Ask Dr. Nerdlove by Harris O'Malley

Is It A Good Time To Get Back With My Ex?

DEAR DR. NERDLOVE: First off, I’m really glad you do what you do. I’ve read through some of your material and it’s helped me so far.

Now, in order for my question to make sense I have to give some context. I’ll try and shorten this down as much as I can.

Met a girl through OKCupid sometime in 2016. Hit it off right away. She blew my mind and I was head over heels for her.

She was on again/off again with her (now) ex, and I met her during an “off” time. Well, I went to my first year of college out of state, and then transferred to a school in-state. So I was talking to here more once I was back. She was now dating her ex again.

From the beginning I could easily tell she liked me. That kind of attention and chemistry – I knew there was something there and it wasn’t just me. But she was still dating this guy.

Well, I was awash with infatuation and I wasn’t ready to walk away, so I stuck around. She was everything I’d ever wanted. Smart, passionate, a gamer and artist, had drive and goals, had a good head on her shoulders, good person, and drop dead gorgeous. Full package deal. Amazing.

From my perspective though, across the next 4 years, I felt… I felt like I wasn’t being treated well. It didn’t help that she was into me and was still dating her ex, and was torn, and dealing with her own emotions and life, etc – and I also let it continue. I couldn’t walk away yet. Wanting her was far greater of a force than sticking up for my worth. We would only hang out sporadically, and rarely. It was always last minute and was late at night or something similar where I was compartmentalized from the rest of her life. We never *really* went out and did stuff. It was 99% of the time at her house, sitting and talking or watching a show. Not that I don’t want that, but not at the expense of doing anything else.

Well, I walked away the first time in 2018, and she roped me back in. Then again about 6 months later. Then about another 3-6 months after that.

The last time she pulled me back into her life was at the end of August, last year. We met and talked for 3 hours, she confessed to having been REALLY into me this whole time (she had even had dreams about me during the time I had walked away.) and just… didn’t know how to handle that, didn’t feel comfortable with it yet, etc.

She said she only came back because she felt like she was over her ex and wanted to treat me right instead of as a recovery. She even kissed me.

Well, she’d been planning and working up to transferring/going to school across the country, and it was going to happen starting in January.

So I wanted to make the last 4 months she was here great: go on adventures, eat, have a blast, and have some fun in the bedroom. (Which she had opened up about wanting for awhile, but again wasn’t comfortable with it yet.) (we never did.)

So we hung out a few times, and then, of course, it felt like it went back to how it had been before: rarely seeing each other, at-arm’s-length, compartmentalized, etc.

I ended up not seeing her at all for about the last month of her being here, and I called her while she was at a hotel room in St. Louis while on her drive to school. Basically, I ended it. I told her that we hadn’t actually taken any steps forward and I needed to walk away. I think she knew the conversation was coming but was hoping it wouldn’t. When I told her this was it, she talked about how I was one of the only people in her life anymore that she felt close enough to and trusted enough to talk about things with, etc etc.

She then added that “I figured we would keep talking and stuff and we would pick up where we left off when I came back for the summer, just like I’ve done with… all… my… relationships….” (I used ellipses to try and show how, when she said this, she ended up slowly trailing off as the sentence went on, because I think she realized how shitty it sounded.)

I told her that it wasn’t fair to me to wait around and essentially twiddle my thumbs until she came back, with no guarantee of it actually being anything when she did. I shouldn’t have to put my life on hold anymore than I already had.

I told her that, if she reaches a point in her life where she wants me to be a part of it and I’m a legitimate priority, she should come and find me and we would see what happens. (A priority as opposed to what felt like just an option – because I was never really a priority – other friends, family, and other things were always more important or urgent than me.) it ended amicably, I told her I loved her and to “go be successful”.

I will say, up front, that I know I had issues of my own that were a problem. I had expectations, I had a lot of trust issues.

She has insecurities and self worth issues, and I was honestly looking to her to give my life meaning for a long time. Not the most recent stint, but for a long time before I was.

Sorry if that was a bit long winded, it’s a long story.

NOW – it’s been almost 3 months since she’s left, and we haven’t spoken since. I do still care about her, and there is a large part of me that misses her. That’s the same part of me that is considering contacting her and seeing how she’s doing. (In part to see if she’s ok, given the recent pandemic going on.) part of me misses her. Still wants her. Still wants to do all the things we said we’d do. I don’t want to have her as a regret in my life because we didn’t actually move forward. And I still want her.

However – do I trust her again and believe that things will be different? Is it a waste of my time and energy to invite her back in, given that she will be going back to school I’m the fall and, once graduated, be moving to that end of the country/somewhere else in pursuit of her career? Am I BS’ing myself in thinking that there really actually was a chance for anything to happen, or was she just not being truly honest with herself and didn’t have the same feelings? Was her indecision and at-arms-length treatment a much better indicator of her interest and intentions than her words?

And lastly, do I miss HER or am I really just struggling to feel like I have a chance finding someone else as amazing, or that I’m worth being with someone else as amazing?

I’ve struggled with feeling “good enough” for most of my life – one of my parents was always critical, even when given a compliment, and I think it created my struggles with self worth, or at least started them. I’m much better now, but I’m wondering if it’s really that I’m feeling like I have a better chance with her than anyone else because I’m “not worthy” of love.

I don’t know. I’ve been mulling over this for about a week, and I’m just filled with uncertainty. Is there a “litmus rest” or a question to ask myself in order to weed through some of these thoughts?

I hope you can help, I’m not sure what to do/how to approach this.

Also, probably way too wordy, so sorry for that.

Really appreciate the help,

Just When I Think I’m Out…

DEAR JUST WHEN I THINK I’M OUT: have you ever heard the phrase “the definition of insanity is doing the same thing and expecting a different result?” That’s where you’re at, right now. The idea that a) she’s going to come back and b) things will be different is… well, honestly it’s kind of laughable, if I’m perfectly honest. I mean, dude. You’ve been in this pattern for four! YEARS! You know exactly how this is going to play out if you go back.

Now look, I get it. God knows in my time I’ve had folks who played the “go away a little closer” game that kept me on the hook for a while. But sometimes it can help to examine just what was going on with her… and why you’re having such a hard time getting over her.

I’m going to be blunt: you were never really in the running for being her boyfriend. You were, at best, a distraction. You provided her emotional intimacy and validation but that’s it… and always on her terms and her schedule. I mean, let’s start with the fact that she was in a closed, monogamous relationship and she’s keeping you around and telling you how into you she is. While it’s true that sometimes it can be hard to end a dodgy relationship and some folks will start flirting (or even sleeping with) someone else in order to force the break-up, it’s pretty clear that you were the guy she turned to because you’d give her the emotional intimacy and validation she craved, without needing to give you anything from her end of things.

You even say it yourself:

“We would only hang out sporadically, and rarely. It was always last minute and was late at night or something similar where I was compartmentalized from the rest of her life. We never really went out and did stuff. It was 99% of the time at her house, sitting and talking or watching a show. Not that I don’t want that, but not at the expense of doing anything else.”

I’m sorry dude but you were her emotional side-piece. Her “in case of feels emergency, break glass” pseudo-boyfriend. That’s why you’d get those last-minute, can’t-go-anywhere-we-might-be-seen hang-out invitations. She didn’t want to take the risk of word getting out that she was hanging out with you, while also giving you just enough to keep you on the line. It’s pretty significant that for all that she tells you how she’s SO into you and has dreams about you and wants to “treat you right”, literally nothing ever happened. She never treated you like a boyfriend or a potential lover. She gave you just enough hope to think that this might be the time you two finally got together because it kept you around.

Shit dude, she literally said that she wanted you sticking around until she decided to come back again. Once you said “Yo, I’m out,” and meant it, she couldn’t even keep up the pretense that anything would happen. It’s not that she realized how shitty things sounded as she said them, it’s more that she realized that this line was going to work this time.

So no. Getting back in touch with her would be a profoundly stupid idea. All you’re going to get is the 12″ dance remix of the last four years, with her dangling just enough hope in front of you that you keep giving her what she wants and receive literally nothing in return.

That’s no way to live, man.

Like I said: I get it. She’s a lot like an earworm; you’ve had this little fantasy playing in your head all this time and you really want to make things happen so that you can finally close the loop and exorcise the song. But that’s not gonna happen. It’s never going to happen. You’re a kitten chasing after a laser pointer; even if you “catch” it, there’s nothing to catch.

But here’s the thing: the reason why it’s so hard for you to give her up is because you’ve spent so much time on her. I mean, four years is a long-ass time to be carrying a torch for someone. If you were to give up now, it’s going to feel like those four years were for nothing, and that’s really hard to accept. It’s what’s known as the sunk cost fallacy; you don’t want to admit that you lost all that time and effort and so you throw even MORE at it in hopes of making things work. But it won’t. The only healthy option you have here is to write this off as a loss, learn from it and move forward.

And before you ask: no, there is no way to try to keep this to just being a “just friends” thing. That’s the emotional equivalent of playing “just the tip”; all that’s going to happen is that you’re going to get roped back in again and then having this exact same conversation three to six months down the line.

So you need to excise her from your life. You need to treat this like a break-up. That means it’s time to take the Nuclear Option and cut off all the forms of contact you have with her. That means deleting her number and texts, blocking her on social media, archiving all of her emails and gathering up all the souvenirs of your relationship and stashing them away. You want to put as many steps between you and your getting back in contact with her; the more effort it takes to reach her, the easier it is to resist. Right now there just isn’t any way that you can contact her that won’t end in your getting sucked back in, so you need to make it as difficult as possible.

And while you’re doing that? You need to put yourself back out there. You’ve spent four years hoping for a relationship that was never going to happen. That’s four years that you could’ve spent finding someone who is just as awesome as her — if not more so — but who also wants you back. You may never get that time back, but that doesn’t mean you can’t start now and find somebody else.

Letting her go is the kindest thing you can do for yourself. You worry about feeling good enough. You worry about being worthy of love and affection. Here is a truth: there is no expression of self-love and self-worth greater than to tell yourself that you deserve more and better than anything she was offering you. It’s not whether you are good enough for the love of other people, it’s whether they are good enough for your love, time and attention. And your ex? She very clearly isn’t.

To quote the sage: “I may love you, yeah, but I love me more.”

Cut her off and cut her out, man. It’s hard to let go of a dream, but sometimes the point of a dream is to wake up from it.

It’s time to start the next chapter in your life.

You’ve got this.

All will be well.

Please send your questions to Dr. NerdLove at his website (; or to his email,