Estimated reading time: 14 minutes
Doctor’s Note: At the start of a new year, I like to look back and re-answer some older questions as I would if I had received them today. Whenever possible, I answer them without having read my previous response, to see and how my advice has changed in the intervening years. So this week, I’ll be going back and re-answering questions that I covered ten years ago.
Welcome to Ask Dr. NerdLove: Revisited for 2026…
This letter was originally published on March 11, 2016
I have a… situation, which I would appreciate your advice on.
A little more than a month ago, I went on a trip with a good friend (Let’s call her Alice) who I had an interest in romantically. Asked her out on the trip, she said no, we moved on gracefully. So far, so good, and I’ve maintained a close contact with her as friends. (Speaking of, I vastly appreciated your book’s advice how to handle this situation, as I’m sure prior I would have made things awkward). However, as I’m sure you’ve guessed, there are… complications.
First: her (stated, at least) reasons for rejecting me: One, that I had just gotten out of a long-term relationship; two, that she was still hung up on her ex (her first and only serious relationship thus far); three, that she’s going to be moving for work soon. Just in general, she appeared to be careful to leave the door open for “not now, maybe later”, although obviously I’m aware this might be wishful thinking on my part.
Second: While on this trip, I got relatively close to a girl we met. Nothing intimate, just had a great time with her and clicked pretty well. What was interesting is that Alice got noticeably jealous whenever I spent time with this girl, and spent a fair amount of energy trying to “warn me off” of her and/or convince me that she was just toying with me. In general, Alice acted relatively possessive/protective of me over the course of the trip, more than I would expect from a typical friend.
Third: While on this trip, Alice and I had several intimate discussions of the sort I’m not generally acquainted with having outside of relationships (sex, porn, eventual desire for children, detailed discussions of close friends’ relationships and their pitfalls, etc). Her best friend (also my very good friend, who was aware of and encouraged my interest) was surprised when I later told her what we’d talked about; these conversations were apparently well outside Alice’s norm.
All of this is background to the following: Prior to the end of the trip, Alice strongly suggested I take an extended break from dating to work on myself. The period suggested on the break was, conveniently, about long enough for all her time-sensitive personal issues to work themselves out… and more than long enough to eliminate any residual rebound angst. I agreed to it, but now I’m second-guessing myself. I’m not sure I like the idea of submitting myself to a “vetting period”, which I kinda feel like this is. Taking myself out of circulation for another chunk of time feels counter-productive, especially when one of the things I need to work on is how easily I get attached. And I’m worried about developing oneitis even more than I fear I already have.
So, all this being said: Is taking a break a good idea? Am I completely bonkers for interpreting her actions the way I have? And, if I’m right… is this really a sound foundation to build a relationship on, when I’m basically being asked to “prove myself” for this extended time period?
Off The Market
I’m going to be honest with you OTM, there’s a lot about Alice’s behavior that sets off my Spidey-sense. She doesn’t want to date you and has a long list of reasons why, but then she apparently got possessive and “protective” when you were flirting with another woman and then, suggested that you “take yourself off the market” for an indeterminate amount of time because you “need to work on yourself”. And while that time off would just “happen” to coincide with at least some of the period of time that she would presumably be unable to date, she also never gave a definitive “we’ll reconsider the question later”.
I’ll be blunt here: this sounds like someone who’s being really overt about keeping you on the hook. Under normal circumstances, I dislike giving credence to concepts like “plate-spinning” or “breadcrumbing”, because people love to use those terms to villainize women for acting like friends. But in this case… frankly, the way she’s acting actually fits the description.
Normally when someone’s trying to backburner you (or whatever cutsey term folks want to use), they’re giving you juuuust enough attention and time to keep you engaged, but otherwise are unavailable. They’re often inconsistent in how available they are – such as regularly making plans but canceling at the last minute, seeming to be “too busy” to see you but always have time for other people or never make definitive plans. You may, for example, find that they talk about getting together “soon” or say give non-committal answers if you ask to spend time with them. They often blow hot and cold; they’re distant and stand-offish when you want to see them, but seem to dial up the charm and attention if you start drifting away. Many times, you only seem to be a priority of theirs when they don’t have other plans. They rely on your availability while rarely returning the favor.
Other signs are lopsided or uneven levels of emotional intimacy or vulnerability, such as if they’re very attentive about sussing out your feelings, plans, desires and ambitions, but are more closed off when it comes to their side of the discussion and keep things to a very surface level. They keep you at arm’s length; you’re rarely a part of their “inner circle” as it were, even if you include them in yours. If you try to seek any sort of clarity or understanding of the nature of your relationship, they brush you off or otherwise give you very vague and non-committal answers. They may remind you of the casual nature of your relationship, even when the time you spend together seems like it should be more intimate and significant.
The fact that you’re feeling unsure and confused about what Alice is doing is a tell; you’re responding to vague promises and hopes, but no real certainty. At a time when you’re worried about oneitis and over-investing in someone – especially someone who hasn’t earned your emotional investment – she’s asking you to stay single because you “need it”. This seems to be counter-productive for your overall goals and needs, and yet the reason you’re considering it is the hope that maybe this will end with her being available and interested in dating you at some nebulous future time.
Now, the thing that bugs me is that she’s not entirely wrong in suggesting that you may want to focus on yourself rather than on dating. People who are prone to oneitis are usually coming from a place of lower self-esteem and scarcity; they’re often worried that their One is the only person who could be right for them, their last and only chance for true happiness. Taking time to work on themselves, build their confidence and sense of value and moving towards an abundance mindset are all great ways of breaking the emotional habits that lead to oneitis.
But this also just happens to coincide with your being interested in someone else… someone who was also apparently quite interested in you as well. This is quite the coincidence. In the words of a simple tailor: I’m a great believer in coincidences; they happen all the time. I just don’t trust them.
All of this sounds like she’s playing a game of “Go Away A Little Closer” to me. All her behavior sounds like someone who wants to keep your time and attention focused on her without any need to reciprocate unless and until she feels like it. It’s the way she tried to wave you away from the other woman and the “you shouldn’t be dating for a while” that really cinches it, in my opinion. It sounds to me like her goal is to make sure that you stay available; she wants you around, but on her terms. Her request is the sort that sounds reasonable, but is ultimately more about benefitting her, rather than you.
Now, maybe I’m overly cynical. Maybe she’s interested in you, but also knows she’s not in a good place to date. But if that’s the case, then she should say so. If she is hopeful that she’ll be in a place where she is ready to date you in the future… well, it’s good to want things, but she – like everyone else – has to accept the distinct possibility that you may have moved on or met someone else by then. It sucks, but that’s life. Trying to set things up to keep you available until then is shitty, even if the intentions behind it aren’t as underhanded as they seem.
Regardless: you’re single and ready to mingle. She isn’t, and won’t be for a while. If you were deciding to prioritize your emotional growth and well-being for your own sake, I’d say taking a break from dating is a fine idea. But doing it on someone else’s suggestion and in hopes that there’s a payoff for you at the end that goes beyond “being in better emotional shape”? That’s a bad idea all around.
If you’re going to choose to stay single for a while, do it on your own terms and in your own time. But under the current circumstances and with her involvement? Nah, my guy. If you’re gonna roll the dice, roll them on what may come your way, not on this “trial period”.
Good luck.
This letter was originally published on September 30, 2016
Before I start, I just wanted to say it gives me hope to know that you started out not being that great with women, and here you are now dispensing probably some of the best dating advice I have seen in my life, so it gives me hope.
I will give a brief description of myself: I am pretty young at 18 years old still in high-school during my senior year. I think I look pretty good in the face, but I am very skinny for a guy of my height of 6’4. To give a image, if I was any skinner I would probably look like one of those starved POWs in those war crime pictures in history books. I am not anorexic, but I am afraid that whenever I get intimate with a girl she will go “ew”. I haven’t had a problem with that with any of my exes, but I don’t know what they really thought in their minds…
Anyway, enough about me and to the meat of my problem. Senior ball is in February of next year near Valentines Day. I missed my junior prom due to my most recent ex breaking up with me a few weeks before it. This girl I am talking to right now is a really sweet person, but I don’t know how to connect with her. Well, I have known her for a year, she has flirted with me before but I never really got around to asking her out since I usually dated someone, or she dated someone. We aren’t close friends in the same social circle.
Well I decided to ask her out early in the year to senior ball, so I wouldn’t have to stress over it when the time approaches, and because I want to date her. Well she did agree to go with me. Everything seems fine right? Well no, because just because she agreed to do that doesn’t me we are dating yet. I am planning on asking her out pretty soon, but there is a problem… How do I know she likes me enough to date me?
I am a pretty shy person doc, and you have probably heard this before, but it seems like there are FEW girls in my area that share my interest and that are decent looking. How many girls do you know that live in rural south that collect Warhammer 40,000 miniatures, while reading every 40k book that comes out? Not many, and while I don’t need a GF that likes 40k, I just can’t really relate to many of them besides personality.
So in the recent days I have been texting her, and one time we were in a middle of a conversation about animals since she is a avid animal lover, and she just stops texting back. Granted it was late at night so she could have just fallen asleep, but its been a day since then and she hasn’t replied back even though she has been online recently. I just feel like she’s not attracted to me enough for a real relationship, and I really don’t want to go to the ball or prom alone this year, so I don’t want to push too hard too early and ruin that chance. When we talk in person it just seems awkward, probably because I am slightly nervous. There aren’t many people I am interested in, and the few that I am are either taken, or I have no idea how to approach them.
I can’t make a move, I can’t think of what to do next, and I sure as hell can’t flirt. I don’t know what to do Doc.
Sincerely,
No Game No Life
Let me give you the advice you need the most right now, NGNL: it’s time to stop thinking so much. Seriously.
Here’s the thing: all the overthinking you’re doing is understandable. It’s a form of self-protection; you’re trying to avoid getting hurt and avoid making other people uncomfortable, and so you’re trying to make sure you’ve got all the angles covered. That’s all completely reasonable.
The problem is that these sorts of self-protection can grow out of proportion to the actual need. They metastasize and spread until they no longer actually serve your needs; instead they end up putting you into analysis paralysis because you’re looking not only at every possible angle, but examining details and data that are so granular and nitpicky that you can’t possibly control for all of them.
Case in point: the lovely young woman you’re taking to the prom. This is a win, my guy. If you go with her to the prom and have a nice time together and nothing else happens… it’s an unquestionable win. Which is why it’s such a shame that you seem to be about to overthink yourself into snatching defeat from the jaws of victory.
You’ve pointed out that she already was flirting with you; that’s a positive sign that yes, she likes you. Y’know, on top of agreeing to go to prom with you. What about when she stopped responding to your messages? You already have the most likely answer: she fell asleep. Things felt stilted and awkward the next day because you felt awkward, because you have been running through all the angles like you’re analyzing the Zapruder film. Why did she not text the next day? Probably because you didn’t say anything. It’s a new day; instead of expecting her to pick things up where they left off, just send a different text. It can be literally anything that you would text any of your friends over – a funny meme, whatever tiktok made you laugh that you think she’d like, anything. Now you’re chatting again, until it reaches another natural lull, as every conversation does.
None of this is nearly as complicated as you make it out to be, and none of it requires as much stress as you’re putting yourself through. The ruminating doesn’t help; it only makes you more anxious, and you attempt to relieve that anxiety by trying to think it through even further, when what you need to do is just… nothing. Just let it all go, relax and enjoy the moment.
It’s like Bruce Lee said: “It’s like a finger pointing away to the moon. Don’t concentrate on the finger or you will miss all that heavenly glory.” Right now, you’re focused on so many things and so many questions, that you’re at risk of missing out on just having a good time at prom. You’re worried about things that come after prom. No, going with you to prom doesn’t mean that you’re dating; she agreed to go with you on a date. Focus on the date and just enjoying that. Will she want to date you? Possibly… but the time to ask is after you have a good time at the prom.
Showing her a good time may not guarantee a “yes”, but getting lost in your head about it – or, worse, making it a bone of contention before prom – runs the risk of her deciding not to go to the prom with you at all. So for right now, take the win and just be ready to enjoy the prom.
Then, either at the end of the night or the next day, that is when you ask her if she wants to date. You’ll be coming off the high of prom, having a great time and, importantly, you’ll be a hell of a lot more relaxed and at ease, so things won’t feel so stiff and stilted.
Will she say yes? Who knows? She may well still say “I’m flattered, but no.” But even if she does, you will have had a great time at prom, instead of wasting time worrying and anxious or, y’know, having not gotten to go to prom at all.
Take a deep breath, slow your roll and take the wins, my guy. It’ll all work out. I promise.
Good luck.
