DEAR DR. NERDLOVE: The guy I’ve been seeing for the past three months is still very close with his ex; they ended things a year ago. They dated for 3 years after having a strong friendship prior to their relationship. The ex tells the person I’m seeing incessantly that she wants to be back together with him and guilts him if she feels he isn’t “supporting” her. 

They recently went on an overnight trip together to one of his friend’s birthday parties a few hours away and are planning a weekend trip together to see one of his sick family members in October. Evidently, she became very close with his friends and family during their relationship (though half of it was during the pandemic so it’s all a bit confusing for me). I brought up that I felt going on a long weekend trip with his ex was crossing the line. He responded he could understand if there was even a hint that something could happen between them, but he knows nothing will and just wants her to return to being a good friend. However, if she’s around it doesn’t feel like I’m welcomed.

I don’t think there’s room for the relationship with him and me to grow if he’s constantly prioritizing his ex, and their relationship seems unhealthy and codependent to me. I’ve brought it up and he’s unwilling to budge, saying she’s very important to him and he’s trying to navigate a difficult situation. I feel like I’m being reasonable and not controlling, but he said he couldn’t imagine being with a partner who controls who he sees and who he doesn’t, even though what I actually said was that he needed boundaries that defined the relationship with his ex appropriately.

Thoughts?

Ex Wrecks

DEAR EX WRECKS: There are two very different problems here, EW, and they require different approaches.

First there’s your boyfriend’s ex. What she’s doing is not cool. It’s disrespectful to you, it’s disrespectful to your boyfriend and she’s clearly either missing or choosing to ignore any and everything your boyfriend’s doing to try to get her to back off. I can appreciate that he seems to be trying to thread a needle with her and avoid having a direct confrontation about this so as to preserve the friendship… well, some direct confrontations are unavoidable and need to happen. Especially if he wants to stay friends instead of needing to cut her off.

In this case, what your boyfriend needs to do is to lay down some pretty firm boundaries regarding her behavior. He needs to say “I’m glad we’re still friends, I value our friendship and I want it to continue, but we broke up. I’m not interested in getting back together with you, I don’t want to hear about you wanting me back and I don’t appreciate your trying to leverage our friendship in order to get me to do more with you. If you don’t stop acting like this with me, don’t stop disrespecting my relationship and don’t stop talking about wanting to get back together with me, we’re not going to be able to be friends going forward.”

And he needs to say that directly, clearly and without softening the language or giving her any sort of plausible wiggle room. There can’t be any euphemisms that could be misinterpreted, any vague language that doesn’t spell out exactly what he’s telling her to stop doing or any question that what he expects is for her to act like his friend and not some third tier stock character from a bad mid-90s boner jam. He needs to be very clear: their friendship continuing is entirely contingent on her changing her behavior.

If she says she’s not trying to guilt him or get him back then his response should be “Great! Then you shouldn’t have any problems continuing to NOT do that,” and be willing to call her out when she (inevitably) does. A quick “That? That thing you did? That is exactly what I want you to stop doing,” will drive home that he’s serious about this and isn’t interested in whatever weird games she’s playing. Even if she tries to weasel around it – “but that’s not doing X!” – then either he can add it to the list of things to stop doing or he can call her out for acting like a ten year old and treating him as though he’s so stupid as to believe that.

And to be clear: he needs to be doing this for himself. Not for you, not for the sanctity of his relationship with you but for him. This is behavior he should not be tolerating from people he’s allowing to be part of his life, regardless of their past or current relationship, and holding strong boundaries is how he prevents people from running roughshod over him.

Just as importantly, he needs to be willing to enforce those boundaries. If he lays down the law here and says “enough, stop it or else” and doesn’t followup on the “or else” part where he walks away? Then all he’s done is made it clear that those aren’t boundaries, they’re suggestions, and she doesn’t need to take it seriously. When someone doesn’t enforce the boundaries they establish, they make it that much harder to get people to respect any of their wishes, since clearly they’re not going to follow through.

Now that’s the first problem.

The second problem is, well… you and your relationship with your boyfriend (and by extension, his ex).

Here’s the thing: the issue with your boyfriend and his ex isn’t that he’s friends with his ex or that he still has a close relationship with her. The issue is her post-break-up behavior. She’s being s--tty about things and being disrespectful in the way she’s acting, but that doesn’t make her a threat to your relationship. The fact that you don’t seem to trust your boyfriend, on the other hand, is a threat to your relationship. That’s going to be a much bigger issue than how she’s acting.

The issue I have at hand is that other than the aforementioned open stating of her wanting him back – which I agree, is over the line and he needs to pull her up sharp over this – is that it doesn’t sound like there’s anything else going on. Not, at least, in what you’ve written. I don’t know if it’s that there isn’t much that you can point to directly, or if what seems clear to you isn’t coming through in the letter. But that lack of examples is making it difficult to judge that there’s anything going on besides vibes.

For example: nothing in your letter makes it sound like he has even the slightest interest in being with her again. While, as I said, he definitely needs to lay down some boundaries with her, it sounds like he’s currently trying to thread the needle of maintaining a friendship that clearly has value and meaning to him. That’s entirely understandable. The fact that they broke up doesn’t mean that he is now obligated to act as though the years of friendship and the years they dated no longer matter, nor does it mean that he needs to cut her out of his life. As a general rule of thumb: people who maintain good relationships with their exes – whether they’re just cordial and respectful or remain close friends – are folks who are demonstrating that they’re emotionally mature and intelligent and are generally sold individuals. If anything, it should tell you something about his character that he still has that affection and respect for her, even if his tolerance of her current behavior isn’t helping him or you, nor is it covering him in glory.

But that’s why my question to you is: what threat is she actually presenting to your relationship? What about his behavior is unusual or challenging that isn’t adequately explained by “close friends for years prior to dating, and are still close now”? Does he have a prior history of cheating, lying to you or otherwise acting shady, especially around her? Do you have reasons – beyond their previous relationship – to think he’s particularly vulnerable to her blandishments? Or do you trust that he’s perfectly willing and able to say “no, stop that” if she starts trying to get frisky with him, but the idea of him being alone with her is giving you the wiggins?

If there’s reason to believe that he’d hook up with her if given the chance, then yeah, that’s an issue and needs to be handled if there’s going to be a future for the two of you at all. But if you don’t trust your boyfriend to not refuse her advances while on a trip, especially without a stronger reason than “opposite gender people on a trip together”, that’s more of a you problem than a him problem.

Similarly, you haven’t really given me much to go on with his prioritizing her over you, beyond not being willing to cut her out of his life. If there’s something more than that – maybe he’s skipping dates with you to be with her, especially over trivial matters – then yeah, I would agree that this is a problem. But based solely on what you’ve written? I’m not seeing that.

The same applies to what “doesn’t make you feel welcomed” means in this case. Is it that they’re actively shutting you out or mocking you? Or is it that many years of friendship means that they have history and inside jokes and the like that you aren’t privy to?

The last thing I wonder is what “boundaries that define the relationship with his ex appropriately” means. That’s an incredibly vague way of phrasing things, and it doesn’t really say what you’re asking for. If you phrased it that way to your boyfriend… well, honestly, I couldn’t blame him for thinking that you were saying “cut her off” without actually saying the words.

So, absent that info, I can only say this: it’s entirely appropriate to ask him to tell his ex that she needs to knock off the “I want you back” talk. I fully agree: he absolutely needs to do this and it’s not good that he hasn’t. I don’t think he’s avoiding doing so for sus reasons so much as trying to navigate a treacherous path, but as I said: it still needs to happen. But for the rest? I think it’s important for you to examine just what is bothering you and to be able to communicate it clearly and directly. If you’re feeling like you need some more attention or reassurance of how he feels then by all means ask for that. If you’re worried that he still has feelings for his ex, then tell him that’s what you’re worried about. But if you have a specific ask for him about how he treats his ex or the time he spends with her, then you need to say that too, and not couch it in terms like “define the relationship with his ex appropriately” because what you think is appropriate and what he thinks is appropriate clearly vary. People often rely on “well everyone knows what that means”, when very obviously not everyone shares the same definitions of “appropriate relationship”.

This is especially true when you’re talking about a friendship of years – even prior to their dating.

However, if what you actually mean is “stop seeing her so often” or “stop seeing her alone”, but you don’t actually want to say the words out loud to him? Well, that puts you in the same boat as him for not telling his ex to knock her bulls--t off.

Good luck.

Please send your questions to Dr. NerdLove at his website (www.doctornerdlove.com/contact); or to his email, doc@doctornerdlove.com

DEAR DR. NERDLOVE: I (M/26) in a reasonably large American city, and I am trying to get seriously into the dating scene. I looked around your site and your post about The Grimes Test has left me feeling down about myself since it drives home something I’ve known about myself for a while. I’ve got a place to live, I’ve got a job, I more or less have the responsible adult skills package down so I’m able to mostly handle my financial obligations. But my life is “TFW No Girlfriend” writ large.

I don’t really know how to lead up to a question like this so I’m just going to say it: I’m boring. I am dull. I am less interesting than C-SPAN reruns on a Sunday afternoon. My job is a 50 hour a week cubicle drone, my car is reliable and that’s about it. I’ve got some coworkers I get a drink with, I’ve got a couple friends post-college that I see occasionally. But there’s nothing interesting about me. My hair is ‘hair colored’ at best, my eyes are ‘yes he has some’, my body is functional and my facial features are I guess a solid C. There’s not really anything else about me to get a woman interested or inspire her to talk to me. I don’t even have anything like good “bad” tattoos or something. If I go out to the bar or the club I’m lucky if I even get served never mind get any of those signals you talk about from women. Women DEFINITELY don’t come up to talk to me unless it’s to ask to pass a napkin, and I can’t even muster up the enthusiasm to try to talk them into talking because what are we going to talk about, my mostly nondescript apartment and a used Toyota Yaris?

I guess if I wanted to be all weird internet loner I could claim I was a skilled “gray man” or whatever the f--k some TikTok video talked about but I’m not. I’m just occupying space and waiting to occupy a coffin in 60 years. How do I get to be interesting so women will actually be inspired to talk to me for more than just convenience or because I was in the way and they hadn’t noticed?

Oops I Didn’t See You There

DEAR OOPS I DIDN’T SEE YOU THERE: Alright OIDSYT, let’s start off with a mistake that a lot of folks make, especially when they don’t have much dating experience. A lot of people – mostly, but hardly exclusively men – get hung up on the initial phase of meeting people and finding dates. They’ve gone all-in on the attraction phase of meeting folks; that is, they’re mostly concerned with the very beginning of the relationship. Now to be fair, this is understandable. If you’re someone who has struggled to meet amazing women, whether in person or on dating apps, just getting to the point where you’re receiving lots of (wanted) attention feels pretty significant. And honestly, most of us kinda like the idea of being someone who just rolls up and suddenly all eyes are on you; women want you, men want to be you and here you are, just able to bask in the glow of knowing you’re the focus of everyone’s interest.

But the problem is that the folks who are the most hung up on getting that attention or attraction are incredibly short sighted. They’re stuck in a pattern of short-term thinking, focused on getting over their initial hurdle of “well I don’t know how to talk to women” and “women don’t show interest in me ever” without ever thinking about what comes next. They assign all their points to try to get through the early stage without realizing that attraction means nothing if you don’t have anything to follow it up with. Hell, in some cases, they never even consider that dating or having a relationship would mean actually doing stuff that isn’t just “look over next to me and see someone pretty in the room while I do my usual routine”. So what ends up happening is that the folks who zero in on the attraction phase tend to be all sizzle and no steak.

Occasionally, there isn’t even sizzle, so much as somebody playing an MP3 of someone else’s steak cooking.

There’s a difference between being attractive, and being someone people want to date. The former doesn’t get anywhere without the latter… but the latter is what helps build the former. The key, however, is understanding how.

Thanks to capitalism and an incredibly catchy marketing campaign, we all have the image of The Most Interesting Man in the World sitting at a table at a bar or lounge, surrounded by admirers. It’s easy to think that the state of being interesting is all it takes to get there and get those results. But the fact is: there’s nothing passive about it. Being interesting and living an interesting life is the opposite of being passive.  What folks aren’t seeing is what leads to sitting at that table, surrounded by people hanging on your every word and wanting more.

(Well that and, dude, it’s a commercial. Don’t base your life off of a beverage company that just wants to sell you beer.)

Here’s what folks misunderstand about living a cool or interesting life: it requires that you put an active hand on the tiller and consciously steer your life where you want it to go. The fact that you’re boring or live a dull life is, in many ways, a choice you are making every single day. Each day you have a series of choices, and if you use those choices to do the exact same thing, then you’re never going to get out of that rut. And if those are the choices that are the easiest, most convenient or the most comfortable for you… well, that’s great, but that’s also what’s brought you to this place, where you’re not happy or satisfied.

As I’m often saying: if you want different results, you have to do things differently. And if you want to do things differently, you have to start taking direct control over your life instead of just repeating the same loop over and over on autopilot. You have to live like you actually give a damn. People who are dull or uninteresting (and unhappy about it) tend to be people who live life passively. They don’t explore, they don’t enquire, they don’t branch out. If you want a life less ordinary, then you have to spit in your palms, pick up your axe and your hammer and start building it yourself.

Now the good news is that there’s a quick and easy way to jumpstart your life to be less staid and more interesting. You have to engage your curiosity. Part of what makes people dull and uninteresting is that they are following a continuous loop, doing the same things and getting the same results. Engaging your curiosity, by necessity, breaks that loop. You always take the same route to work? Well, what happens if you go a different direction? The seemingly small act of taking a different path to the same place can open up a staggering number of opportunities – you end up seeing new neighborhoods, different stores and attractions, different restaurants, even different people. Each and every one of those is another chance to get curious and break the loop. Eat in a restaurant that you never go to because you keep defaulting back to the same old same old, and eat something that’s not typical for you. Check out some stores that aren’t just major chains, hit up attractions and points of interest that you keep passing by but never actually go into. You might vary your routine by taking a pilates group class at the gym instead of just hitting the treadmill, or join an outdoor biking group and doing some trail riding.

Another way that your curiosity can make you more interesting is to use it to learn new things. Maybe the weekend would be a good time to take classes in a new language, how to cook Indian, Mediterranean or Filipino cuisine or to learn how to dance. Or maybe you’ll go really far afield and try something that’s outside the box. A few weeks ago, I attended a knife-making workshop and learned how to use coal forges and traditional blacksmithing techniques to make a knife from a railroad spike at a living-history park. You might go in for learning lockpicking, or how to navigate with just a compass and a paper map or how to repair a vintage pinball table… skills that may not have immediate relevance or utility in your life, but you picked up just because it seemed neat.

If you can travel, then go places beyond the norm – the off-beat, the unusual, the quirky. That doesn’t mean that you have to go overseas to exotic locales, mind you. You don’t have to go to Bali or Ankhara or Petra if you want to be interesting. Even if you don’t leave the country – or your state or your county – there’re more cool, different or non-traditional places to visit and things to see. Go do the weird roadside attractions, visit the obvious tourist traps and take detours because they seem cool at the time. Hell, do some of the tourist-y s--t in your own back yard; act like an out-of-towner and go do the things that you turn your nose up at because you’re a local. Collect experiences simply for the sake of having them.

Not sure where to start or where to go? Well, again, this is where taking an active hand in your life comes in. We live in a world of unprecedented access to information, and there’re more resources for finding events, restaurants, shops, classes, opportunities and hidden gems just in your hometown than you ever dreamed. Take some time, browse the local alt-weekly newspaper, sign up for Eater or HiddenCity updates, local Facebook groups and subreddits and learn about everything you have around you that you may never have even known about.

And just as importantly: talk to people. Not just folks you’re attracted to, or people you’re trying to network with, but just people. Get curious about folks, what they do, how they do it, what they think. By just being interested in folks and being open to possibilities, you dramatically increase your odds of interesting things happening. Whenever I’ve decided to just talk to folks, I’ve had some incredible experiences and met amazing individuals who had depths and surprises you could never imagine just by looking at them – treasure hunters, shipwreck divers, soap opera actresses, travel facilitators, you name it. And by having some unusual or unique or just off-beat experiences in your life or making interesting or different choices, you end up having stories to tell and knowledge to share.  That means that you are, likewise, the interesting person that other folks had the good fortune to meet.

It’s a lot easier to carry on interesting, captivating conversations when you have a broad base of general knowledge as well as a deep well of stories to share, after all.

But let’s bring things back around a bit to how this makes you more attractive and improves your dating life. And for that, we’re going to circle back to the image of The Most Interesting Man in the World. See, rememeber what I said about not seeing what lead to his being surrounded by admirers? Well, what gets him there is that by leading an active life that required talking to people, taking chances and not living a passive life. See, part of why The Most Interesting People are popular is that by doing all of those interesting things and taking all those chances, they’re building connections and networks. You know how in the movies, Indiana Jones seems to have contacts all over the world? Those happened because he actively seeks people out, focuses on getting to know people and building relationships. Interesting people are interesting in part because they’re deliberately cultivating relationships with all sorts of folks, and they’re doing so by taking the initiative, rather than waiting for Interesting S--t to happen to them. And when they build those networks and relationships, they build reputations as well. Those reputations often precede them because hey, people talk, and they love to talk about the cool people they’ve met recently.

So by the time The Most Interesting Man is at the lounge, many folks already know him. And the ones that don’t are the people he met that night and invited them over. It’s not that he showed up, sat down and waited; everything about his popularity is the result of his actively engaging with people, both that night and all the nights before. Hell, his BEING interesting was an active series of decisions, choices and intention. It was built over time through sweat, effort and perseverance.

To be sure, that’s an extreme example – and a fictional one at that. But at the same time, it serves as an example of what you could be capable of achieving if you put your mind to deliberately getting out of that loop you live in.

So as I always tell people who tell me that they fail the Grimes Test… well, what are you going to do about it? What are you willing to do to cultivate an interesting and satisfying life? Life isn’t a spectator sport. If you want an awesome life, you have to get out on the field and make it happen. If you feel like you’re boring and nobody would be interested in you, then that’s a choice. Today’s your opportunity to change that and make a different choice.

It’s all up to you.

Good luck.

Please send your questions to Dr. NerdLove at his website (www.doctornerdlove.com/contact); or to his email, doc@doctornerdlove.com

DEAR DR. NERDLOVE: I’m writing to you today because of an issue that I’ve never been able to conquer. The issue is that I’m 33 years old and I have never approached a woman in my entire life, in public or any socially acceptable place. I think that I’m a pretty good catch but I’ve always had issues with my self esteem and my looks. I’m someone who goes to the gym 4 times a week and is trying his best to have a killer body. I’ve never been confident in my looks and I’ve never been confident in my social skills.

Lately I’ve been going to some bars that are close by. They are sports bars and I’ve been practicing eye contact and social skills with the bartenders. Though I don’t flirt with them. It’s just something I do in order to feel more comfortable around women.

When it comes to my side of the bar, where is patrons enjoy our drinks. I can never get myself to muster up the courage to either make eye contact or approach an attractive woman I see. No matter how many years I’ve been going out. I’ve never approached a woman or tried to hit on her or have a conversation. I’m honestly afraid of them possibly being grossed out by me or creeped out by me trying. Though I’m not trying to hook up immediately. I do wish that I could get over this hurdle so that I can eventually have a sex life again. I haven’t had sex in 3 years and it’s really starting to wear down on me. Maybe not so much sex but the intimacy and the dynamics that come from flirting, attraction and hooking up. The entire ritual is missing from my life and I honestly feeling like I’m missing out on an experience that many men have already managed to conquer.

I have my own place, a good career, I have some hobbies and I’m very low key and I’m minimalist. I don’t make 6 figures but I make enough to get by in the world. On paper I’m essentially good to go but in person it seems like I lack any confidence or even courage to go up and try to talk to women. I’d love to have a sex life again, I’d love to learn to flirt and I’d love to stop being afraid around women I find attractive. How do I change this entire mindset? What mindset do I have to be in exactly? How do I feel like I can just do it… and then actually Do it!

I hate to say that I’ve started even looking at paid PUA books and videos but they honestly seem to promise too much but at the same time I’m so desperate to just be a normal guy and be able to approach and flirt with women that I’m considering possibly buying these things. Even tough a part of me doesn’t believe they’ll change anything.

I just need some tips or something. I’m honestly getting older and it’s just embarrassing that I have such a struggle making eye contact and even going up to talk to women. I don’t want to end up 60 and alone and never have tried. What can I honestly do?

Signed,

Averting Eye Contact

DEAR AVERTING EYE CONTACT: Here’s the thing AEC: you’ve got a lot of good qualities and a pretty solid base for a good life. The problem is: none of that ultimately matters. Not for your immediate goals, anyway. See the thing is, your hobbies, your career, your own place, even your body to an extent… all of those are things that people aren’t going to draw people in. Those are the foundation for a good life, but nobody’s going to know you have them at a glance, nor are they going to really influence who’s going to want to talk to you or who you should talk to. There will be folks who’d be glad to know you have those – being a functional adult is a low bar to clear, but a lot of folks don’t manage even that – but that all comes later. And none of it’s going to imbue you with confidence or assertiveness by virtue of transitory properties of Having Your S--t Together. Certainly not in the way that you suggest in your letter.

You have two things that are holding you back right now. The good news is: it’s all in your head. The bad news is… since it’s all in your head, that means there’re no quick and easy fixes. It’s going to require a willingness to roll up your sleeves and get down to the messy business of uprooting negative patterns and expectations and good old-fashioned practice until things become natural to you.

As I said recently, confidence is born out of knowledge and experience. You can have things in your life – like a car or jacket or other material goods – that serve as a magic feather of sorts, allowing you to unlock the confidence you already have by making you feel like you have permission to be confident or to feel like you’re cool. But if you want actual, meaningful confidence and to feel like you can actually do the things you want to do – in this case, talk to attractive women and maybe get a date? Well, there’s really only one way to accomplish that: you have to actually go out and talk to people.

The issue isn’t whether you can do it; obviously you can. If you couldn’t go talk to people, you’d have a much harder time navigating the world, never mind doing things like holding down a steady job. The issue is that you don’t do it. And that comes down to expectations and fear. And fear, as the litany goes, is the mind killer.

Now, the fear aspect of it is obvious; you’re afraid of rejection, you’re afraid of being hurt and you’re afraid of humiliation. That’s ultimately what a lot of the fears of being called “creepy” come down to: how it’s going to make you feel and what the consequences will be if make a mistake. And like I told A Confused Asexual the other day, that fear is ultimately a form of self-protection. After all, our brains and our instincts are about keeping us alive and safe; happiness, romance, sexual fulfillment… those are all secondary considerations, if they ever come into the equation at all. So part of what you need, in terms of changing your mindset, is to recognize that the fear that’s keeping you from actually talking to women is a pattern of behavior that no longer meets your needs.

Your expectations, on the other hand, are how you look at yourself. This affects those patterns of behavior, in as much as you have a hard time believing that anyone would enjoy your company. If you were more assured of your own sense of worth, your own sense of value, then you wouldn’t have the expectation that you “should” have done this already, nor would you be as sure that you need to do everything perfectly or risk being labeled a Creeper and risk becoming a pariah. That same feeling – needing to know “what to do” and having a technique or formula to follow – is what leads folks to pick-up artists, red pill grifters and the like. Having some material you can rattle off at the drop of a hat or a sequence of things to say to women is a sort of confidence substitute, a temporary patch to get you off your ass and into the game. But, as someone who’s been in and out of that scene, I can tell you from experience: it doesn’t work for long, and won’t help you where it counts. Talking to women, flirting, building attraction, etc. are just the start. They’re what get you in the door. If you don’t have that sense of your own value at your core, then whatever you generate will be temporary at best, and the insecurities and fears will just come raging back and kick over everything you’ve been trying to build.

But here’s the thing. Remember what I said about confidence being born out of knowledge and experience? Well, fortunately, the thing you’re trying to be more confident in is fairly simple. You open your mouth and flap your gums. You say that you’re not looking to get a hook-up or whatever and hey, that works wonderfully for our purposes, because what you need right now is to just get to the point of talking to strangers without worrying about it. This works to your advantage, because it means that just about anything is a positive result. If you were to go to the bar tonight and make brief small talk with some of the other patrons of any gender, then you’re building that experience and getting yourself one step closer to your goals.

One of the things that made my life a lot easier, as well as improved my nights out, was learning to let go of expectations. I would prime myself for a good night in two ways. First: I’d have a social warm-up – talking to a friend or family member before I went out on the town. Think of this as shifting from “work” mode or “quiet and shy” mode and into a social headspace. Just as you want to warm up before exercising, limbering up those social muscles and getting yourself in a more talkative mood makes it easier to actually strike up conversations with people. Otherwise, you end up expending a lot of your mental and emotional bandwidth just trying to shift where your head’s at and work up the drive to talk. This always ends up taking longer than you think it will and it leaves you with far less gas in the tank, as it were. So a social warm-up, even if it’s just a phone call or video chat with friends, goes a long way to getting you ready to be social with strangers.

(Notice very carefully that I keep emphasizing friends and loved ones. The social mode you’re in at work or talking to co-workers that you don’t also have a friendship with isn’t going to help you here.)

The second thing that I would do to set myself up for success was to reframe my goals for the evening. When I would go out, whether at home or if I were traveling, I went out with a mindset that somewhere out there was An Adventure, something that would be the story of that night. That adventure could be anything. It could be finding a cool new bar or an awesome new restaurant to try. It could be finding a new, interesting nook or corner of town I hadn’t seen before or looking at it from a different perspective that gave me a new appreciation for what was around me. It could be talking to a fascinating stranger – or many people – and hearing awesome stories from folks I don’t know. Or I might meet a sexy somebody, maybe exchange numbers or maybe see if anything else were likely to happen. But whatever happened… there would be A Story before the night was over.

Because I wasn’t setting myself up for something I could fail at, I would go out with a more optimistic mindset and keep myself in a good mood for the night. By creating that expectation that something good was waiting for me out there, no matter what, I was encouraging myself to look at the world with curious and hopeful eyes and priming myself to take chances, try new or different things or otherwise get out of my usual routine and see what I might find if I decided to zig instead of zag.

So I’d recommend adopting this outlook for yourself, AEC. Warm up socially first, then go out with the expectation that somewhere out in the night is an adventure, and you have no idea what that adventure may be. Get curious about the other folks at the bar; assume that there must be something cool or interesting about them and see if you can find out what it might be. Encourage others to be part of that sense of exploration by getting recommendations or suggestions of things to try, whether it’s a new drink, a new restaurant, something interesting happening later that week… anything that is new and out of the ordinary for you.

Now here’s why this will help you build your social skills and make you feel more confident: because having that “there’s a story out there” mindset, you’re leaving yourself open to all possibilities. It means that you won’t have any expectations outside of “talk to interesting people”, which in and of itself, means you’ll be giving a much friendlier, lower-key vibe than someone who’s just trying to get into a woman’s panties. Having a low-stakes, low-investment conversation with someone who’s interesting (and, yes, attractive) is the reward in and of itself. Similarly, it’s priming your brain to not see things like “getting rejected” as an end, but rather a pivot point, a place where your story for the evening takes a turn and leads you in a new and potentially interesting direction. Yeah, being turned down stings, but if you’re looking at it as part of the story of the night… well, it’s not so bad at all. Especially since it’s coming as part of your being willing to put yourself out there and do things you’ve never done before. Plus: it’ll help teach you that rejection isn’t nearly as bad as you fear, nor that you’re doomed to just be a creeper.

Do this a couple times a week and before very long you’ll realize that talking to people – not just women, but people – is something you just do. You’ll get used to showing interest in folks, which makes you more interesting to them; after all, most people (especially women or femme-coded non-binary people) aren’t used to folks actually listening and taking in what they have to say. And as you get comfortable and more confident in your social skills, then you’ll be more comfortable taking things to a flirtier or sexier level when it’s time. Not to mention, you’ll be more successful, because social skills are skills, and you improve them through use and deliberate practice.

But again: none of this can happen unless you actually, y’know. Talk to people. So, make a point to start getting conversations going. Use the classic Plausibly Deniable Opener by making an open-ended statement when you’re sitting at the bar or have a “I’m sorry, I couldn’t help but overhear” moment when someone’s talking near you. Make a comment or pay someone a compliment on something that they chose – their clothes, tattoos, things that they had a hand in. Get curious about the people around you, and you’ll feel more empowered to get to know them a little.

The more you do it, the easier it becomes.

And hey, those adventures you’ll find yourself going on and the stories you’ll end up collecting? Those’ll make you a more interesting person, with more things to talk about… and leading to more people wanting to talk to you, too.

Good luck.

Please send your questions to Dr. NerdLove at his website (www.doctornerdlove.com/contact); or to his email, doc@doctornerdlove.com