My Ex Won’t Date Me… So Why Won’t She Let Me Move On?

Estimated reading time: 16 minutes

Doctor’s Note: Hey NerdLovers! Last year was rough on a lot of people, and I want to help start 2025 off on a positive note. So I want to hear from you: what are some of your relationship wins? How have you improved your personal life, your friendships or your romantic relationships? What are some of the ways you’ve made your life better recently? Let’s share some hope, some positivity and success to help inspire folks to achieve their own victories.

Send your success stories to doc@doctornerdlove.com with the subject header “Relationship Wins”; maybe you’ll see your success story in a future column.

Hey Doc,

I’ve never been this confused in my life.

I’m 41, divorced (amicably-ish) with two kids, and, honestly, kind of lonely. Our co-parenting arrangement gives me enough time for myself now that the kids aren’t babies anymore. My eldest has a mental disability, which keeps me on my toes, but I’m managing to provide for my family just fine. Financially, I’m stable — I support my kids and even help my ex-wife. Basically, I’m just your average guy trying to survive in this crazy world.

Then, this average guy made a mess of things.

I fell for a much younger coworker (she’s 26). We’re still working together in a very close arrangement, which makes this even messier.

Here’s the gist: we work well together — so well that we started sleeping together. Then we stopped. Then we started seeing each other again. Then stopped again. Now, we’re in this limbo where we don’t quite know how to treat each other.

For my part, I’ve been clear: my feelings for her are real. I care about her deeply. She says she cares about me too but has insinuated that I’m not the guy she’d marry. That’s probably because of my status, my age, and the fact that I’m Muslim and she’s Christian.

I can handle “no.” What confuses me is the back-and-forth. When we’re together, she’s either distant or super clingy. One time, we broke up because I made a joke she didn’t like. A week later, she called saying she missed me, and we were back together.

Right now, we’re “off” again – this time because of something else I said. I told her I’d respect her decision, but it doesn’t make it hurt any less. So, I’ve been keeping my distance.

Here’s where it gets tricky: she doesn’t want me to distance myself. She wants to keep me as a close friend. But I want more. This has led to arguments because she keeps reaching out, and I keep rejecting her. That cycle finally upset her enough to declare we’d only talk as colleagues.

Except… that wasn’t true. Recently, she asked to meet up and admitted she didn’t mean it. She doesn’t want to lose me as her closest friend. I explained my feelings — again — and she seems to get it now.

The problem? It’s me. I still want to be close to her, but I know I shouldn’t. It’s been weeks since our last heart-to-heart, months since we last slept together, and I still can’t stop thinking about her. Working closely with her doesn’t help. She can be so needy, seeking me out when I’m trying to maintain boundaries. I can’t even bring myself to meet other women!

I’ve wondered if I’m white-knighting. She’s had a tough past: her father left her when she was very young, she grew up in a single-mother household, and she had a failed engagement just a year before our relationship.

Help me, Doc. Is this sociopathic behavior? Will time or space fix this? Or do I quit my 10+-year job over it?

Sincerely,

Who’s The Weird One Here?

Once again, I am asking people to actually learn what terms mean before they start tossing them around casually. Sociopathy has specific meanings – someone who is indifferent to right and wrong and no regard for the feelings of others, who disregard risk and safety (for themselves as well as people around them), uses lies, manipulation and trickery to get people to obey their whims and tends to casually disregard personal responsibilities or obligations while maintaining a belief in their personal superiority to everyone else.

Now I get why some of that may feel like it applies to your co-worker / ex. But here’s an important difference: true sociopaths tend to have a difficulty holding down jobs and are frequently in varying forms of legal trouble because rules just “don’t apply” to them. They also tend to be hostile and aggressive, often lashing out angrily at others and have few qualms about reacting violently.

None of that seems to apply to your co-worker. Most of what you seem to be describing is someone who doesn’t seem to know how to communicate what she wants and seems to be really immature for her age. That whole “go away closer” schtick? That’s the sort of thing I expect to see in high-schoolers and college students more than grown-ass adults. Calling her (or her behavior) sociopathic is hyperbolic at best when most of her behavior is just really consistently annoying. Understandably so and incredibly frustrating I’m sure… but not sociopathic, nor indicative of a mental condition. It sounds to me like she needs to grow the hell up more than anything else.

But that’s a side issue. Let’s focus on you and your relationship with her. If I’m being honest, I don’t think this relationship has a future, and part of the problem is that neither of you are really covering yourselves in glory here. To be sure: she’s holding onto the lion’s share of the blame, but you’ve got some issues of your own that need to get sorted.

The first thing to consider is that while you all clearly have physical chemistry together – you can’t seem to stop falling into bed, after all – you are not remotely compatible. The problem is that good sex can sometimes hide the fact that the only thing you have is that sexual chemistry. As the bard once said: “but what happens when you’re not in bed?”

Well as we’ve seen, we get something of a train wreck, because you two aren’t suited for each other. You want very different things, you’re in different stages in life and, as I noted, she seems incapable of communicating like a grown-ass adult. It would be one thing if you were only interested in an occasional fling or if she could admit what she actually wanted, but you aren’t and she apparently can’t. So here we are.

Part of the problem is that she doesn’t know what she wants, and I suspect part of this is because there’s a conflicting narrative going on in her head. On the one hand, she seems to want you in her life and gets anxious when you threaten to distance yourself. On the other, she seems to have an emotional narrative that keeps you at a distance – starting with “you’re not the person I’d marry”. Maybe it’s because you’re Muslim, maybe it’s because you’re older than her, hell, maybe it’s because she doesn’t like it when you switch hands when using a knife and fork at dinner. The reason is ultimately irrelevant because it’s just an excuse; the real issue, I suspect, is that this goes against some vision she has for what she thinks she’s supposed to want or do.

This is something a lot of people across the gender spectrum struggle with: what they think they want (or were told to want) conflicts with how they actually feel. Until they resolve that conflict and can take ownership of their decision, one way or the other, they create these absurd and frustrating loops that they can’t seem to break out of. But – dragging this back, kicking and screaming to your situation – that’s a them problem, not a you problem. It’s not on you to resolve this issue, nor is it really something you can do for them. This is a time where you have to be willing to stand up for yourself and realize that this relationship is simply untenable. You have to put your own oxygen mask on first before you can help others with theirs, and you’ve been failing to do so.

You say it yourself: she wants to keep you as her closest friend and you want more. Well… you’re not going to get it. She’s demonstrated this often enough. She sounds like she’s in a place where she probably shouldn’t be dating anyone, never mind someone who clearly wants a deeper level of commitment than she’s willing or able to offer or accept.

But your continuing to hold onto hope that maybe there’s a way to thread this needle isn’t helping either. Your relationship was so fragile that a poorly thought-out joke is going to end it, but said joke was not egregious enough to keep her from wanting you back a week later? Cool… then the joke wasn’t the problem. Something else was, and the joke was the excuse. But if she doesn’t know what the real issue was – or doesn’t want to tell you – then the relationship simply isn’t going to work because you’re going to inevitably hit that tripwire again and set that cycle off.

Another important issue is that she seems to have no respect for your boundaries. You’ve tried to put distance between the two of you for your own emotional self-protection. This is good and the right thing to do. However, every time you do, she throws a fit because she doesn’t want to lose you as a “friend”. Which, ok, sure, it’s good to want things. But being “just” friends with her and the level of intimacy she seems to need is hurting you.

But you’re not helping yourself here because when you get the inevitable pushback from your boundaries, you fold like cardboard. All that does is tell her that you don’t have boundaries, you have strongly worded suggestions. And to be quite frank, they don’t even seem to be that strongly worded.

It’s not exactly a puzzler as to why; you’re still holding out hope that you can pull out a win like a bad poker player hoping to draw an inside straight on the river. Well, look, I’ve been there and done that myself and I am here from the future to tell you: it ain’t going to happen. All that’s going to happen is that you’re going to end up in this cycle of “you get closer, she pulls back, you suggest a boundary, she gets clingy, you give in, she pulls back” again. You’re going to have another heart-to-heart, you’re going to think that maybe this time she gets it and the cycle will repeat all over again. Fifth verse, same as the first, a little bit louder and a little bit worse.

This is, as the saying goes, a curious game, because the only way to win is not to play. Well, you’re well past the point of needing to stop playing. The only way this cycle is going to end is that you need to stick to your guns. You aren’t going to have a relationship with her. Her “friendship” is exhausting because she’s needy and dumps all her neediness on you. Breaking this cycle is going to require that you finally let go of the idea of dating her, establish some firm boundaries and enforce them. This means not giving in to her little tantrums, nor to her begging and pleading. You have to be willing to say “I told you what sort of relationship I was willing to have with you; this isn’t it,” and to refuse to fold again.

Will this have consequences? Of course. It means she’s going to be pissed. It means that you’re going to have to accept not having her in your life in any form except as a co-worker. But that’s the thing about boundaries: they come with consequences. If there weren’t consequences, you wouldn’t need the boundary. The consequences are part of how people try to push past those boundaries. Accepting those consequences is an important part of having those boundaries in the first place: you’re reminding yourself that sometimes you have to put yourself and your own needs first, even when other people object. Strenuously.

And, again, to be blunt: this is why you can’t move on. You’re holding out hope that this is a situation that will change and it won’t. You can’t change it, no matter how many heart to hearts you have. It will change only if and when she is willing to change, and there is no guarantee that day will come, nor that it will change in your favor.

You had a fling with someone who ultimately wasn’t right for you, and it didn’t work. It’s a shame, but there will be others in the future. The best thing you can do is love yourself enough to let this go and move on.

Good luck.

Dear Dr. NerdLove

I know you’ve covered this topic before, and I apologize for bringing it up again. However, I have a question that I’m quite curious about. I am a man in my mid-20s who is still a virgin, and lacks dating experience. I’m not looking to ask whether a guy should tell his partner about his virginity or if women care about it (though I am somewhat curious about that). My question is this: for men who find themselves in this situation not by choice, what advice would you offer to steer them away from the pick-up artist approach?

I understand that pick-up artistry focuses heavily on practicality with little regard for genuine connection, and it often seems like a way to satisfy one’s own needs without truly bonding with a partner. How can these men be encouraged to move away from this mindset and toward a healthier way of losing their virginity, avoiding feelings of shame in the process? Thank you in advance for your response.

Unicorn Bait

Here’s the thing: the issue isn’t pick-up artistry per se. Pick-up and PUAs are a symptom, not a cause. The issue is the belief that being a virgin is inherently shameful and that a person’s worth is measured by the amount of sex they have or haven’t had.

If the issue truly was about whether someone has had a sexual experience or not, then it would be easily remedied. It’s a money-soluble problem – sex workers exist after all. There’re many who offer what’s known as a “girlfriend experience” – that is, providing an experience that feels more like an organic connection instead of a purely transactional exchange of money for services – and many who are perfectly happy to provide a virgin with their first experience. And honestly, for many people, that would likely be a better and more enjoyable first time than they might have had otherwise; they would be with someone who is sensitive to their needs and desires, whose focus will be on their pleasure and can help address or alleviate any of the little anxieties, mishaps or performance problems that might arise. They wouldn’t have to worry about their endurance, not being “good” their first time out or any of the other little bites from the anxiety weasels. Compare that to, say, a fumbling hook-up with a stranger you met at a bar or a date from a dating app and you can see how even the thrill of having had sex gets subsumed by the noise from their jerkbrains.

But that’s not the issue with losing one’s virginity. The issue is that what they want is to feel like they were chosen, that women have found them “worthy” enough to have sex with. This is why hiring a sex worker is seen as “cheating” or the mark of being a loser; they haven’t been chosen, they “have” to pay to get someone in bed.

Now personally speaking, I’m agnostic about how someone “should” lose their virginity. I don’t think you need to be “in love”, nor does it need to be with “someone special”. Losing your virginity doesn’t need to be a big production or special event. My only rule for how someone should have their first time is that the experience should be worth it. So, ideally, you would want your first time having sex to be with someone who is going to be a good and caring lover, who’s attentive and patient. That may be with a paid professional, it may be with a friend or acquaintance, it may be with a relative stranger. It could be a big production, or it could be the unexpected (but welcome) end to a date. It could even be a “Here, let’s get this over with/out of the way” if everyone’s cool with it.

But this approach is uncertain. Obviously, this requires the consent and participation of another person, and that is by no means assured. The appeal of PUA is that it promises men that if you follow these rules, you’re all but guaranteed success, that you will somehow convince a woman that you’re “worthy” and thus get in her pants. And therein lies the issue: it’s almost never about building a real and genuine connection; it’s about getting what you want in the way you want it. If we accept the idea that women only have sex with someone who’s “worthy” (we don’t, but we can pretend for the sake of this letter), then PUA is about how to fake being “worthy” or convince women that you are, even (or especially) if you’re not.

But as I keep saying, over and over again: women aren’t Mjolnir. People who decide to have sex with you aren’t gauging your worth as a person. Nobody has “anyone who parts these thighs, if they be worthy, shall have the power of SCORE” tattooed on their pubic mound.

(If only because that’s a lot of words to cram into a relatively constrained space.)

This is why the real problem ­– say it with me now – was toxic masculinity all along. As long as guys hold themselves to the idea that sex is a measure of their worth as a person and the corresponding belief that women are the “gatekeepers” of sex, there will be shame around the issue of virginity. There will be pressure to focus on the short term goal of “get laid as quickly as possible” rather than trying to find and connect with someone who would be a good lover, or, for that matter, developing the skills to connect with that person.

PUA is, at best, a short cut to that personal development. Obviously, I’m all in favor of teaching people how to date, how to flirt, how to meet and connect with folks and how to find the sort of sex you want – whether in a committed relationship or lots of casual connections or any point in between. But PUA is about skipping ahead to the end. The success people find tends to be despite what they’ve been taught, not because of it, and most of what they learn are tricks, not real personal growth and what success they find tends to be fleeting at best. Trust me, I speak from personal experience; I learned a lot from my days as a PUA, but I had to unlearn nearly as much and untangle the toxic bullshit from what was actually helpful.

This is why there’s not an easy or simple fix; it’s a societal issue. Without detangling sex and sexual experience from one’s sense of worth, the sense of shame and inadequacy will be there. Teaching boys that their value is distinct from who they’ve fucked is a key part. So too are treating social skills like skills, abilities that are taught and learned, rather than a binary that you either have or you don’t.

(And then we get into the incredibly sex-negative and queerphobic cultural issues, but that’s another rant entirely…)

In the short term, encouraging them to focus on both their sense of self-worth (independent of sexual experience) and their social skills and calibration is key. This way, when they do find someone to sleep with, the experience will be a good one for its own sake… not because of what it “means” about them.

Good luck.