Estimated reading time: 18 minutes
Hello Dr. NerdLove! Huge fan of your work, I practically have a playlist of your videos I often listen to in the background. But today, something had occurred to me, something that I feel I need to digest before making any major moves.
I’m 32(M) and have been out of a relationship for about a year and a half now. I’ve spent that time working on myself and trying to learn from the mistakes of my last relationship before I tried dating again. Recently, one of my newer friends had gone on a date with a woman, and I will admit it sparked a bit of jealousy in me. Not the malicious kind, but more the ‘I wish I could do that’ kind of jealousy. As a result, I have this strange urge to enter the dating pool again. But before I do, this question has been lingering on my mind all day:
“Am I wanting to get back into things because I genuinely feel ready, or is it because seeing my friend’s success has me feeling left out, and I’m suddenly wanting to jump in so I can say ‘I did it too!’? How can I tell I’m truly ready to start dating again versus just me being lonely and a bit jealous?”
I’ve been debating trying out some dating apps and perhaps looking further from my hometown in terms of social gatherings, but have yet to work up the courage to do so. But I know that I won’t succeed unless I’m ready to risk failure. There’s also the lingering notion that I may not have everything I need to be dateable: still currently live with my parents, but I contribute and help around the house and help alleviate stress off my parents. While I know not having your own place isn’t a dealbreaker for some, and in fact women are free to have those conditions if they please, but it has been a lingering insecurity for me.
TLDR: How do I know when I’m genuinely ready for dating again? How do you tell the difference between readiness and just loneliness? Should I try local, dating apps, or a mixture of the two? Hope you can understand my rambling! Thanks again for listening!
-Cloud Bird
I have a question for you in return, CB: what does “being ready” mean to you and why do you feel like this is something you need my sign-off for?
This isn’t a rhetorical question; I want you to think about why you’re hesitating instead of just deciding that you’d like to go on dates again. Understanding where your head is at is going to go a long way to helping determine what your next steps should be. But if you want my opinion? I think you’re creating a distinction for the sake of putting things off. And I think that’s a question worth investigating.
You don’t say why your last relationship ended, but you spent a year and a half apparently addressing things that came up during that relationship. Maybe you feel like there was some flaw you needed to address that affected your relationship. Maybe you, like many other people, got a little gunshy after the end of the relationship. If your break up was acrimonious, the cause of the break up was painful or you simply were dating someone who was wrong for you… yeah, I can understand why you might be worried. Similarly, if you feel like you did something wrong or you were missing some important quality or you needed to address an unhealed wound, it would make sense that you were worried about a repeat of past mistakes.
But it’s the way that you felt a pang of jealousy that your friend went on a date that leaps out at me. The phrasing suggests that it was the act of datingthat tweaked something in you, rather than the idea that your friend was out with a woman and you weren’t… less that you’re lonely but more that he is “allowed” to go on a date and you aren’t. That makes me wonder what you feel is holding you back… and frankly it’s what makes me wonder if you’re building “dating” into something bigger in your mind than just going out on a date with someone.
After all, it’s entirely possible to go on a date without it being anything more than just being A Date. Getting back into the dating scene – whether it’s talking to women in person or hanging your shingle out on the apps – really doesn’t commit you to anything, including just dates. There’s nothing stopping you from deciding to just date casually – meet people who seem interesting, go out and have a good time with them and not worry about it being anything more than “we go do stuff together and enjoy ourselves”. You’re not going to be locking yourself into a soul-pledge to enter into a long-term relationship by the end of the year or commit to a person as soon as you hit date three or whatever.
If it really is just a case of FOMO… why are you missing out? You mention things like “living with your parents”, but that’s really not a big deal. Leaving aside that 59% of Gen Z live in multi-generational homes, you’re living with your parents is hardly a sign that you’ve somehow failed to launch. You’re not a freeloader – you’re helping take care of your parents – but also let’s be real: rents and home prices are insane, salaries haven’t been keeping up with cost of living increases or inflation and that’s if you aren’t being living with someone in the C-suite deciding to axe your entire department because they’ve got AI psychosis.
So I wonder if the “being ready” here is less about being ready and more feeling like you’re worried that women are going to reject you. Which… well, yes. You’ll get rejected. That’s just dating. Everyone gets rejected. That has as much to do with meeting the right people as much as it has with being someone women want to date. There’s no way to ensure that you won’t get rejected and there’s no way to avoid all risk. You just have to accept that it can happen and learn to not overly invest in any one person until it’s time to invest in them… which is not before you’ve even had your first date.
And if that’s the case… you’re hardly alone. Most of the time, people who feel like they’re not ready to date “yet” are trying to avoid not just rejection but the fear of rejection – the discomfort of feeling afraid. But that doesn’t actually work; the more you avoid the things you’re afraid of, the worse your fear becomes and the larger it becomes to incorporate anything that reminds you of what you’re afraid of. The only way you can really conquer that fear is to face it head on. The only way out is through, so you may as well dive in and start swimming.
But like I said: all this means is that you’re putting yourself out there and opening yourself to the possibility of meeting people. That’s it. You don’t need to dive head first into commitment and swear to marry the first woman who says yes to getting coffee or dinner with you, nor do you need to be making it a goal to go on six dates a month with at least three people. This isn’t an all-or-nothing situation if you don’t want it to be; frankly, it’s a hell of a lot healthier if you don’t treat it that way. If you decide to just go out when you feel like it and see what happens and then spend other weekends hanging out with friends or having a chill night at home, that’s entirely fine too.
So, are you ready to date, or are you envious of your friend? Why does there need to be a distinction? Why can’t it be both? Or rather: why does it matter? If you decide to give it a shot and then realize that you’re not feeling it and need more time to work on whatever it is that you’re working on, that’s fine too. You’re not locked into whatever decision you make; you can take backsies and breaks, and then you can decide you’re done with the break too.
Personally, I think if you’re looking forward to going on dates again, then that’s all the reason you need to give it a try again.
It’s your call, CB; you are only as locked into this decision to the degree that you decide you are.
Good luck.
So, I’ve messaged before. You may remember. I worked on what you said.
Did pretty well on all that. To the point I look back and can’t even figure out how I thought all that crap.
I uh… still don’t really know what to do, though. See, you focused on my anger so much (which was helpful) that I don’t really know what to do now.
Like… after I got my shit together, I’ve spent about 6 months trying again, and there’s still the same problems.
So, to break down my experience more clearly with less anger:
I go to parties expressly for my interests (anime and nerd stuff. The afterparties for anime conventions specifically)
I look for people to talk to, guys and girls, because I know that if I just talk to the girls, it’ll be obvious. Plus, I’m trying to make FRIENDS first, as the first step, so why not include guys, make more friends. Win win. Like, I do HAVE an “ulterior” motive, but as a BONUS objective? when I set out, the only GOAL for that night/party is just to meet new people and make friends.
I approach (single guy, single girl, group of any) when they seem to be at a safe lull in conversation or otherwise approachable, introduce myself, and try to start a conversation about some indication of shared interest (a costume, a song, a piece of merch, etc.) [failure point 1. there doesn’t seem to be anything off about IMMEDIATE contact, like people aren’t looking at me disgusted or anything, but I still usually get cut off here]
I eventually mention that I don’t know many people here and I’d like to hang out, maybe get to be friends [fail point 2. plenty of people get outright weirded out here and I don’t know why]
If we somehow get past this point, which has happened maybe 4 times total after dozens of conversations per party, they quickly drop contact after the event.
I don’t know if it’s my, like, style? If it is where would I even find customized style advice? Like, it has to work what I’ve GOT right? Can’t just go for “This is stylish jacket” or whatever.
I don’t THINK its hygiene. Teeth, deodorant, clean and neat hair (as best I can… it’s starting to get thinner…), all the works accounted for.
Given the situation and costumes, I think I do pretty good on the wandering eyes issue? Like I don’t stare, and I do my absolute best on self-control and IDK how you’d measure this (eye-flicks-per-minute? XD) but I think I do pretty good. I certainly haven’t ever been directly accused/called out. I guess part of the issue is this one is hard to tell how good I’m doing on in the first place.
I’ve read a lot of advice in various places that says to not even be trying to get a GF and… I don’t know how to DO that mentally. I want one, so I’m working to get one. I don’t know how to stop wanting one. I don’t want to stop wanting one? Like… that defeats the purpose? Why is the only way to get something I want to stop wanting it? That feels unfair and confusing…
FWIW I do not NEED a GF. Life is GOOD. I’m pretty happy, and a GF isn’t a magic solution, I get that. But like… I’m still allowed to want one, right? The companionship, the support, the affection, and yes the sex. Which brings me to like, apparently horny is super bad? I’m not saying anything sexual to these ladies (at most “Nice costume”, which I feel is safe enough), but somehow it seems I’m giving off bad vibes. I WAS told once that its “clear I’m only here for the ladies”, which I don’t get how, I was talking with dudes too. THAT one feels really weird. Especially cause I’m maintaining eye contact or otherwise directing my eyes socially appropriately at like 90% of the time, worst case estimate (I feel like it’s closer to 99% but I might be wrong)
I also see a lot of advice about waiting for eye contact or a signal of some kind. That seems to NEVER happen for me, I’ve always had to initiate conversation. So I do really worry something is visually off about me somehow and I don’t know any way to check that.
What Am I Missing
There’s a lot going on here that I think you’re missing or misunderstanding, and that’s contributing to why you’re still struggling. I’m going to say this with as much empathy and compassion as I can, WAIM: if you’re coming off half as intense in person as you are in this letter, then I think that’s your number one problem.
This is, in fact, why I focused so much on your anger, rather than your social skills the last time you wrote in. There’s a level to which your intense focus and emotional investment in trying to date will backfire, and no amount of instruction is going to help until you recognize it, understand it and take steps to mitigate it.
Your current situation is a prime example of how it gets in the way. As I’ve said many times before: unless I’m following you around like I’m doing a documentary about the mating ritual of the Anime Nerd, I can’t tell you exactly where things are going wrong. But based on the vibe I’m getting from your letter, what seems likely to me is that you’re trying so hard to give off the impression that you’re not looking to get laid that you circle back around to trying too hard to get laid. Yes, I realize that seems inherently contradictory and confusing, but stick with me here, this will make sense in a moment.
There’re a couple issues here, starting with your misunderstanding what “don’t look for a girlfriend” means in this context. You’re seeing this as “don’t have an obvious agenda” and “visibly horny is bad”, which is part of what’s fucking you up. It sounds like it’s pretty clear that while you are open to making friends, you’re open to it because you see that as somehow being the key to getting a girl. That’s going to set off people’s Spidey-sense, especially if you’re protesting that you’re not.
Here’s an example of to keep in mind: have you ever seen someone in a tv show or movie who is very clearly trying to do something while not looking like they’re doing it? Maybe it’s someone who’s trying to angle for an invite to a party or ask someone out on a date or score some drugs or what-have-you. Michael Gandolfini’s portrayal of Daniel Blake in Daredevil: Born Again is a great example of this – whether he’s trying to get BB to go out with him or to arrange for better coverage for Wilson Fisk, he has an obvious agenda that he’s failing to hide. He’s clearly trying to work an angle, while trying to pretend that he doesn’t, and that sets people off.
It’s that specific sort of behavior, that sense of “we know what you’re trying to do, you’re not being subtle at all about it, so why are you trying to hide it” that people pick up on quickly. People don’t appreciate it when folks seem to be trying to trick them, which is why they get squirrely when they sense it. That’s almost certainly the vibe you’re giving people with the way you’re going about trying to meet people.
Now here’s the thing: when folks talk about “don’t go trying to get a girlfriend”, they mean one of two things, depending on the context. In the context of, say, going to afterparties at cons or going to salsa classes or hot yoga, what they mean is “don’t treat this like it’s a sex ATM”; dudes who are there to just pick up women disrupt the purpose of the event, whether it’s to dance, stretch and center yourself, or just hang out and have a good time with fellow weebs and otaku. It makes people uncomfortable and people will stop going if they feel uncomfortable.
In the context of “don’t try to get a girlfriend”, what they mean is that making this a goal of such dire importance is going to ultimately start fucking with how you’re behaving around other people and making people feel uncomfortable, while also setting you up for falling into a Hole-Marked-Girlfriend situation. In this case, what they’re suggesting is that you just do things that you enjoy, be social and meet people without any sort of agenda. Occasionally you’ll meet someone you’re attracted to, there’ll be a vibe, and then you can ask them out on a date.
You seem like you’re having a hard time with both contexts. You’re trying to hide what you’re doing and you’re so focused on the goal that it’s making you act weird. So what you need to do is just chill the fuck out and stop trying. Yes, I realize that’s hard to do when you’re horny and trying to meet people. But think of it like trying to grab wet soap; the harder you grasp it, the more it slips out of your fingers.
Here’s something I’ve learned over the years: things work a lot better when your goal is “there’s going to be a story tonight; I want to find out what that story is”. That is, be open to literally any possibility, whether that may be talking to a cool old dude who turns out to have lived a life of adventure in South America, making small talk with some folks at a bar, having a good time and ending up joining them at a speakeasy in LA’s Koreatown, or just going to a party and having a fun time. The last time I went to a party at an anime con with just a goal of “hey, interesting people will probably be there, I would like to meet interesting people…” I ended up getting drunk with Yamcha’s voice actor. Hooking up, getting dates, or even getting autographs weren’t on my agenda; talking with people and seeing where the night took me was.
That’s what you need to be striving for. It’ll make it a lot easier to just hang out, meet people and generally just have a good time, which will help you behave more like a person and less like a socially awkward Terminator scanning the room for Sarah Connor. Letting go of the agenda – not “seeming to” or “hiding it” but genuinely making your only agenda of “have a good time” – will make things go a lot more smoothly.
Now on a technical and mechanical level, there’re a few things you can be doing differently. For one thing: yes, there are people whose entire job is to help you dress better. They’re called “stylists” and this is a literal industry. A lot of department stores, especially ones like Nordstrom, will have personal shoppers and stylist services, but even the folks on the floor who ask if you need help finding anything can help you pick out some stuff that would look good on you. You just have to ask for assistance. There’re also folks who do style advice and fashion advice online and who teach about how to learn what does or doesn’t work and why. I’d suggest starting with reading Derek Kim’s blog Die, Workwear and following him (@dieworkwear) on Bluesky.
The second is that the way you describe yourself behaving is coming of as stilted and awkward, which is the opposite of what you want. The way you’re saying “I’d like to hang out and maybe become friends” is part of what’s throwing people. That’s generally not how people interact, especially with strangers; while it may be an honest goal, part of why it’s weird is that you barely know these people. Saying you’d like to be friends feels presumptuous since you don’t know them and you’re already giving of the “well, I’m really here to try to get a girlfriend” vibe.
In addition to getting used to letting go of an agenda other than just being social and having fun, part of what will help is adjusting how you’re interacting with them so you’re not falling into “the vibes are bad”.
What would work better is to focus a little more on getting to know them – who are they, how they know the other people in the group, what’ve they been doing at the con, what’s been cool, what’s sucked, etc. You can even say “yeah, I don’t really know anyone here, so I’m just trying to meet cool people,” and then turn the conversation back to getting to know them. This feels more organic and natural and doesn’t have the feeling of “why are you trying so hard?”
The last thing I will suggest is that you need to start getting better at being able to interact with people you find attractive without letting your horniness get in the way. While I don’t necessarily recommend this for everyone, and it may not necessarily be the best path forward for you, one of the ways that worked for me was hanging out in strip clubs and getting to know the dancers. Not, mind you, getting dances, but getting to know the dancers. It started with my realizing that spending an evening with my sketchbook at the club tended to be cheaper and more educational than most of the life-drawing classes that were available at the time (most of the dancers were willing to hold a pose or sit for a few minutes for $5-10 a pop and many would volunteer if I would give them the sketch afterwards), but later I would go and just focus on talking to the dancers and see how long I could keep them engaged in a genuine conversation before they either asked for a dance or had to go get dances from someone else. Either way, I’d pay them for their time (usually the price of a dance or two, depending on how long we talked) since they were at work, and then suggest that since I wasn’t really in the mood for a dance, they should find the guys who were. This had the net result of both my being able to have a conversation with a half-naked woman without letting my boner take over the conversation and a surprising number of casual friends.
But more than anything else my guy: stop looking so hard, especially when you’re still dealing with the social inexperience. You’re going to have much better results when you can just hang out with people and vibe, instead of trying to hide the agenda you so clearly have. Start there and I think you’ll find that things become less awkward and you have more success meeting cool people… some of whom may be women and some of whom may also be single and interested.
Good luck.
