanjiani, Simu Liu, Chris Pratt… any super-hunk you care to name: their super-jacked bods are the product of their entire lives being based around eating and training at intervals so strictly regulated that it’s virtually impossible for anyone else to follow them.

And the thing is, the people who care the most about this aren’t women… it’s other men. While yes, women like looking at hunky men, that’s not their prerequisite for casual sex. Here’s the baseline of what women are looking for when it comes to casual sex:

a) He’s attractive to them

b) He’s safe — physically and emotionally

c) The sex would be good enough to risk pregnancy, sexually-transmitted infections, the potential of physical and emotional violence and the societal consequences of being a woman who likes to f--k.

I mean, why do you think it’s still called “the walk of shame”?

Before you start going on about how being muscular fits into A or C, it’s worth remembering that not only do women like a wide variety of bodies and types, but that looking like you were carved out of marble and abs doesn’t mean you’re actually good in bed. Speaking for myself: I’ve slept with women who were model-gorgeous but thought all they had to do to be good in bed was just “show up”. Women, likewise, have oodles of stories of men who were conventionally hot or hung like porn stars and how awful they were at sex. One of the reason why women don’t like casual sex isn’t because they don’t like sex, it’s because men tend to see casual sex as a reason to just get off and go. After all, why bring your a-game if you’re never gonna see her again? Not to mention, this often comes with bonus points of calling her a slut or a whore afterwards.

While conventional good looks certainly help — nobody is saying otherwise — it’s not the only factor, nor is it the most important. A dude who actually radiates good sex, whether through being a skilled dancer, a great flirt or simply knowing how to build a sensual connection is going to have far more success than someone who’s pleasant to look at but otherwise an empty vessel.

Now, if you dig working out and strength training for its own sake then, s--t dude, go for it. Hit that gym, drink your protein shakes and eat all the cod and chicken breasts you can choke down. But focusing on trying to measure up to imaginary standards that’re held up by other men instead of what women are actually looking for is just going to mean that you’re constantly be under the gun. You’ll literally never be able to measure up because you’re convinced that you need to be superhuman. And worse, any success you do have won’t be satisfying in the ways you hope.

You’d do better to focus on social skills and learning how to build connections with folks, how to meet people in person and communicate and — again — demonstrate through word and deed that you’re worth banging because sex with you would be good. That’s not gonna come because you’ve got them boulder shoulders, it’s going to come because you know how to touch someone and how to move your body. You’ll have more confidence and self-assurance because you’ll be more focused on developing yourself as a person, not trying to rack up enough numbers that you’ll be able to reach the top of the Masculinity Scoreboard (before someone else kicks you all the way back down the ladder)

You’ll be less tired this way because  you won’t be chasing down a goal that is literally unobtainable. You won’t be as hung up on impossible goals and unrealistic standards and putting all your energy trying to get the approval of strangers, approval that doesn’t even have anything to do with the people you’re hoping to sleep with.

Finding sex partners, even for same-night hook-ups is about connecting with people, getting to know them and building relationships. Even folks who are open to having sex that night by someone they’ve just met — whether on Tinder or at the bar — don’t like being treated like a foregone conclusion or a sex-ATM. They want to connect with that person, make sure they have a vibe and chemistry and a reason to sleep with them, specifically. That’s gonna be a lot harder to come by if you’re convinced that a  deltoid and a bicep, a hot groin and a tricep are all it’s gonna take to make someone want to take you by the hand.

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: A few years ago I was in a relationship with a woman. We originally met through Tinder, but we did actually develop feelings for each other. Unfortunately, the timing of the relationship did not work out. We lived far apart from each other and with our busy schedules (she was an undergraduate, I was a medical student at a different university) we only got to see each other 2 or 3 times a month on weekends. After 6 months or so, I broke off the relationship and it was a painful experience. I regret how things ended, I regret the way I acted at times, and I still sometimes wish things could have worked out differently.

Jump to today, I have grown a lot as a person. I’ve learned a lot about myself as a result of mental health counseling and gained experience in romantic relationships. Now, I have learned that this woman will be moving to attend a graduate program at my university. I am debating whether or not I should try to reach out to her. I am concerned that she still harbors negative emotions towards me, but I think it may be worth the risk of reaching out through social media and gauging her interest in reconnecting. What do you think I should do? Would it be disrespectful to show up again after all this time trying to make amends?

Thanks in advance,

20/20 Hindsight

DEAR 20/20 HINDSIGHT: I see that it’s “get your ex back” season…

Before we get to your question, TTH, I’m going to go off on a bit of a digression. This is going to sound completely unrelated, but stick with me for a second, I swear I’m going to tie it all back in.

Mass Effect has long been one of my favorite gaming experiences; the trilogy, with its epic storyline and compelling characters has resonated with me in a way most games don’t. Recently, I’ve been plowing my way through the Legendary Edition, playing the entire trilogy in one go. I’m about 1/3rd to 1/2 of the way through Mass Effect 3 at this point and… well, this time around, ME3 is hitting differently. Part of what’s struck me about the third game — where the dreaded Reapers have finally appeared and the entire Milky Way Galaxy is in very real danger of being exterminated — are the reactions of the non-player characters, the civilians you encounter in areas like The Citadel. One of the things that hits a little harder this time around are the folks who are desperately searching for some sense of stability and normalcy. Some are pretending the crisis doesn’t exist, some are clinging to shreds of their old life and many are trying to find solace in relationships. Everyone is looking for a sense of calm in the storm, a little bit of familiar order in the chaos.

Now, back in the real world, one of the things I’ve noticed recently is an uptick in folks who are dealing with complicated feelings about their exes. A lot of them are folks who are hoping to rekindle things, or at least reconnect with them. This isn’t entirely unsurprising, in my experience. The last year and change — with the presidential election and attendant drama, the Jan 6th insurrection and, y’know, the global pandemic — has been a time of chaos and upheaval. In times when it feels like everything is going off the rails, it’s human nature to want the familiar and known. Nostalgia is a powerful narcotic and it’s very easy to let the golden glow of the early days overwhelm your memories of the bad times. An ex, even in a relationship that ended badly or needed to end is a known quantity. They represent a different time when things felt a little less chaotic being more in control.

Just as importantly, as we’ve all faced the very real risk of disease and death and social upheaval, there’s an understandable impulse to look at your life and your regrets and want to try to make changes. Sometimes that means looking back and wanting a second chance when you feel like you’ve made a mistake. Other times, you want to try to at least make amends for things you feel like you did wrong.

Which brings us back to your question, TTH.

If you’re a regular reader of the column — or you check the archives — you know that whenever someone asks me about getting back with their ex, I have questions for them that they need to answer, first. In fact, I literally just covered a similar situation a few days ago.

In case you missed it from last week, here’re the questions again:

Question #1: Why did you break up in the first place?

Question #2: Has the reason why you broke up changed?

Question #3: Why Now?

Question #4: Do you miss THEM, or do you miss what they represent?

Question #5: Are they right for you, NOW?

In your case TTH, questions #3 and #4 are the most relevant. Why now, and what, exactly, are you hoping to get out of this?

These aren’t idle questions to ask. Part of why it’s important to really dig into yourself and your motivations is because you want to avoid unnecessary pain and heartbreak, on your side and on your ex’s. One thing I’ve seen all too often are people who don’t want to get back with their ex… not really. It’s less about trying to rekindle an old flame or repair a broken relationship and more about the need of the moment. In that moment they want their ex back, and it feels real and immediate… but that moment passes. Sometimes that desire flares up because they saw that their ex has moved on. Other times, it’s because they’re tired of being alone or frustrated with dating and want to go back to a time when they didn’t have to think about it. And still other times, it’s about their feelings — unfinished business, regrets or even a desire to relitigate the break up.

The problem is that, when they succumb to the moment and try to get back with their exes, it falls apart all over again. Either their ex doesn’t want them back and they’ve hurt themselves over a momentary impulse, or they do get back with their ex successfully… and realize that they’re no longer actually interested, and end up hurting someone who went into this in good faith.

Getting back to your letter: you say that you’ve gone through counseling and you understand yourself better. That’s excellent! Similarly, you’ve got more relationship experience under your belt  and you’re in a better place now than you were when you and your ex broke up. Again: this is great, and you should be proud of all of that.

But with all of that new self-knowledge and understanding, and the understandable regret for how you ended things, why are you thinking of reaching out now? Sure, your ex attending a graduate program at your university presents an opportunity; she’s going to be in general proximity to you and back in your life in some ways. However, if you feel bad about how you ended things and want to make amends, why have you not reached out before? I presume that you haven’t had these revelations within the last couple of days. Similarly, if you know that she’s been accepted to a graduate program at your university, that you’re in contact with her in some way. You’ve had opportunities to reach out before and say “Hey, I know this is out of the blue, but I wanted to apologize for how I ended our relationship.”

So why is it only now, now that she’ll be back in your city that you’re feeling the need to reach out? Is it honestly only to make amends? Or is reaching out to make amends the convenient way to try to rekindle things? Are you trying to make things right because you feel bad about how you treated her, or are you hoping that this is your opportunity for a second chance?

Don’t get me wrong: I’m not casting aspersions or doubting your sincerity and suggesting that you’re being manipulative. I’m sincerely asking you these things so that you ask yourself these questions. That’s going to make a big difference in how to approach things — and whether it’s a good idea to make the attempt in the first place.

There’re a lot of factors in play here, up to and including how you ended things and — importantly — how she felt and currently feels about your break up and you. If the break up was ugly and scarring, she may not want to hear from you, even if it’s because you’re trying to apologize and make amends. Part of making amends, after all, is to recognize when reaching out would just cause further harm or pain. And if she’s still hurt by the break-up, reaching out to make amends as an opportunity to try to get back together could be especially painful.

Now all that having been said: I don’t think that messaging her out of the blue is going to be the best course, regardless. If you two are still in regular contact, it might be different, but it sounds like you haven’t spoken to her since the break up. Assuming that you can answer the  questions and everything is a genuine desire to make amends and see where you two stand now… it would still be better to do this in person. As someone who’s patched things up with exes and came out the other side with renewed friendships, this is the sort of thing that’s best done face to face, if at all possible. And since you and she are attending the same university, the possibilities are there.

However, I would caution you against seeking her out to try to make this happen. What I would suggest instead is that you wait until your paths cross organically. This may not happen; universities can be pretty big places and if you’re in a graduate program, you’re usually sequestered in your own world. But if it does and you happen to bump into each other, you’ll be in a better place to gauge how she feels about seeing you. Is she cool with you, or is it uncomfortable and stilted? Is she happy to see you, or is it clear that she’s just being polite until she can leave? If — and it’s a mighty big if — it seems like she’s cool and you’re cool, you can propose meeting up some time. Or you can wait and see if she reaches out first and tries to reconnect.

If and when she says yes, then you have a better opportunity to say “I want to apologize for how I ended things, way back when. I handled everything badly and I know it hurt you, and I’m sorry.” After that — not before, after — you can maybe, possibly see if you and she can try again.

And keep in mind: she may be willing to see you and talk about things, but she may still not accept your apology and that’s fine. She isn’t required to, and you have to be willing to accept that. That doesn’t mean “try harder to earn her forgiveness” or “find some way to get her to see you’re sincere”. It means that you accept her feelings on the matter and leave her alone. If she changes her mind and wants to see you again… well, the ball’s in her court. She knows where and how to find you.

The most important thing however, is to take things — however they go — at her pace. She may need time to feel comfortable with meeting up with you, or to want to talk about how things ended. She may well also require time before she’s ready to talk about things going forward, whether platonic or otherwise. But if you honestly want to make things right, then that’s going to be part of the process.

It ain’t easy, and it certainly isn’t guaranteed. But those are the chances you take. You have to decide if it’s 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