DEAR DR. NERDLOVE: I am a 45-year-old single woman, also a mom of an elementary school child. I’m pretty good looking, fit, I think I’m smart and funny. I have close relationships with friends and family, and don’t often feel lonely (I’m an introvert).

I honestly think I could be contentedly single forever, and that might be my fate.

However, it saddens me that I never found a person who loved me in that way. It seems… unfair. I’m no better or worse than any of my friends who found love.

While I am aware that I can certainly “get back out there” if I wanted, my concern is that the idea of dating fills me with dread. I dated before and even after I had my child and had some good times and some not so good. But it was never a joyful experience.

I don’t relate well to men I don’t know at first (I guess I’m shy, you could say). Plus, dating is time consuming, and I’d often rather do anything else then spend a week or more texting, then arranging a date, then going out and having the date.

And feeling rejected on the rare occasions I’ve felt connection, hurts more than I think it’s worth.

So, the larger winning part of me is content to swear off dating and the possibility of romantic love; I’ll choose to find ways to be happy.

But I guess there is still a piece of me that must want a partner, otherwise I wouldn’t occasionally wonder if I should be dating or wondering if there really is someone out there that I’m supposed to meet someday or wondering why I’m a person who wasn’t destined for romantic love.

Do you have any insights for me?

Still Single After All These Years

DEAR STILL SINGLE AFTER ALL THESE YARS: Let’s start off with something obvious, SSAATY: you are already doing what I tell people they should do if they want to be content whether they’re coupled up or single and that’s awesome. A good life with friends, passions and interests and having your needs met for companionship (and solitude when you need it) is something we should all strive for, regardless of our relationship status.

Now you, as many people who are in that situation, have found that this doesn’t mean that you don’t necessarily want a lover or a life partner; it just means that you have a good life whether you have one or not. And that matters, because it helps keep things in perspective: having someone to share that life with is an enhancement, not a necessity for happiness or contentment or satisfaction.

But here’s the thing about love that I think you need to remember: it’s not about deservedness or fairness. Love isn’t a reward granted by the universe to people who meet certain standards or tick particular boxes. It is, to a certain extent, a matter of probability – a matter of right person, right place and right time all coming together in a particular way. We just happen to take it very personally.

Is it your fate to be single for the rest of your life? Maybe. Or it might not be. Always in motion, the future is, and it’s impossible to say for certainty. You could be hit by a meteorite tomorrow. Or you could meet the love of your life when you’re both 70 and complaining about the quality of the Sunday brunch in your retirement community. Or anything in between. Nobody can say.

What I can say is that if you want love, you don’t have to be treat finding it like you’re planning an expedition to the Congo to find the Mokele-Mbembe.  I mean, you can put yourself out there if you really want. You can get on the dating apps, sign up for the single’s run clubs that’re starting to take off, go to speed-dating events or start hitting up cocktail lounges and flirt with strangers if you think it might be fun. But it sounds like you don’t, and that’s fine. That’s not the only way to meet people, especially considering that you know you’re someone who tends to be a slow burn.

Instead, what I would suggest is to just… live your life. But to live it in a way that makes it more likely for you to meet people who you would want to date.

One of the (many, many) reasons why folks often get frustrated with dating is because they treat it like a race, or like you’re interviewing candidates to fill a role. They get hung up on the end point – having A Partner – and so the outcome takes on outsized importance. They have turned Finding Someone into something that becomes more significant than the eventual someone and that can be corrosive to the soul. Yeah, we’ve all heard the cliché of “gotta kiss a lot of frogs to find a prince”, but that still means you’re out in the swamp, planting your lips on a bunch of amphibians. Unless you’re a MILF (Man, I Really Love Frogs), the shine is gonna wear off pretty quickly.

This is why I tell people that sometimes the best way to meet people is to just get lucky… and to understand what goes into making your own luck. Yes, meeting Mr., Ms. or Mx. Right is often a matter of luck. It’s the old saw of luck being the intersection of random chance and preparation, with a better understanding of what that preparation looks like and how to set it up so you don’t sandpaper your soul raw in the process.

The people who are the luckiest in general aren’t blessed by Loki or Tymora or they just happened to have caught Coyote on a good day. They’re the ones who put themselves in fortune’s path – living in such a way that makes serendipity more likely to happen. This way they’re in position to take full advantage when opportunities present themselves.

The easiest way to get lucky without going out and being on the dating market is simply to live your life, enjoy the activities you enjoy and otherwise have a good time in ways that bring you in contact with other, likeminded folks. You’re not looking for your perfect match, you’re just out doing the things you love and, in doing so, meeting people who also enjoy those things.

This may mean gardening clubs or amateur sports teams. It may mean taking conversational language classes or getting a pub quiz team together. Maybe it would involve political organizing or picking a charitable cause to champion. But by spending time doing the things you love and that feed your soul, with other folks who feel similarly, you increase the odds of meeting someone who would be right for you.

And the benefit of this approach is that it’s great for people like you, people who need time to warm up to folks and develop a connection first. Because you aren’t out there Dating – capital D – you don’t necessarily feel the same self-imposed pressure to speed through things. You can get to know people over time, build a connection to them and see how things grow. Someone may seem like they’d be a perfect match on paper, and you enjoy their company… but without that pressure to lock things down, you have the time to see whether the chemistry and compatibility is there or if they’re just someone who might make a good friend.

This is, after all, how most people tend to meet their partners. We very rarely start a relationship with a stranger shortly after meeting them; we tend to develop a connection over time. And since you’re not telling yourself that you need to be in a rush, you can take that time to see how things go. If it turns out they’re not right for you, then you aren’t out time that you might have spent elsewhere; they were part of what you were doing already. But if they are right for you, then you’ve had the most amazing bonus to living your life the way you like.

This is why we say that it’ll happen when you least expect it. Not making dating the forefront of your mind means that if and when it does happen, you’ll be pleasantly surprised.

If you take the pressure off yourself to get a particular result and simply live your life in ways that bring you in contact with people who share your interests in passions, you’ll have a much more enjoyable time. It won’t feel the way being On The Market does simply because… well, you’re not. You’re just out and about doing the things you love that just happen to make it more likely for serendipity to happen. And if it doesn’t happen – or in the way you expect – then you’re not out anything, because you still have the rewards of pursuing those passions and ambitions. It’s not quite win-win, but it’s certainly an outcome you’re already satisfied with.

So live your life in the way that brings you contentment and satisfaction, SSATY. Love knows where to find you when it’s 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: I’ve known this couple for about 3 years, and we’ve done a lot of things together through the years. Being their third wheel was never a problem, and I love them both. They were there with me during some of the hardest times of my life in work, dating, or other crises. They were my people, and I always looked forward to the weekends when I’d go to theirs for a movie night, play games, or paint with them. It was the best.

They broke up recently. I had tried to help them through their rough patches, as I’ve been divorced and raked over the coals in dating plenty of times. At the end of it all, they just weren’t compatible. At least not anymore.

Here’s where things got really complicated. These two have been in my life for so long at this point that I didn’t want to just pick a side and abandon the other. They both have requested to hang out individually with me and I’ve obliged. He told me he acknowledges that she and I will get close, and that he’s dating other women and that he’s moved on from the whole thing. Meanwhile, she’s admitted to feelings for me and we did end up sleeping together during a recent hang out.

I feel conflicted. I feel like a snake that played some long con that I never intended to play. She’s such a beautiful person, and we bonded through the years on our love for education, language, art, and our history of the same spiritual practices. It’s made the sex and intimacy otherworldly, and we just physically click in every way we’ve tried. Even our love languages intermingle well.

She’s emphasized that we’re two consenting adults doing adult things together, and that it’s our business, not anyone else’s. I can’t argue with that logic. She’s told me that she’s moved on, that they just weren’t compatible. She seems to understand why I feel conflicted, too.

I guess it’s just that whole question of where is the line drawn? Are we in the wrong for indulging ourselves with each other, and engaging in romance and intimacy together? Have I put myself into a horrible corner that will fracture my social circle? Or, as she’s put it, are we just two adults doing adult things, and that’s our business?

I never felt this way until she and I started spending more time alone together. It just felt different. I just feel like I won’t be able to look him in the eye anymore, and God forbid if he finds out.

I’m With Jesse’s Girl

DEAR I’M WITH JESSE’S GIRL: One of the things I’ve talked about before is how motivated reasoning can be a motherf--ker. The issue is that you start from a particular position or have an outcome that you want or expect and work backwards to justify it. It’s an issue that comes up in dating and relationships fairly frequently; you will see people start from the position that meeting someone is impossible or that women want X or Y and then come up with absurd examples or hypothetical scenarios that are so unlikely that you’d have better odds of winning the Powerball AND Mega Millions at the same time.

Well, that’s part of what you’re dealing with here, IWJG. This is one of those problems that’s only a problem because you’re expecting it to be one and everything is spinning out from there. You’ve created a scenario in your mind were somehow, unbeknownst to you, you’ve been plotting and planning for this exact moment.

Well, let me ask you something in all sincerity: which seems more reasonable to you? That somehow you are secretly Littlefinger, carefully nudging things and biding your time until circumstances lead to you finally getting what you want, or that you’ve been spending time with someone who shares a lot of your values and passions and has a similar background and a mutual attraction has developed organically?

While you mull that over, I’d point out that propinquity – the tendency to start relationships with people you spend the most time with – is one of the strongest and most underappreciated aspects of attraction. Considering that you’ve been hanging out with both of them for a long time and with her on an individual basis since the breakup, I wouldn’t say that this was inevitable, but one or both of you catching feelings to some degree is hardly a surprise. So I think you can give yourself a break on that count.

The next thing I would point out is that getting worked up about this and how your friend would feel is basically denying agency to his ex/your current snugglebunny. She’s hardly a naif or some babe in the woods to your big bad wolf. I have to agree with her on this: you’re both consenting single adults, doing the things that single consenting adults do. This really isn’t anyone’s business, and anyone who has a problem with it are welcome to keep that information to themselves. This includes any busybodies in your social circle who might feel like this is some grand betrayal. They’re welcome to think whatever they want, but their opinions only matter in as much as you allow them to. Relationships aren’t democracies; people can have opinions, but they don’t have a vote.

But even if you weren’t being a snake in the grass this entire time, what about bro code? What about your bro’s feelings? Aren’t you betraying him by being with her?

Well… what about them? I realize this is a stance that gets people annoyed at me, but… yeah, he may be your buddy, but this is no longer any of his business. They broke up. I’ve long said that you can’t call dibs on people and the corollary to that is that there’s also no rule of “I licked it and now it’s mine forever.” The fact that they used to date might – and I stress might – be temporarily awkward, but they are no longer a couple. There’s no more expectation of exclusivity and neither of them has the right to decide who the other can date or sleep with. Even if your bro has opinions about your seeing her, he doesn’t get a vote. The only people who get a say in who she sees going forward is her and the person she’s seeing. Which in this case, is you.

Just as importantly, he’s practically signed off on this hook up anyway. He told you in no uncertain terms that he expected this to happen and that he’s dating other people. He said, straight up, that he has moved on. He may not be standing on the flight deck, guiding you in for a landing but he certainly made it clear he’s not standing in the way either. If he discovers that no, he was only cool with it in the abstract… well, that’s a him problem, not a you problem, and it’s for him to deal with. And hopefully he’s got the emotional intelligence and maturity to recognize that rather than making it something for you to handle.

Will this fracture your social circle? I don’t know. People can get weird about the damndest things. I remember people I know who had an honest-to-god summit in order to hash out a couple’s break up and decide the best way to handle it, who got to stay and who got to go. The key, however, was that everyone involved wasn’t even of legal drinking age. I would assume that you all aren’t in high-school, and you’ve gotten over high-school drama, but for some folks, high-school never ends.

Should you conduct your affairs (as it were) as though that were the case? Absolutely the f--k not. I could see this being a concern if one or the other person were a monster during the relationship or the way they behaved during the breakup was especially heinous. But from what you’ve said, it was a fairly amicable and clean break: they were compatible until they weren’t and so they ended things. If other people think that it’s wrong, somehow, for a single woman to sleep with a single man simply because they were all in the same social circle, then I don’t know what to tell you except maybe you need friends with more emotional maturity than a high-school junior.

But honestly, nobody’s opinion, mine included, matters here. The only ones that do are yours and hers. You and she have found happiness together and that’s no small thing. Maybe this will be a fling like a comet – bright as it streaks across the sky but gone in the blink of an eye. Maybe this will be a love to last the ages. Either way, you don’t need to borrow trouble from the future. The fact is that right now you and she have something that brings you both joy and comfort; giving that up because of brain weasels and hypotheticals would be a low-down crying shame.

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 42 now. About a year ago, my relationship of five years ended. She broke up with me over sexual incompatibility issues, and likely other ones she never told me about, either before or after the breakup.

She had variously identified as ace or demisexual. I am very much not, but I absolutely respected her boundaries and never pushed for sexual contact. She occasionally (4-8 months) would ask me what I was missing from the relationship; while I always said it was just sex, I was always extremely clear that I was comfortable with her taking her time to figure herself out.

Six months before she broke up with me, she decided she would go to a specialist therapist to find herself out. I supported her throughout this, including financially. She decided that she did not want to have sex, ever, and broke up with me.

After she moved out, however, she told me that she had already decided she was going to break up with me two years prior. This information absolutely devastated me. Not immediately, but over the past year, I have recontextualized many incidents and I feel somewhat betrayed. Not only that, I had asked her about them at the time, and she assured me that all was fine and I had nothing to worry about. I no longer really trust my reading of other people now.

I don’t know what to do. I don’t want to be alone. Online dating is absolutely awful in my area. Women my age are either politically incompatible or have children in their teens to early adulthood, and I do not want to get into that kind of situation at all. Younger women (as in early 30s) don’t really seem to be interested in men my age, or also are politically incompatible. I’m most certainly not a conservative, and I absolutely cannot date a conservative either.

My friends are close to my age, and they’re almost all married or in stable relationships, and so are their friends. I’m not as able to get into hobby spaces, and the ones I’m more interested in (models and painting them) are very much more male dominated than not, and I straight up do not want to be “that guy” either, so I am avoiding talking to women at hobby spaces because I don’t want to risk putting anyone off of a hobby they enjoy.

I just don’t know. Maybe I’m being overly paranoid. Maybe I’m giving up too soon on online dating. But I feel terribly alone, and I just don’t have any tools to solve that issue.

All By Myself

DEAR ALL BY MYSELF: This is an awful experience and I’m so sorry you’re going through this, ABM. I know this feels like the world is ending and everything feels hopeless and pointless. But I promise you, it’s not nearly as bad as you think.

The first thing I think you need to keep in mind is that you are still neck deep in dealing with the shock of it all. One of the things that we don’t talk about when long-term relationships end is what it does to our sense of self. For several years, you weren’t just one person; you had adapted your life to incorporate another person into it. It’s easy to think that this just means sharing space with another person or having to factor them into your weekend plans, but in practice it means that you both restructured your life around having this partner with you. It goes beyond managing your social calendar or having someone to split the rent and chores; it means that every aspect of your life has been rearranged to accommodate the fact that there’re two of you now, not just one.

When you go to the grocery store, you’re taking your partners’ tastes and preferences and restrictions into consideration, not just yours. You factor their schedule into all the mundanities of life alongside yours. Gotta call the HVAC service to look at your furnace? You and your partner have to work out who can be around to let them in and show them where everything is. Gotta take the car in for an oil change? Well, maybe they can give you a lift. Want to go on vacation? The two of you are figuring out places you both want to go.

It’s really not hyperbole to suggest that this is very akin to someone losing a limb and having to adjust not just to the loss, but to the changes that you have to make because of it. You have these habits and routines and decisions that you’ve been making for so long that they’ve become muscle memory, things you do without thinking. But now suddenly she’s not there and her absence makes it clear just how much you lost. Not just her physical presence, but all the aspects of your life that she had become a part of. All those little things that you never really thought about, up until things changed and you realize just how much of a hole that she’s left.

Everything you did for half a decade was based around the expectation that your partner was part of the equation, in ways both large and obvious but also small, subtle and easily forgettable… right up until you get smacked in the space by their absence.

So right now, you’re having to relearn who you are without her and how to live as just one person again, instead of half of a couple. That’s hard. It takes time, and it’s going to be painful. As you relearn and readjust to your life, you’re going to find those negative spaces where she used to be in places you never thought of, and it will strike you like a hammer to your heart. But as time passes, you will find that those holes eventually close and before long you’ll realize with some surprise that you feel… almost normal. You will realize that the pain you’ve been carrying around has lessened without your perceiving it until suddenly you do. And it will feel weird, because it will happen both sooner than you expect and take longer than it feels like it should have. But it will happen.

But part of what you need to do during this transition period is to not worry about relationships or what comes next. You need to focus on the now and to process your feelings. And you’ve got a lot of feelings to process.

One of them is, honestly, a feeling of betrayal. It’s understandable and human to feel this way. You’ve been hit with the knowledge that she’s been feeling a particular way for longer than you thought and it’s forced you to reconsider everything. A breakup is almost always going to hurt, but this means that it is also going to feel like you’ve been lied to. And you have, in a way. She may not have realized it except in retrospect, and she may have done so in an attempt to spare you unnecessary hurt, but it still happened. So now you feel like you’ve been betrayed by someone you trusted. It may not be rational, it may not even be fair, but nobody said feelings were fair. They just are. We can argue whether it’s accurate or deserved, but the feelings are real.

But I think part of what you need to understand – as hard as this may be – is that this wasn’t about you and it wasn’t about you getting things wrong. She wasn’t being asexual at you. You didn’t turn her ace, nor did she do this maliciously. If anything, it sounds like she was trying to do the opposite and make it possible to stay. Those check-ins she did? Those tend to be the actions of someone who’s trying to make things work, to find a path that didn’t end with the two of you breaking up. I think that, at the end of the day, she genuinely cared for you and that ending this was the last thing that she wanted to do.   

But as the song says: sometimes love just ain’t enough. There was a fundamental incompatibility in your relationship, one that was at the core of who she was as a person, that could never be overcome. It wasn’t anybody’s fault; to say that it was would be like blaming someone for being left handed. It was just an obstacle that was ultimately insurmountable and at the end of the day, leaving was the least bad thing that could happen for the both of you.

Yeah, it hurts. It hurts a lot. And in retrospect, some of it is hurt that could’ve been avoided. It would’ve been better if she had ended things earlier, when she realized that she’d been thinking about leaving. But we make decisions based on the information we have at the time, and sometimes those decisions are the wrong ones. It seems likely to me that she stuck around those two extra years trying to change things, rather than doing so out of spite. With the perspective that comes with time and distance, I think she’d agree that her staying added an unnecessary level of pain to what was already a painful situation.

And to be perfectly frank, I think she was wrong to tell you that she’d decided to leave earlier than she did. I think this was needlessly cruel and absolutely unnecessary. While it doesn’t sound like she did so out of maliciousness, it was still information that you didn’t need to know, certainly not now. We talk about the importance of truth or honesty, but there’s a difference between truth and knowledge. It may be true that she decided to leave before she finally did… but that was knowledge you didn’t have or need. It didn’t clarify things or make things easier to understand; it just served to force you to reconsider everything in your relationship and cast a shadow over memories you had thought were happy or content. Sometimes we have a right to not know things, especially when knowing them does us no good and only causes more hurt.

But it is what it is and the only thing you can do now is move on. But you need to move on in ways that are actually good for you.

Part of the reason why you’re struggling right now is that, frankly, you’re still in mourning. You’re still processing everything, coming to terms with everything and you’re in a lot of pain. You’re still being haunted by those empty spaces and trying to make those feelings go away. But trying to fill them with bodies isn’t going to help – not the way you’re hoping it will. You’re looking for someone to not just to ease your loneliness but also to ease the sense of betrayal, the sense of confusion, that feeling of needing reaffirmation that you’re not just the guy people leave. You want to feel like you’re still capable of being loved. And you are. Her leaving didn’t change that, nor did it prove that you aren’t. But right now, diving into another relationship isn’t going to fix things. The wound is too raw, the hurt too deep. Any relationship you start now would be an attempt to fit someone into the spaces she left, and that’s a mistake.

Nobody could replace her, and nobody will. But that doesn’t mean that you’ll never date again. It just means you’re not ready, yet. You have to give yourself time so that you fill in the negative spaces she left behind yourself, so that you feel complete and whole again. You want to be in a place where you can welcome a new person into your life as that specific person, not as a replacement for your ex, like an understudy or recasting a role when the actor left. Otherwise, all you end up doing is prolonging the pain and the time it takes to recover.

Like an athlete who’s suffered an injury, you need time to recuperate and rehabilitate, so that you can get back in the game without making that injury worse.

But you will get there.

So here’s my advice for you. First, I want you to take care of yourself. Part of this is going to be to let yourself just feel. You don’t have to be reasonable about it, you don’t have to be fair; you’re allowed to be hurt and upset and angry without turning it in on yourself or blaming yourself because ultimately, there’s nothing to blame. Express that pain, that hurt, that betrayal. Let yourself be angry about it. Let the pain out. Yell into the night about how unfair it is. Lance that particular boil and let the infection drain away so that the healing can start.

Then the next thing I want is for you to take care of yourself. We talk a lot about self-care and it’s easy to think of self-care in terms of comfort or reassurance and some of it is. But the larger part of self-care is to literally care for yourself, to treat yourself as someone who deserves to be in good working order. In this case, taking care of yourself means making sure that you’re eating well – trying to make sure you’re getting healthy meals along with food that brings you comfort. It means getting exercise and making your body move. It means doing a deep clean of your house, like a spiritual cleansing of sorts to chase away the darkness of the past year.

And it means addressing your loneliness. Right now, a new relationship isn’t what you need; rather you want to look to your old relationships, your existing ones. You want to reach out to your friends and say “hey, I need you right now”. Let your friends offer you comfort and companionship, to help drown out the feeling of being alone. They may not be able to be with you 24/7 the way your ex was, but they will remind you that you’re not in this by yourself. No matter how much it may feel right now, you’re not as alone as you think.

And while you’re doing this, I think it would be good for you to find a purpose to devote yourself to. Feeling like you’re part of something bigger and contributing good to this world can be very important, especially in times like this. You clearly have a lot of love to give, so perhaps it’s time to give it a little more and to causes and communities that could use it.

This may be a good time to connect with your community and see what you can do to make it a little better, a little stronger and a little brighter. Maybe this is a time to take this love you have and share it with folks who could use it. Perhaps it’s time to foster a cat or a dog and give it a loving place to rest while it finds its forever home. Or it may be time to find a cause to volunteer for, whether it’s helping the unhoused and vulnerable, the people who’ve been cast off from society or the children and families who’ve been forced to flee from oppression. Knowing that your presence and your actions have made life better for others will go a long, long way to reminding you that you’re a good person, a loving person, a beloved person and that you matter.

That, I think, is going to be more important than trying to date. You’re not there yet, but you will get there.

It hurts, I know, but the pain will fade in time. It’s dark now, but there will be light again. It’s quiet, but there will be music and joy and laughter. There will be love again.

You’ll be ok. I promise.

All will be well.

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