Doctor’s Note: Around 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.
Welcome to Ask Dr. NerdLove: Revisited for 2026…
Today’s letter was originally published on October 21, 2019
DEAR DR. NERDLOVE: 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
DEAR 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.
Please send your questions to Dr. NerdLove at his website (www.doctornerdlove.com/contact); or to his email, doc@doctornerdlove.com