DEAR DR. NERDLOVE: I’ve spent about twelve years avoiding dating throughout my twenties and thirties. I initially thought it was just about a bad breakup but have come to realize I’ve had a lot of neglect growing up that made it difficult for me to really trust myself, let alone others. I’ve done all the excuses – women are happier without men in their lives, I’m worthless and garbage, I need my own space, I’m not ready, I’m too ugly, etc. But I think I have exhausted all of them now. Except the big one.

I’m currently doing the work now, going to a therapist, getting back in shape, reconnecting with hobbies and friends. A lot of this has been just because I don’t want to feel numb and that I’m a worthless all the time, more than anything.

So I want to try dating again and see if I can find someone, I think I have the right approach – I do want to like, validate and support someone as much as I want to feel validated (maybe more, I’m working on self-compassion!). But how do I know when I have done enough? Should I just try anyway? I’m still in a raw phase when it comes to therapy, I’ve had one or two breakthroughs but get the sense there are layers to this onion.

Ready. Unsteady. Go?

DEAR READY, UNSTEADY GO: Quick question before we dive into this, RUG: have you talked to your therapist about the possibility that you’re dealing with chronic depression? Mentioning that you feel numb and worthless all the time struck a chord for me – numbness and just feeling like there’s no point to anything is one of the most common ways that depression presents itself.

If you haven’t, it may be worth your time to do so; depression is often a matter of your brain’s chemistry and requires medication to manage, in addition to various forms of talk therapy.

The other thing I would ask is: have you talked to them about your attachment style or your emotional wounds? You mention a lot of neglect growing up; that can often lead to people feeling like they don’t deserve love and affection, which can also get tangled up with feelings of worthlessness or being deficient in some way. Addressing those issues can go a long way towards helping you feel empowered to actually seek out love without sabotaging yourself in the process.

But to answer your overarching question… well, I hate to tell you this but I think if you’re hoping for a moment where you feel a “click” or have this sudden burst of light and a “Level Up” icon appear, you’re going to be waiting a long, long time.

Those moments of sudden shattering insight or all the pieces falling into place like Agent Kujan suddenly realizing that Verbal Kint was Keyser Soze all along make for great moments in fiction, but almost never happen in real life. Personal development and therapy tends to be more of a gradual understanding and feeling of improvement than reaching some point where suddenly everything makes sense. Sometimes it’s like realizing that you’ve made progress simply because you’re suddenly aware of the absence of something that you’ve felt for so long that it’s been like background noise for you. Other times, it’s a willingness to say “well, I feel like I’m in a place where I can give this a shot” and giving it a sincere try even if you aren’t completely sure.

The more important thing is that you don’t need to be in perfect mental or emotional shape in order to date; you just need to be in good working order. Think of it like a car; you don’t necessarily need your car to be in mint condition, like it just came off the assembly line. A car can have its quirks – the upholstery can be 40% duct tape by volume, the fabric on the roof may be coming down it may judder and shake when coming to a stop, or it may make weird noises when you turn the wheel past a certain point, you may have to turn the key in the ignition a particular way to get the engine to start – but it’s still safe to drive and will get you where you need to go.

So, this becomes the question you need to ask yourself: are you in generally good working order at this point? You’re the best authority in your overall state of mental and emotional well-being after all; you’re the only one who can answer that question. Do you feel like you’re sincerely in a place where you can date?

Keep in mind: dating means more than just finding someone to love, it also means dealing with disappointments, frustrations and a willingness to risk and face rejection. You mention that you’re still in a raw phase with your therapy; how does that feel and how is it affecting your mood, your sense of self-worth and happiness? Are you ready to deal with the various slings and arrows that are part and parcel of finding someone to love without falling to pieces? Are you ready to handle the times when, say, someone you’re into isn’t necessarily feeling it? Or is this likely to shred your self-esteem into bits and kick your peace of mind into the storm drain?

It’s important that you answer this honestly. You don’t need to be 100% certain that you are, and having some hesitancy doesn’t automatically mean you’re not. If you wait until things are “perfect” or you get some sign from on high… well, you’re going to be waiting for a very, very long time because there’s never going to be a “perfect” time. If you feel like either you’re not in a place where you can handle rejection or disappointment or pushback in a healthy and productive manner, or you don’t know if you’ll be able to be a good partner for someone without doing harm to yourself? Then there’s no shame in saying “ok, I need to give it a little more time”. On the other hand, if you feel like that car I talked about – quirky, maybe a little dinged up but generally functional and passed basic inspection? You can give it a shot and see how things go. You may – and I stress may – want to focus on casual dating at first, to get a feel for where you are and get your metaphorical sea-legs. But as you get a better sense of how you’re feeling and how things are affecting you, you’ll have a better gauge as to whether you’re ready to pursue something more serious, with more intentionality.

And don’t forget: deciding that you’re ready to start dating or deciding you’re not ready just yet isn’t a permanent decision. You’re always welcome to say “ok, maybe I need a little more time” and take yourself off the market for a bit, or to say “OK, last time out kinda sucked, but I’m ready to try again”.

There are no guarantees in life, and especially when other people – ones with free will and agency – are involved. It can be scary. It can be hard, and there will be times – even if you’re in the peak of mental and emotional health – where it can make you want to climb the walls with frustration or despair. But as frightening, frustrating or emotionally draining as dating can be… it can also be amazing, affirming and even life-changing at times. You’re the only one who can say whether you’re ready or not.  

Nobody ever said it would be easy. They just said it would be 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’m a middle-aged guy who’s always had lousy luck with dating. After I exited my last relationship because her biological clock turned the pressure up to 11, I decided to take some time out and do a little work on finding myself. That lasted longer than I expected due to COVID.

But what I did find was, in doing some reading on asexuality, that the concept really resonated with me and I am probably somewhere under the ace umbrella. Where, I’m not exactly sure. But it’s had me second-guessing a lot of my previous relationships. I have never had any luck finding dates outside of online dating, and with most of those, we’d spend some time chatting online before meeting in person…only for me to feel like things went well and for her to spend the next week not responding to my messages until she gave me the next “it’s not you it’s me” speech.

So, looking back, now I’m wondering if a lack of sexual attraction on my part meant that I wasn’t projecting enough interest. Was I spending too much time looking at her face and not elsewhere? Was my body language not showing that I was a little worked up? Was it that I didn’t go for a kiss or a hug–or a bedroom–at the end of the date?

And now that I’m ready to consider dating again, what do I do with any of that, plus my self-discovery? I’m not exactly thrilled about online dating, but it’s the only thing that’s worked for me. Meeting people organically, or being introduced by friends, hasn’t gotten me anywhere. My biggest problem with online dating is that it seems to be an all-or-nothing shot: if there’s no physical chemistry right away, it feels like they check me off the list and move on to the next. Meanwhile, I want a friendship to build up over time and see where that leads romantically. And, honestly, even if things don’t work out romantically (I am almost definitely sure I’m not aro along with ace!), I’d still like to stay friends, but that has never happened either. Do I lead off with “I’m ace” and then have to deliver the explanation of what that means? Do I have to learn how to give off the right signals of interest? Do I just keep being me and hope I finally find someone who likes that, even though that has been a frustratingly unsuccessful journey?

—Ace of Diamonds, Not Hearts

DEAR ACE OF DIAMONDS, NOT HEARTS: Hey, congrats on learning more about yourself and how you work, ADNH; that’s a pretty big step, especially when you’re hitting your 40s and older.

So what does this mean for your love life going forward? Well, let’s start with something obvious: without actively reviewing the footage of you on these dates, it’s going to be next to impossible to say what, if anything, didn’t go right. And I do mean “if anything”; sometimes it really is just down to “it’s possible to make no mistakes and still lose”, especially when it comes to online dating. One of the things about meeting people on the apps that’s just baked into the whole experience is that there will be people who seem to be great on paper, but who lack that x-factor that needs to be there for you two to be a good match. False positives and first dates to nowhere are, unfortunately, just part of the process.

It’s certainly possible that your lack of sexual attraction meant that you were either not making the best case for yourself or showing any real interest in the other person. It’s also entirely possible that the vibe you were giving off was more platonic or friendly than “potential partner”. Or it could just be you had a string of bad luck through no fault of your own.

I think, however, the more important thing is to recognize that you were dating at a time when you didn’t know what you now know about yourself, and that’s a pretty significant difference. This is why I think focusing on what may or may not have gone wrong in the past isn’t as important as figuring out what to do moving forward.

So, the first thing I think you should do – if you haven’t already – is start doing a little due diligence on being asexual. Asexuality is less of a spectrum as much as it is a multi-axis graph, with a number of different variations of how it works for different people. Some folks don’t experience sexual attraction at all. Some are actively repulsed by the idea of sex or sexual contact. Some experience sexual desire, but only rarely or only after they have a meaningful emotional connection with the other person. Others experience arousal but aren’t interested in sex with another person, and still others could take or leave it.

One of the best resources out there for ace people – especially people for whom asexuality is either a new concept or a new way of understanding themselves – is the Asexuality Visibility and Education Network. I’d suggest you should do some exploring of the material and resources they have, if only so you have a better understanding of what being ace means. It’s a lot easier to explain to others when you’ve got a pretty solid idea of what it means for you. Educating yourself on the topic will make it easier for you to communicate it to other folks who, like you, may not have realized at first that it was even A Thing.  

Now, when it comes to dating when you’re ace, there’re a few things to consider. The first is fairly obvious: most people you meet are going to expect a relationship to have a sexual component to it. If sex is not going to be on the table in a relationship with you, that’s something folks should know fairly early on. Letting them opt out early on – possibly before your first date, even – means that neither of you will be wasting time with someone who’s fundamentally incompatible. After all, the last thing you want is to get emotionally invested in someone who is going to want something that you can’t give and vice versa.

Functionally speaking, this means disclosing early. You are going to want to make sure that folks who might want someone just like you can find you, after all, while allowing the folks who aren’t able to rock with that to peace out and move on.

Some dating apps have options in their profiles where you can define your sexuality – not just as gay, straight or bi/pan, but asexual, demisexual, hetero or homo-romantic and so on. This gives folks the option to filter you out of their searches entirely. But even so, I would make it clear in your profile that you’re asexual – and I’d recommend saying “asexual” and not just “ace”; most people aren’t going to know the slang. However, I’d recommend that you also make it clear what you are up for – cuddling, physical but non-sexual intimacy, and so on – rather than just “there will be no sex, ever”. It’s better, in general, to focus on what you do offer, so people have an understanding what is actually on the table. Otherwise you risk letting them make assumptions about you that may well not be accurate.

However, while online dating can be convenient, you aren’t wrong that the modern apps encourage an expectation of nigh-instantaneous connection. That’s hard under the best of circumstances, but even more so when the physical chemistry may not be there even if the emotional chemistry is. And since you mention that you want more of a slow burn – going from friends to (nonsexual) lovers – I think what would work best for you is what I call “dating slow”. That is, rather than taking the all-or-nothing approach on dating apps, you should focus more on simply being social and meeting people organically without necessarily looking for dates.

One of the benefits of taking a slow approach to dating is how it lines up with your ideal relationship progression. By being social and focusing on a platonic connection, you’re better able to get to know folks over time. This not only takes the pressure off trying to turn every interaction into a love match, but it also plays to your advantage. The more we get to know a person, the more their uniqueness makes them special to us; we literally find people more attractive as we get to know and like them. This also means you have more of a chance to see if they’re someone who’d be right for you; not only do you have the commonalities and shared values and interests you’d need for a relationship, but are they someone who can rock with a relationship where sexual intimacy simply isn’t a priority?

In these cases, you may get to a point with folks where you’re ready to ask them out on a date. In those cases, if being ace hasn’t come up, you should mention it – if not before the date, but at least at some point on the date. And, much with dating profiles, you should feel comfortable with explaining how this works for you and what you are and aren’t up for. Yeah, it means you risk people noping out, but this really is for the best. It’s far better to focus on the folks who are affirmatively and actively up for this sort of connection with you than to find out they aren’t three or four dates in.

When you do talk about being ace, however, you want to make sure that you’re not rolling this out like you’re the victim of a generational curse or you’re confessing some deep, dark secret about yourself. Being asexual is neither positive nor negative; it’s just a fact about you, like being right or left-handed. If you roll it out like something you have to apologize for, you’re priming them to reject you out of hand. After all, if you think it’s something shameful, why would they want to explore a relationship with you? Conveying it as “here’s who I am, here’s a fact of how I work” helps set the tone that this is just part of what makes you, you. It also serves as a filter for determining who may or may not be a good match. When you tell someone you’re asexual, you’re telling them a single fact about you. How they respond to that fact, however, will tell you a lot about what you need to know about them.

This, incidentally, is where visiting AVEN and learning more about asexuality can come in handy; it’ll give you an idea of how to communicate this to other people in a way that they can understand.

Now, a thing that you’re going to need to consider is how much traditional aspects of a relationship are going to matter to you. The fact that most people out there are allosexual – that is, they experience sexual attraction and an interest in sex with other people – doesn’t automatically mean that your prospects are limited to your fellow asexuals. It’s certainly possible for an ace person to have a relationship with an allosexual person. But making a relationship work with someone who is allo is going to require some compromise on your part as well as theirs.

Would you, for example, be willing to have some form of maintenance sex, where you may not necessarily be into it, but you’re willing to participate for your partner’s gratification? This may, for example, mean penetration, or it may mean providing a masturbatory assist – using sex toys on them or helping them out while they masturbate.

Alternately, are you willing to consider an ethically non-monogamous relationship, where your partner would have the option to get their sexual needs met outside of their relationship with you? Or is the idea of your partner having sex with another person going to sandpaper your nerves and leave you feeling raw and anxious? You don’t necessarily need to have a fully polyamorous relationship, where you both have multiple romantic connections, but allowing your partner to have sex outside of their relationship with you might be the difference between someone who’s willing to give it a try with you and just not feeling compatible.

If that’s something you think you could be ok with, I’d recommend doing some research into poly and open relationships and how to make those work. I’d recommend checking out Opening Up by Tristan Taormino, The Ethical Slut by Janet Hardey and Dossie Easton and Building Open Relationships by Dr. Liz Powell as a starting point.

(Full disclosure: Dr. Powell is a friend of mine and they’ve guest-written columns for me before.)

Mechanically speaking: you don’t want to learn to send signs of sexual interest, simply because you don’t want to give people the wrong impression. You should, however, work on your flirting and talking to folks, and being willing to express interest in them. You may have to rely on your words more than others, especially if you’re not necessarily comfortable with physical contact, but you do want the people you like to know that you like them as more than friends. Even if sex isn’t on the table, love is, and if someone doesn’t know you’re down for romance, they’re going to reasonably assume that you don’t like them that way.

But before we worry too much about that, you should focus more on understanding yourself. Do your research – AVEN has a lot of resources and links to other places – and figure out how you roll. The better you understand yourself, the more you’ll be able to find your path going forward.

I know that feels like I’ve given you some serious homework to finish before you start dating but I promise you: investing the time now is going to make the rest a lot smoother and more intuitive for you.

You’ve learned some important facts about yourself and hopefully that understanding helps clear up a lot of questions you had about yourself. Now it’s time to take that understanding a little further, in a way that’ll empower you to date in a way that makes sense for you and plays to your strengths, instead of trying to make it work in a way that was poorly suited for you.

You’ve got this.

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: For 6 months, a guy coworker and I have what seemed to be mutual attraction. He would regularly check me out, engage in intense eye contact, lean in, act really nervous when around me, looked surprised when talking to me – a bit like a deer in headlights, stutter a little and then recollect his thoughts. He’s super confident with other girls and guys, but not with me. He acts serious but flirty.

Anyway, I like him so I wrote to him back in January to say I was attracted to him. I didn’t hear anything, so thought I had got everything wrong. Then last week after a meeting he says he got my message and was sorry because he’d only just seen it and that he rarely checks that account.

I was shocked as it had been so long and I told him yes what I had written was true and he asked me didn’t I think it was strange that he didn’t reply to which I said I thought he didn’t care.

Anyway, he then said he had a partner. He didn’t say anything more. I have since found out he has had his girlfriend since January, but I believe he has been flirting with me a lot during that time. I get he has a girlfriend, but I’m also confused, as it seemed like he did like me, so what gives?

I kind of felt like he led me on to some degree. Up to two weeks ago, he was still showing signs of interest, he would regularly set up one to one meetings with me (when we are no in the same teams), linger to have a longer conversation and act a bit odd when I talk to another guy coworker.

Last thing I want is to come between him and his girlfriend. I guess I’m just confused as to why he even bothered with me. Now I also feel like it’s a bit awkward at work, like we say hi to one another and that’s it. We were friends before, but it was obviously more relaxed. Now it feels tense. Can you advise what happened here and why a guy would act like this?

Perplexed And Perturbed

DEAR PERPLEXED AND PERTURBED: The principle of parsimony – what is often called “Occam’s Razor” – states that when confronted with multiple possible hypothesis, you should select the one that requires the fewest assumptions, as this is the one that’s most likely to be correct. While this is more of a guide than a law or a mandate, it is useful when dealing with situations like yours, where there seems to be multiple possible explanations.

In this case, there are two possible hypothesis that stand out as requiring the fewest assumptions to be true: that he wasn’t flirting, he was just being friendly and what you were seeing as flirting was just him being him; or he’s the sort of person who’s just flirty but doesn’t necessarily mean anything by it.

Both of these are equally likely; people are notoriously bad at telling when someone is or isn’t flirting with them, especially if the other person is attractive. It’s very easy to let d--kful or c--tful thinking turn friendliness into flirtation, simply because the person wants the other to be flirting. There are also people who are just flirty because that’s how they roll and because flirting is fun. They are flirting without intent of following up on it, or expecting more than just the inherent fun of a flirty conversation.

Is it possible that he’s into you despite his having a partner? Sure; it’s hardly unknown for folks in relationships to be attracted to other people. People get crushes. And as I’ve said many times before: having a crush doesn’t mean anything other than “this person does it for you”. But was/is he leading you on? I highly doubt it, frankly.  Remember what I said about “Occam’s Razor”? Well, there’s a related guide called “Hanlon’s Razor” that states “never attribute to malice what can be equally explained by ignorance.” While it’s certainly possible that he’s the sort of person who gets his jollies by backburner-ing women or giving them just enough attention to keep them on the hook, that usually entails more than just “having conversations at work”

it sounds like you’re reading more into things than are actually there. That includes the tension, by the way; I suspect that it’s mostly coming from you and the way you’re feeling is affecting how you behave with him, which is going to affect how he responds.

As it is, I think the simplest answer really is “there’s nothing here”. Seeing as how he a) “didn’t see” that message for damn near six months, b) told you he has a partner and c) has never made any move that wasn’t “talking to you at work”, I think it’s safe to say that you were misreading things. And if you weren’t and he did have a crush… well, that’s a distinction without a difference, because it seems pretty clear that he has no intention of acting on it.

So, you may as well just work under the assumption that this was all a wacky misunderstanding. Allow yourself to feel silly about it, mentally roll your eyes at him over it and just let it go. I think you’ll find the friendship comes back a lot more easily when you do.

Good luck.

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