DEAR DR. NERDLOVE: First of all, thank you for all your work, it’s really interesting and I’ve been kind of addicted to reading your articles since I found out about them!

I’m a 21 year old Computer Science student from Portugal and I don’t really have a specific question, but my romantic and sex life is pretty null right now, so I tought you could help.

I had my first relationship at my senior year at high-school four years ago and we broke up two years ago, and ever since, I haven’t had any romantic or physical connection with a woman. I still don’t know how it happened, because all the effort of how we got together was made by her, and now I feel like I don’t have any experience in charming a girl. I’m a very social anxious guy and I suffered a lot of rejections meanwhile and I hardly get any dates. I think this is because I can never keep it cool.

Every time I actually engage in an interesting conversation, I end up too attached to the girl to the point of always wanting to start a conversation whenever I’m bored or needy. I also tend to shift the conversation very quickly to be about feelings and personal stuff. This can cause them to see me only as a friend or even worse, stop talking to me, because I was creepy or needy. Either way, I never feel any signs of attraction and this is deepening the problem. This usually leads to me just being straight forward with them and getting rejected every single time. It’s hard for me to find a reason to why I feel like this with women, I consider myself a well rounded person, with hobbies, friends, etc…

Thanks for your time!

Anxious Anonymous

DEAR ANXIOUS ANONYMOUS: You have a very common problem, AA, but not quite in the way that you think. Yeah, that anxiety attack you have causes you to lose your cool, but that’s more of a symptom than a cause.

The issue is two-fold. The first is that you – like most socially anxious, awkward people – are empathic. In fact, you’re a little too empathic. You – like your socially anxious brothers and sisters – get really, reallyworried about what people are thinking, if you’re bothering them, etc. On the one hand, this is noble and considerate of you. On the other hand, it gets very awkward for everyone involved because now you’re radiating anxiety in every direction and people pick up on that. You’re busy imagining all those worst-case scenarios that start with your saying “hi” and end up with your face plastered all over social media with an alert about how you’re the creepiest creeper ever to creep.

The other issue is that you’re putting way too much importance on the woman you’re talking to. Now don’t get me wrong: I’m sure she’s amazing. However, she’s not the only amazing woman out there. Hell, she’s probably not the only amazing woman within a 500 ft radius of you. The problem is that you’re treating her as though she were the only chance you have to find a relationship for the remainder of your life. As a result: you get caught up in a cycle where you seriously over-invest in them – both for representing your Last Chance Ever but also for the validation they give you.

So what do you do?

Well to start with, you’re going to learn to calm yourself down in the moment. As I’ve said before: your brain takes it’s cues from your body. If you keep control of your body, you can control your mind. So the first thing you want to do is practice breathing techniques. When you’re feeling anxious, focus on your breath. Breath in slowly, to the count of four. Hold it for the count of three. Then breathe out again for another count of four. Repeat this over and over – just breathing in, holding it, and breathing out again. This will help slow down your nervous system and lower your heart rate; that, in turn, will help you calm down. You may worry that this may make you seem distracted or keep you from responding as quickly as you might feel like you should. It will – it takes practice until you can do this without having to concentrate – but this is actually a bonus. Forcing you to take your time means that you won’t just blurt out whatever comes to mind or make sudden and awkward conversational transitions. Taking time to pause before replying to what the other person has said will also have the bonus of making you seem more considerate and charismatic; you’ll come across as taking time to really think about what they said instead of just waiting for your turn to talk.

But that’s just the physical issues. You also need to work on the mental and emotional side of the issue. And the way you do that is simple: you have to start practicing being outcome independent. Part of why you get so anxious and lose your cool is because you treat each conversation as a sudden-death quicktime event, where if you don’t do everything perfectly, everything in your life will come crashing down around you. As a result: everything is huge. It is vital. You are on the cusp of ruining it all!

So instead of trying to impress this person or win them over, you’re going to take dating or attraction off the table. Your only concern is just having a fun conversation. That’s it. You don’t need to impress them. You don’t need them to like you for more than just the span of 10 to 15 minutes or so. Did you have fun talking to them? Did they have fun talking to you? Cool, mission accomplished. You can walk away with your head held high.

Learning to become outcome independent and letting a conversation just be a conversation is important because it turns off that fear of failure and any catastrophe that may come with it. By getting in the habit of just relaxing and enjoying a conversation, things will flow more effortlessly. You won’t be as worried about impressing her because you’ll be able to focus on just connecting with her as a person. You won’t be as panicked because the worst that happens is that you excuse yourself and move on; all that you’ve lost was 15 minutes that you would’ve otherwise spent browsing Reddit or Facebook or what-have-you.

So learn to calm yourself down and just let things be what they are. Don’t get hung up on needing everyone to like you or to impress every person you meet. Enjoy some pleasant conversation, maybe make a new friend or two and just let things be. This will help that well-rounded, appealing person in you to shine forth.

Good luck.

DEAR DR. NERDLOVE: So there’s this girl I’ve known for about 2 months, but have been talking to daily for over a month. The first date we went on, she asked me out.

We haven’t seen each other for over a month, because I’m a homebody and haven’t gotten around to thinking of a good date to go on with her. We still talk pretty much every day, and she even initiates conversations a lot of the time.

This past Friday, I messaged her on Facebook asking her what she was doing after work tonight. She said a friend of her’s was picking her up. I told her that I wanted to hang out with her because it’s been a while. She then replies back saying that she doesn’t know what she was going to get into with said friend, and would let me know. We kept on talking Friday night until her friend picked her up. She randomly messaged me at 3AM Saturday morning saying “My phone died.” I replied later that afternoon saying “That sucks. What are you up to?” – She didn’t reply until SUNDAY saying “Just working, what about you?”. I replied back saying “Same here. Working on this project.” Then I never got a response.

I really do like her. I felt like I could have put in more effort to hang out with her. It wasn’t like I was blowing her off, I was still talking to her, I just never really got around to asking her out. Well, I did invite her to a social group event Friday before last, that she said yes to, but that event had to cancel.

What’s strange is we were talking a lot up until this past weekend, now I feel like she completely wrote me off and I don’t know why. I really do like her, and I’d like to at least attempt to salvage what is left.

Initiate Recovery Mode

DEAR INITIATE RECOVERY MODE: Ok, couple of things.

First of all, for future reference: you don’t need to put a lot of effort into putting together “good dates”. Most dates are fairly simple affairs – you’re going and doing things that are fun together. Maybe that’s going to the zoo. Maybe that’s getting coffee and playing board games. Maybe it’s playing pool or seeing a comedy show or racing go-karts. Maybe it’s just a walk on a gorgeous day. Don’t let trying to find something “perfect” become the enemy of the “pretty good”.

Now as for what’s going on:

She’s not that interested in you, romantically. She clearly still digs you as a friend – and that speaks volumes to your connection together – but at the moment she’s not feeling it when it comes to going on a date. You can see it pretty clearly in her responses to you. As a general rule, when people are interested in someone, we tend to make definite plans with them. If we already have plans for a specific day, we’ll tend to try to find another time when we can get together. A “Well, I’ll have plans but we’ll see” is a pretty textbook example of a “soft no”; it’s a way of saying “nah, thanks” without being direct and risking hurting the other person’s feelings.

(It also doesn’t help when, during a conversation, you don’t give the other person anything to work with. “Same here, working on a project” doesn’t really spur a response, especially if the other person isn’t really motivated to keep up her end of things. Even a little humorous exaggeration -“trying to keep myself from dying of boredom as I pound this project into shape” – is more likely to prompt a response.)

The why of it is harder to discern. It certainly doesn’t help that you never asked her out on a second date; to most people, never suggesting another date is a pretty good indication that no, you’re not interested. As a result, she may well have assumed that you didn’t like her enough to ask her out again and ratcheted her interest down to “friend” instead of “potential snuggle-bunny”.

It could also be that she just wasn’t feeling it after the first date, so she wasn’t going to pound on your metaphorical door for a second.

Now, the question remains: can you salvage things with her?

Well… you can try. At this point, it’s more of a Hail Mary pass, than anything else; you’ll basically be throwing something out there against the odds and hoping that you’ll get lucky. Making it clear that you want to go on a date – not “hanging out” or “getting together” but a date – might make her realize that you’re actually interested in her. You might even explain that you took so long in getting back to her because you were trying to come up with a “good” date and just kind of got hung up on ideas instead of just asking her out.

But like I said: you’re probably just out of luck here. In the long run, it’s a better bet to chalk this up to a learning experience and not make the same mistakes next time.

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: Last year I separated from my wife. It was the first long term relationship I had ever been in, we were together for 10 years, and married for 8. We’d been living like we were married for almost the entire time we were together. Problems at her home when we first started going out spurred me to invite her to move in with me very early on in the relationship. Probably a bit too early, but that’s neither here nor there.

As the relationship progressed we Tic’d and Tock’d back and forth between an extremely loving and caring couple and an abuser/abused relationship with me as the abused. Nothing physical, but it was the classic emotional kind. Isolation, feelings of worthlessness, inadequacy in either in the bedroom and in the job field.

It took the intervention of someone I met at work and developed a strong –and likely unhealthy but that’s a different story– friendship with to really open my eyes to what was going on and make a choice of what I wanted. I was given an ultimatum and was forced to choose between my wife and my friend and I chose my wife. Because… that’s what you’re supposed to do, right? Well, saying goodbye to my friend was such an agony to do that it was what helped push me into making the decision to saying goodbye to my (now) ex-wife.

It’s been the better part of a year plus since this happened and I’ve gone on a grand total of One (1) date in that time. I was on OKCupid, Plenty of Fish, even Tinder. Entertainingly, the date I did go on was matched through Tinder but ended with coffee and someone I’m glad to call a friend, but nothing more.

The thing is… my heart’s just not into the dating scene. I’m 30, recently graduated with an Associate’s Degree back in December, and desperately underemployed for it. I speak to people on OKC, POF and other Dating sites but even when the possibility of a date is broached I just don’t “feel it.” I sigh, and try to politely decline. I’ve even matched up on Tinder a few times and even when a hookup is proposed I’ve got nothing. Zero interest on my part. I’m flattered when asked, I mean, I know what I look like; both in pictures and on paper.

So, I’m trying to get an outsider’s opinion on this. Am I in a slump? Is this something I should be looking into professionally? I’ve had a history of depression and the last two years of my marriage were goddamn miserable. I’ve read the site a lot, but to have just ZERO interest when a woman is basically saying, “Look, I want to hook up. You’re place or mine?” and my only response is, “I’m sorry, but this is not the D you’re looking for.”

Is there any way to work past this or is the answer a simple “Time heals all,”?

Not the D They’re Looking For

DEAR NOT THE D THEY’RE LOOKING FOR: While I don’t think it would hurt to talk to a counselor or a therapist to hash out some of the pain you’ve gone through, NTDTLF, you’re looking for problems where there really aren’t any. You’ve recently ended a very long-term, turbulent relationship… that’s going to take it’s toll on you. There’s going to be a period of adjustment – after all, you’ve just cut out a relationship that’s lasted for a decade. That’s going to have carved a groove in your brain. In a lot of ways, it’s almost like you’ve lost a limb and you’re going to need to adjust to doing things differently, from things as major as your daily routine to as seemingly minor as where you sleep in your bed. You’re going to have a lot of little things to unlearn that you’ll never even suspect had become part of your daily life until it was suddenly gone.

And then there’s the emotional toll that this can take on someone. You’ve been in an abusive relationshipand that’s going to leave wounds and scars and those take time to heal. To be sure: everybody handles abuse differently and there’s no one way to respond to an abusive relationship but frankly… it’s going to take a little time just to get back into emotional shape again.

I don’t think that you’re in a slump, I think your problem is that you’re trying to leap back in before you’re ready to date again. Yes, everyone recovers from breakups and heartbreak at different speeds and some people often start the getting-over process while they’re still with their partner but a year is awfully quick to try to push yourself back out there when you’re not feeling like you want to be out there. Maybe you feel like it’s time. Maybe you have well-meaning friends who’ve been telling you that you need to get back out there as quickly as possible or maybe they think that people need to be coupled off to be happy. But while getting under someone can be a great way to get over someone else, that’s not the only way to get over a break up… especially a relationship that was as turbulent as yours.

So do yourself a favor: take yourself back off the market. Suspend your accounts on OKCupid and Tinder. Spend some more time on you, with friends and family who’ve got your back and who’ll just be there for you while you take care of yourself. Just let yourself recover at your own pace and wait until you feel like you’re ready to date again – not when you “should” be but when you honestly feel the desire to do so.

Don’t worry about how long it will or won’t take; the dating scene will be there waiting for you when you’re ready to come back.

Good luck.

DEAR DR. NERDLOVE: I have been reading your book, New Game +, and I love it. I’m up to doing the approaches bit and I have got a bit of anxiety.

I love the idea of gradually desensitizing myself. Yesterday I asked 7 girls for the time like you suggested. I didn’t ask 20 people for the following reason (and this is my current sticking point):

I work in a smallish town just outside of London. I would love to do them at lunchtime but my biggest fear is for my colleagues at work finding out what I am doing and my employer finding out about it. That of it blows up and an interaction goes wrong and if it’s witnessed by my colleagues, my employer may think I am harassing girls. Even if an interaction doesn’t go wrong but it is witnessed by colleagues, they think I am asking weird questions.

Also I am worried about bumping into the same people if an interaction goes wrong.

Do you think this is a legitimate fear?

I am thinking about approaching girls in a different town or London where I can do it and practice anonymously. It’s a shame I can only do it on weekends.

What are your thoughts on this?

Thanks

Nervous Newbie

DEAR NERVOUS NEWBIE: You’re overthinking things, NN. If it’ll make you feel more comfortable and you’ve got the cash to do it, then by all means, practice regularly in London. But I don’t think it’s really necessary.

If you’re following my book, then all you’re doing right now is making some fairly innocuous approaches – you’re asking people for the time or for directions to some place nearby. If your colleagues think that asking a stranger for directions to Starbucks or the nearest Marks and Sparks is weird… well, that’s pretty much their damage, really. Can’t really help it if they assume that human interaction is inherently unusual. Even when you advance a little further, you’re just having a brief, polite conversation with someone before going on your way. That’s really it. As long as you’re not bothering people – trying to start conversations with people who’d rather not talk to anyone, for example – there really shouldn’t be any problems.

Similarly, unless your town is so small that everybody knows everyone else by sight if not by name, then odds are that the people you’re approaching will forget that you exist pretty much as soon as you leave their eye-line. Think of how many people you see during your daily commute to work and back. How many of them actually stand out in your mind, instead of being a non-descript, human shaped blur?  Trust me: people are more oblivious and self-involved than you realize. Unless you do something so significant or unusual, you’re going to return to being the background noise in their day-to-day lives.

Just remember: at this stage, all you’re doing is getting used to having brief, polite conversations with folks. This is How To Human practice, not making street approaches and trying to get phone numbers. There are times and places where that’s appropriate and the social contract allows for it. But that’s for later on. Right now, just work on being comfortable talking to folks.

Good luck.

DEAR DR. NERDLOVE: Your advice vibes well with a lot of others I read and take seriously, my question is simple, but it seems complex to me. I’ll make the story as short as possible.

I have feelings for a girl I’ve known for two years. The feelings mutual. She used to date a good friend of mine. About a year ago, they broke up. It seemed like they both moved on, she was dating a new guy, he moved in with his new girl.

5 months go by, she breaks it off with her new boyfriend. She and I have a talk over text, she invites me over to her place for drinks (around midnight), I decline the offer, counteroffer with Saturday evening at my place, she accepts.

Everything seemed good to go, two nights before the date my friend calls me up tells me he’s thinking about getting back together with her. I tell him he should do what feels right, he decides he’s going to. I decide it’s best to back-out of the situation, I should have explained why but I didn’t, it was obvious she felt rejected by me, which was not my intention. A month later they’re back together, now, every time I’m over there’s this huge amount of sexual tension between her and I.

She’s flirting, engaging me in conversation, touching me, making eye contact with me to the point where we’re staring at each other you get the idea. I TRIED to friend-zone this girl even though I have feelings for her, but its not working. So my question is this, would it be appropriate for me to sit down with her, tell her how I feel, and make it clear that I have no intention of betraying my friends trust? Or should I just keep my mouth shut and keep my distance, even though it doesn’t seems to be having any effect on her, she just comes onto me harder.

Before you tell me I shouldn’t talked to her or asked her over in the first place, me and my friends have a rule about dating each others ex-girlfriends which I followed to a T.

I Wish I Didn’t Like Jesse’s Girl

DEAR I WISH I DIDN’T LIKE JESSE’S GIRL: Before I go into my answer here, I want to take a moment to highlight your last sentence. You really didn’t do anything wrong about inviting this woman over.  She was clearly interested in a booty call with you. She was single. You were single. It’s all pretty much on the up and up. The fact that she’s your friend’s ex is kind of irrelevant, to be honest. Yes, she and your friend have history but – as I’ve said many times before – you don’t get to call dibs on someone. The fact that they’ve dated doesn’t mean that he gets to decide who is or isn’t allowed to see her. If he can’t handle the idea of someone he knows seeing her – especially a year after they’ve broken up – then that’s his problem. Not yours. Not hers. You’re both grown-ass adults. You get to decide what you want to do for yourselves.

As for what’s happening between you and her now that she’s with your buddy again? Assuming that she is indeed flirting with you and you’re not misreading the situation… use your words and tell her that you’d rather she stop flirting with you while she’s with him. If you want to give her a little extra wiggle room for plausible deniability, you don’t even have to be direct about it. Just say “Hey, I don’t know if I’m just reading too much into things, but I’m kind of getting a flirty vibe from you while you’re dating my friend, and it makes me a little uncomfortable. Maybe I’m wrong, but I’d appreciate it if we could have a little more distance while the two of you are together.” This gives you both room to save face and address the elephant in the room.

Plus, if and when the two of them break up again, then you’ll have left things open for the two of you to bang like a screen door in a hurricane.

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 had an interesting childhood, abusive father, bullied in school etc. which really hammered my self esteem. I basically bottled everything up for years until it all exploded. Ended up spiraling into depression, had a passive suicide attempt about 3 years ago and hit rock bottom really. The good news, since then I’ve had 2 spells of counseling and my mental health is now much better. I’ve also worked quite a bit on myself, to the point where I’ve come from never having a date to having a couple of short relationships, couple of casual things and I’ve improved immensely in that part of my life. This is way more success than I ever thought I’d have.

The thing that’s inspired me to write in today is that even though I can see how far I’ve come and all I’ve achieved, I still find everything absolutely, painfully difficult. Socializing exhausts me in general, but especially in bars and clubs. I always seem to be on guard and frankly it’s all wearing me down. There is still this block I have mentally, where I’m so scared of getting hurt again or opening up that I can’t really just let myself go and make the moves I want to, or I shut down interactions/ relationships that could go somewhere due to fear basically. I’m also incredibly nervous about doing anything that would jeopardize my mental health. I left my last job because it was causing me to slide again and I don’t want to risk ever getting near to where I was 3 years ago.

Another thing that’s laying it on right now is that I’m currently traveling. A couple of my friends are absolutely amazing with women, they make it look ridiculously easy and go from one hot girl to the next like they get handed out with the cereal. They are great guys who absolutely deserve their success and I’m happy for them, but it just highlights to me that even after all this work I’ve done I’m still no better than bang average on a good day at all of this. This is what is getting me down. I’ve read all the articles you’ve written about staying internally validated and not comparing yourself to others and it’s all good advice, but I’m struggling to keep everything focused on the right things, which ends up with me taking nut shots to my self-esteem over the frustration.

I’m still young, mid 20s in decent health and everything, so I know I have the time, but it’s just so draining to actually realize how far I’ve still got to go after all this work. My motivation to keep going with the whole self improvement thing is waning, I’ve stopped approaching, don’t do speed dating or anything else that I had success with. I went on a couple of dates with this girl 2 months or so ago and just had no emotional energy left to give. I just see it all as a grind and I struggling to deal with it at the moment. I know you went through similar sorts of challenges back in your “bad old days”, so any advice you could give would be hugely appreciated. How would you recommend I get through this?

Thanks

Tired of The Grind

DEAR TIRED OF THE GRIND: First of all, ToTG: congratulations on all the work you’ve put into your mental and emotional health, and all the progress you’ve made. That takes a lot of grit and courage, and you should be proud of just how far you’ve come.

In fact… that’s part of what I want to talk to you about. See, you’re doing one of the things that I used to do back in my bad old days: you’re so focused like a laser on the end goal – being able to get women like your buddies – that you’re missing just how much progress you’ve made. The problem with what you’re doing is that you’re working under the assumption that you and your friends started at the same place and the fact that you’re not doing as well as them means something’s wrong with you. But that’s not it. That’s not it at all. You didn’t start at the starting line; you had to sneak your way past guards, climb over walls and through air ducts just to get into the goddamn arena, never mind into the race itself. 

But here’s the thing: you got there! You made it past all of those hurdles, things that would make most other people say “ this noise” and turn around, and got your ass into the game. Yeah, you’re not at the same point as people who had some advantages you didn’t… but they didn’t have to fight the way you did or as hard as you did. So you need to take a moment and recognize that you’ve fought long and hard to get where you are and that is goddamn amazing. You’re not some third-string bench-warmer, you’re Rudy, man.

Of course, all of this means that you’re going to have some scars. I mean, c’mon: you’ve been through the fires of hell and you’ve got the ashes to prove it. But that block you’re dealing with right now isn’t fear, it’s the anticipation of fear. You’re so worried about the feeling of “Oh god does this mean it’s going to happen again” that you’re trying to avoid anything that might trigger that fear… including the things that you long for. And that’s understandable. That part of what makes us human. But the fear is an illusion. It’s a phantom. It’s the exaggerated, funhouse mirror version of reality. The fear is honestly worse than the reality.

Right now, you’re spending a lot of your energy trying to avoid your fears – more energy than it would actually take to confront them, in fact. You just keep convincing yourself that you’re going to lose, that you are inevitably going to fail, so there’s no point in trying. Small wonder you’re drained; you’re letting that fear sap everything from you, without even taking the little victories that tell you that you’ve got far more going for you than you realize.

The sooner you learn how to grapple with that fear and push through it, the sooner you’ll realize you’re further along than you believe you are.

And the easiest way to deal with that fear? Plan for failure. Expect failure. Because you know what? Failure’s gonna happen. A lot. To everyone. Even your buddies, who attract women the way cheese attracts mice, fail. You just don’t notice it because you’re paying too much attention to their successes. But success doesn’t teach you anything. A lot of times success is just luck – or you end up taking the wrong lessons from those successes. When a plane comes back from a mission shot full of holes, you don’t patch those holes and assume you fixed the problem; those are clearly places where it could get shot up and still make it. You want to pay attention to the places where getting shot full of holes brought down the plane and work on those areas.

So it is with failure. Failure teaches you valuable lessons. You learn to recognize what went wrong and how to avoid it next time. You start to learn your real strengths and weaknesses, not the ones you think you have. And the most important lesson you learn is this: failure isn’t fatal. You can mess up – badly, even – and still survive. You may not get with that one woman… but you can pick yourself up, dust yourself off and try again with someone else. 

Pain’s inevitable, my dude. Nobody can avoid getting hurt. But while pain may be inevitable, suffering is optional. And you suffer far more from trying to avoid pain than you do learning how to take the hits, roll with them and pop back up again because you’ve given up on even the chance of success.

These are choices you’re making, my dude. You’re choosing to believe that you will fail and it will break you. It won’t. You’re stronger than that. Yeah, you’ll fail. It’s part of the learning process. Everyone fails. But when you learn from those failures, when you dare to push yourself  back up to your feet again? That’s when you win.

You have to believe that you can survive. You hold that power in your hands.

You can win if you dare.

You’ve got this.

Good luck.

DEAR DR. NERDLOVE: I have an ethical question.

The short version: a decade ago I met someone, we talked online a lot, those chats got steamy, and I saved them. Now I’m debating if I should get rid of those saved chats.

Long version: when I met J, I was in a terrible place: 25-year-old virgin with body image issues and depression, under-employed, and self-harming. J (who is gender-neutral) essentially made helping me a short project, out of the goodness of their heart, and we had what I call a “two-month-long one-night stand”. Since we lived in different cities, we communicated online only, until J invited me to their city for a weekend of sex and sex ed. This did wonders for my confidence, and our friendship helped me stop cutting. (Nine years clean!) A critical step in the process came when J laid out for me, in considerable detail, what they would do in bed with me once we were in the same place. Until that moment I had not really believed I was physically attractive to anyone. I saved that chat so I could look at it again later and remind myself it actually happened, and I saved other (sometimes steamy, usually very personal) chats as well.

Ever since then, we have been supportive friends. We don’t talk all the time, but we always know the other person will always be there. We’ve watched each other go through all sorts of relationship ups and downs. When we’re both single (and only then) we flirt, though this hasn’t happened in a while and nothing comes of it.

J’s in a relationship “up” — getting married to a truly marvelous person — and I’m in a relationship “neutral” — single for a year. The wedding has made me think about those saved chats. I look at them maybe once or twice a year, if that, but while they aren’t the same level as nudes, they are they are personal and intimate, and critically I don’t think J knows I have them, so it feels a little non-consensual. So on the one hand, it seems like the ethical thing to delete them.

On the other hand, I’m a very history-oriented person, so deleting those chats would be like deleting all evidence of a key turning point in my life. Also, while my depression is much more under control, it’s never gone — so having evidence of J’s validation is sometimes very nice.

On the third hand, I know I’m still attracted to J, so I’m a little suspicious of my judgment on this.

What do you recommend? Delete the sexy chats, or preserve the historical artifacts?

Ethical Historian

DEAR ETHICAL HISTORIAN:  there’s a lot of debate about that to do about the artifacts of our past relationships. Almost all of us tend to have keepsakes of our happier relationships; letters, photos, little trinkets that remind us of the good times we had. Most of the time, these are fairly harmless bits of nostalgia that we can take out, enjoy that warm hit from times past, then put ’em back and call it good. Now there are often people who feel threatened by the evidence of past relationships – the story of the Jealous Girlfriend is a well-worn routine from the early days of the Pick Up Artist scene – but for the most part, these are just reminders of days gone by. Getting rid of them just because the relationship ended smacks of trying to pretend the relationship never happened, an emotional damnatio memoriae that ultimately denies how we became the people we are today.

But some of those mementos can be of a sexual nature, and that’s where things get tricky. We live in a culture and society that’s profoundly sex-negative, and sees sexual expression as something shameful and degrading, even when it’s in the context of a committed, monogamous relationship. And in the aftermath of a break-up, the question of “what should we do about with these mementos” gets thorny. On the one hand, there are those who insist that they should be destroyed; after all, you (so the theory goes) no longer have that person’s consent to see their naked bodies. But at the same time, if you take this argument to its logical extension, then you’re no longer allowed to remember them or the way their skin felt or their hair smelled because hey that relationship’s over. On the other hand, there are those who will say that these were given consensually between two partners and like all gifts, there’s no obligation to return them later. But then there’s the fact that they were given under a specific context; if the relationship ended badly, those relationship artifacts can go from being mementos to weapons that can be used against the giver.

And sometimes, those memories can be weaponized by a third party. In this day and age, securing those particular relics is difficult. Cloud storage sites get hacked, computer repair services regularly steal people’s nudes from their hard drives and sexy files of unsuspecting innocents get shared far and wide. One only need look at The Fappening or boards on Reddit, 4chan, 8chan and elsewhere that are dedicated to sharing “found” nude images. Even purely physical keepsakes can get out into the wild; the infamous Pamela Anderson and Paris Hilton sex tapes were on physical media, not digital storage.

These are all issues that’ve become part of the modern dating landscape. If we share those sides of ourselves with our partners – as many, many people do – there’s the chance that they won’t just stay with our partners.

Now in your case, EH, the odds of some spicy chat logs getting out and causing problems is low. Not zero, but pretty darn low. So the bigger issue here is: why are you holding on to them? As you say: you still have some feelings for J. Is this a way of holding onto the relationship, instead of letting it be part of your past? There’s nothing wrong with the occasional naughty trip down memory lane, but if this is a way of keeping the hope alive, even as they’re getting married… well, that’s not healthy. It may be good to interrogate your feelings on this and see if your desire to keep that validation and evidence of your past is exactly that, or the fig-leaf you use to justify keeping them.

The other question involves the ethics of having them in the first place. While it’s generally a good rule of thumb to assume that anything you send to another person is likely stored and archived somewhere, a lot of folks tend to assume that hot chats and sexting conversations are lost to the ether; hell, that’s part of the whole point of services like Snapchat. As far as violations of trust go, it’s pretty far down the list, but some folks might still feel weird about knowing that those records exist.

So with all of this in mind, here’s my guiding principle when it comes to things like nudes and sexy pics from past relationships: if you’re on good terms with your ex, ask what they’d prefer you do. Of course, in your case, EH, first you’re going to have to explain that you have them in the first place. Which is gonna be awkward. But honestly? I suspect this will cause more amusement than consternation.

Some people are cool with their exes – especially ones they’re still friendly with – keeping the pics. After all, just because the relationship ended doesn’t mean that you now hate that person and want to retcon the relationship into having never happened. Others may prefer that you’d delete them, if only to keep them from ending up on dodgy blogs and subreddits.

So, you don’t need to explain about how they give you validation or that they’re an artifact of your past. Just say “Hey, turns out I have logs of some of the chat sessions we had, would you prefer I delete them or is it ok if I save them?” and let them have the final say.

And as a general rule: if you aren’t in contact with your ex – it was a bad break-up, you never want to hear from them again or vice-versa – go ahead and securely delete them. It’s better all around to err on the side of “get rid of them” than it is to have trouble down the line.

Good luck.

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