Estimated reading time: 16 minutes
Dear Dr. NerdLove:
Over the last couple of years, I’ve decided that I’m tired of being single and devoted myself to getting to a place where I’d be someone women would want to date. Beyond doing things like trying to be a better communicator or more in touch with my emotions, I’ve been working on finding things I’m passionate about that also, I think, make me a good catch.
Among other things, I’ve learned how to dance, I’m a very good cook, I’ve taken comedy and speech classes to figure out how to be funnier and I’ve even gotten back into music, where I play multiple instruments. I may never be in a band, but I can strum a guitar like I know what I’m doing and I regularly impress people at karaoke. All in all, I’m really happy with my progress and in the process it’s helped me reconnect with things I loved as a child as well as find a new and great social circle. I made lots of friends since I started, which makes all of this worth it on its own.
The thing I struggle with now is that I don’t know how women are supposed to know I have these qualities. I don’t really see any way to bring up that I play guitar, piano and saxophone organically or that I know my way around a sauce pan. I suppose I could invite them on dates that would let me show off, but first I have to get them interested in me in the first place and I don’t think women are going to want me to come to their house or over to my apartment to cook for them when they barely know me. Do I just say “hey, here are all the cool things about me” and hope they want me to prove it? Do I just show all the pictures I took when I went to a two week cooking course in Paris or video of me on my dance class’ website? What do I do to show women I’m the kind of guy they say they want?
Under Cover Romeo
Congratulations on the work you’ve been doing and all the good things it’s brought to your life, UCR. It sounds like you’ve been putting in a lot of effort, which is great, and it’s helping you become a person you’ve always wanted to be, which is even better. So you should be proud of yourself and what you’ve accomplished so far.
Now to get to your issue: you’re right, having these qualities don’t necessarily help if folks don’t know that you have them. But informing people that you have them in a way that people can believe or that doesn’t make you look like a douchebag can be a challenge. Sure, you could just say it – and that’s something of an option on dating apps where you can mention things in your profile. But anyone can say shit… getting people to believe it, respect it or be interested it can be a tricky beast.
The primary option is going to be to focus on “show, don’t tell”. That is, if you want people to know about these qualities you have, then the best way to inform them is to demonstrate those qualities in some way, shape or form. For example, you don’t want to tell people you’re funny, you want to be funny. Being able to make someone laugh when you’re talking to them, for example, shows that you’re funny.
Now as you said: some of these qualities, interests and hobbies are harder to demonstrate on the fly. It’s hard to organically arrange opportunities to sing for someone or find a moment to spontaneously ask someone to dance if you’re, say, chatting up someone you met in the History section at a book store. But that’s not the same as impossible; it just means that you want to keep an eye out for opportunities to talk about such things. If, for example, you’re at that bookstore and near the cooking section, talking about favorite dishes or cuisine (Thai vs. French vs. interior Mexican) can give you an opening to talk about meals you’ve made or challenges you’ve had learning how to make certain dishes.
Another way you can subtly introduce that you do cool things and have cool hobbies is to tell stories. Being able to tell stories offer you a number of ways to signal these cool things about yourself. For one thing, being able to tell an interesting story is a skill in itself; the fact that you can hold their attention and tell a story that elicits a laugh, an “aww” or a “wow that’s really cool” is going to make you more appealing in general. Being fun is incredibly attractive; we instinctively prioritize spending time with people whose company we enjoy after all. If someone has interesting stories and can tell them in an engaging and fun way, that’s going to give you a bonus to those charisma checks.
But the other benefit of telling stories is that it allows you to allude to these other, attractive aspects of yourself in ways that feel organic and unforced but without coming across like you’re bragging. The key is that you want to tell stories in ways that communicate these qualities without necessarily saying that you have them. Talking about the wild experience you had in Paris while you were at that cooking class, for example, sub-communicates that you’re adventurous and well-traveled, as well as that you cook… and that you probably cook well. While you may not necessarily have been studying at Le Cordon Bleu, the fact that you were taking cooking classes in Paris is going to imply a number of positive things about you. It’ll also leave a number of open loops and unanswered questions that will intrigue the people you’re talking to. If they know that you the difference between a béchamel and a roux and sauté a mean scallop, they’re much more likely to want to see some of this in action… or to taste the results of your hard work.
The same applies the other skills you’ve been picking up. You can weave opportunities to bring up these topics and stories into the small talk as you get to know someone. Asking about hobbies or interests or what they like to do when they’re not at work is going to be showing interest in them, but it also invites reciprocation. When they turn around and ask you about some of your hobbies, it’s an opportunity to talk about playing sax or ballroom dancing or what-have-you.
The key to remember is that you don’t necessarily need or even want to brag; what you want is to give just enough to get them curious or interested. By utilizing those open loops and unanswered questions, you’re leaving room for them to take the next step and fill in that space themselves. This can come in many different forms, from wanting to know more (close those loops, fill in those gaps by asking questions) to making comments about how they love a sauce béarnaise.
This is a little sneaky but letting them close the metaphorical gap is also an invitation for them to invest a little more in you. The fact that they’re taking this extra step, seemingly unprompted, makes them just a little more likely to want to follow through; it’s a sort of emotional momentum at work. The fact that they made that first step means they’re more likely to take the next – such as saying “yes” if you invite them to karaoke or if your class has an open dance night for newcomers and folks who may be curious to take an informal lesson or two.
There’re also opportunities to invite people to group events that allow you to show off. Inviting someone to a mid-day cookout that you’re throwing for friends or to join you and you social circle at karaoke is less intimidating and asks less of them than, say, a date; going to a group event is easier to say “yes” to without feeling like they’re promising or committing to more than they’re ready for.
The fact that it lets you show off a little like a peacock? That’s just a bonus.
Good luck.
I feel like I need something cleared up that I’m having a hard time with. You’ve written a lot about how a lot of guys are single because they expect a relationship to just fall into their lap. They’re “too passive” and they need to put in an effort. So, I put in effort. I try to meet new people and have good interactions with people. When I do talk to people, I feel like they enjoy talking to me, but in terms of attraction I’m not getting anything. I feel like I don’t meet a lot of people who I would want to date, and when I do, they already have a partner or they just do not reciprocate at all to my attempts at flirting.
It seems to me that just trying to have a good time is never going to get me anywhere in terms of dating, and neither is laser-focusing on trying to get dates. I don’t think women feel threatened by me or that the “vibes” are bad in some way. Clearly, I have good enough social skills for people to enjoy my company. It just feels like people generally don’t see me as anything more than a friendly person, and if I try to express attraction, they don’t really respond to that.
The only demographic of women that seems to REALLY like me is dorky Catholic church girls. I think it’s because they feel safe with me, but my sinful nature excites them in a way that they haven’t unpacked yet. I’m not opposed to dating a religious person, but when I’ve had the opportunity, they always want kids or want to wait until marriage and… well a lot of them are just too innocent for me. I need someone who can say the word “fuck” without having to confess to a priest about it later, and if I tried to get married in a church, the altar would probably burst into flames. There’s a handful of examples outside of that, but they’re always either just not my cup of tea or incompatible with me for very real reasons.
In the latest column, you wrote about looking too hard. And now I’m just confused, because I have to make an effort to put myself out there and meet new people and make new connections. I’ve had to force myself to go out when all I want to do is stay home, and usually I don’t regret doing that, but it’s not getting me dates and sometimes it is exhausting. I feel like I have been “too passive” in the past in that I go into social situations just trying to have a good time without some explicit goal of getting a girlfriend by the end of the night, and now you’re telling me that’s exactly what I should be doing? Like, what’s the balance between trying too hard and being too passive?
Right now, I feel like I’m somehow trying too hard and being too passive. You say I should just focus on making new friends and meeting new people, but those people are hardly ever potential dating prospects. I’m taking on about as much social interaction as I can without it being too exhausting. I just try to put my best foot forward and have a good time, and that hasn’t produced anything in terms of dating. People talk about “getting back into dating”, but I feel like I can’t even start. So what am I missing?
Where’s The Missing Page?
The passivity problem comes in a few forms, WTMP, but they all tend to fall around people not being willing to take the next step – or often even the first one. The common Nice GuyTM behaviors are an example of that passivity; they’re hoping to avoid rejection by never actually presenting themselves as a potential romantic partner and instead build up a romantic connection without having to put in effort or admit that this is what they’re doing. Other examples of passivity are guys who don’t proactively approach people because they’re looking for someone who’s giving such obvious signs that they couldn’t possibly be mistaken. Still more don’t express actual romantic or sexual interest in people – which is to say, doing things like flirting or asking people out on dates.
Even if they do get to the point of asking someone out on a date, a lot of guys – and women complain about this regularly – will then leave the planning of said date to the person they just asked out. Instead of proposing a specific date on a specific day and time, they’ll default to a “so what do you want to do?” or otherwise offload the responsibility of the next steps on the other person. They may not necessarily realize that this is them being passive; they often think that they’re trying to avoid taking someone on a date they wouldn’t enjoy. But it comes off as lazy at best and suggests that they’re likely to be as hands-off or passive in other parts of any relationship they’re likely to have as well.
Much of dating, like much of life, is about finding balance and learning the benefits of timing and reading the room. Part of why I tell people to go out, be social and make friends is that in general, folks don’t like the feeling of being “picked up”; it feels incredibly impersonal, as though they’re just the most convenient option available. This is also why I recommend being social over doing cold approaches – where you’re trying to convince someone you don’t know or just met to go on a date with you. Cold approaches and asking strangers for dates is incredibly inefficient in and of itself, but it’s also not how most people meet their partners. Outside of dating apps, most people meet their partners through shared activities and interests or through mutual friends. By going out, meeting people and broadening your circles of friends, you make it easier to get to know people and connect with them. Getting to know them and letting them know you helps you go from a random stranger to an acquaintance or even a friend; if and when you ask them out on a date, it feels less like you’re trying to pick someone up, but rather that you’re interested in them, specifically.
But just as importantly, while someone may not necessarily be someone you’re interested in dating… they may know folks who are. If and when those new friends invite you to the events and parties they throw, you have an opportunity to meet some of the people they know – people who are going to be easier to connect with because you come pre-vetted, instead of being a complete stranger coming up to them out of the blue… a warm approach instead of a cold one.
Now to dig into doing too much and being too passive at the same time, a big question comes down to this: are you taking the next steps when you meet people and what steps are you taking? When you’re meeting people that you find attractive, how much interest are you showing and how are you showing that interest? Are you doing any sort of mild flirting at all and gauging their response? This is an important part of turning those connections into something that might lead to a date; it works much better if folks understand you think they’re cool and you’d like to maybe make out about it at some point. Light flirting doesn’t necessarily commit to anything, nor does it imply more than initial interest; it’s just a way of saying “hey, I think you’re kinda interesting…” and inviting a response – like a sonar operator sending out a ping to see what’s out there. If you get a positive response back – a little flirting in return – then you know they’re interested. If you get nothing, you have a data point that suggests maybe they’re not interested in you that way. You cdan do another light flirt or two a bit later, in case they either missed it or misunderstood it, but if you continue to not get anything back from them, the odds are good that they’re not interested.
Another aspect to consider is that going out with a goal of getting a date that night puts an absurd amount of pressure on yourself and makes it harder to be authentic with people. Instead of just vibing, getting to know them and seeing if they may be someone you’d click with, you’re setting yourself an intention of trying to get a specific outcome. In those cases, you’re rarely your relaxed, authentic self and instead are more likely to get lost in your head as you try to move things towards a date, rather than engaging with them as a person. It’s one thing if you’re socially experienced and calibrated; it’s another when you’re still learning. Taking the pressure off yourself and just letting the experience be whatever it is makes it all much easier and – paradoxically – increases the odds of an outcome that you want.
Now part of how you can make that happen is to not worry about getting a date and instead focusing on enjoying yourself when you’re talking with people and helping them enjoy talking to you. That’s more likely to make someone want to engage with you further… and that’s precisely the sort of thing that makes it easier to get a date a little down the line.
The best way to get to this point is to make it possible to stay in touch and keep the conversation going. This is another case where you should ask yourself if you’re takin the next step or just letting things end. If you feel like you’re catching a vibe from someone, are you asking to stay in contact – getting a number, adding them on WhatsApp or Instagram or whatever messaging app you use? It’s generally easier to say “yes” to keeping the conversation going, especially if they’re enjoying talking to you, than to get them to say “yes” to a date to someone they just met. Being able to keep talking, keep flirting and generally building that connection means that you don’t need to get that date now; you can build to it without the time limits of someone having to leave or your calling it a night. You may not be getting a date with someone you met that night, but instead you’re laying the groundwork for getting a date later.
This too requires remembering that there’s another step to take: asking someone on a date. This is another place where folks tend to overthink things. As a general rule, it’s pretty simple to organically bring up that you’d be interested in taking someone on a date. My personal favorite methods are to either to pre-sell the date or to tie it to something that you’ve been talking about already that you know they’re interested in.
Pre-selling it entails bringing up future plans that you have – something you’re interested in doing regardless – then later inviting them to join you. So it may look like talking about this band playing at a bar you’re looking forward to seeing or an event being held at a local coffee shop, then later on saying “hey, I think you’d really enjoy $EVENT; would you care to go?” The other option would to be to mention that there’s an event or get together that’s is either related to an interest of theirs or that ties back to something you talked about previously. Just as with pre-selling the date, you then mention that you think they’d like it and you’d love to take them. In both cases, it feels natural and organic and you’ve demonstrated that you’re taking the time to actually plan things through instead of hoping that she’ll take on some of the responsibility.
The last thing I’ll suggest is that I think you may need to check your presumptions about people. I don’t know what Catholics you have been hanging out with or how old they are, but most Catholics I’ve known haven’t been any less reticent about swearing, sex or unfamiliar with ‘sinners’ than anyone else. Many of the ones I’ve dated have, quite frankly, been freak-nasty. If you’re assuming that those “dorky catholic girls” aren’t gonna be down to clown based solely on their religion… well, I think you’ve found one of the sticking points you need to deal with. Try meeting people where they’re at and seeing who they are, rather than presuming that they’re going to be a particular way based on a stereotype that isn’t even accurate.
Good luck.




