Ask Dr. NerdLove: How Do You Talk to Strangers

Hey Doc,

I know you probably get this question of how to talk to people in a romantic since every other day so i’ll try to help you see it from my perspective. So, you’re out in about and you see a cute girl. The location and what she’s doing doesn’t really matter in this case, because this is what goes through my head:

“This is the most busy, most important moment of her life and if you go up to her and interrupt, one of the following things will happen: a) she’ll yell at you and be mad. b) she’ll laugh and make fun of you. c) she’ll gut you like a fish. or d) all three.”

Now I can already hear you and everyone I’ve ever known say that will never happen, and the worst thing she can do is say no. But that’s doesn’t help. I’ve gotten all the dating advice: just be confident, they’re just as nervous as you are (side note, telling a nervous person that the other person is nervous doesn’t help, it makes it worse), etc.

I’ve even tried your breathing and 3 second rule. Doesn’t help. The being confident thing would be easier if i had any success when it came to dating; I’ve approached friends who I developed feelings for and have been rejected every time.

There is one outlier. One time I did approach a girl, it was 10 years ago at a comic shop. My best friend and I were just joking around. One of my jokes made this girl laugh, so after about 30 minutes of my friend practically begging me to talk to her, we approached her. We did a little small talk and we exchanged numbers. She was only in town visiting a friend for a few day,s so we never saw each other again, but she did text me that it was nice meeting me.

(In hindsight, 2 guys approaching a random girl isn’t really a good look)

But I see that as the exception, not the rule. I think it’s pretty easy to guess that my self esteem isn’t the greatest, but to be honest, it’s way better now than it was back then. I see myself so much better now I many ways, but I still can’t bring myself to approach women. Is there anything else I can try to get past this?

Stranger Danger

One of the ongoing themes of this column is the number of people who don’t actually have the problem that they think they have. Sometimes this is because they’re asking the wrong questions. Other times, it’s because the person looking for advice has attributed the cause for their dilemma to some utterly irrelevant and unconnected problem.

You, on the other hand, have a case of “here’s how you can take all the wrong lessons from your experience.”

SD, while your problems are indeed legitimate, the issue here is that you’re taking your experiences and coming away with lessons that are completely inapplicable to the situation at hand. Let’s start with the fact that you’re attributing your lack of confidence to your lack of dating success.

First of all: the reason why you aren’t having much romantic success is because you’re trying to date exclusively on Nightmare difficulty. When the only people you’re approaching are platonic friends you’ve suddenly caught feels for I’m entirely unsurprised you’re striking out. Trying to change a platonic relationship to a sexual one is difficult, especially when there hasn’t been any flirting, any chemistry or even any hint of interest from the other person. In this case, you’re not trying to start a relationship from scratch, you’re trying to recontextualize your entire relationship with this person. It’s certainly possible, but it requires a fair amount of skill and social calibration as well as a pretty hefty amount of experience. If the majority of your attempts at finding dates is hitting on friends, I’m not surprised that you’re striking out every time.

Second: Your lack of success is kind of irrelevant to the issue at hand, because you’re misunderstanding just what confidence is. Confidence isn’t assuredness that you can’t or won’t fail at something; it’s the knowledge that success is possible and that failure may suck… but it won’t destroy you. You don’t build your confidence by succeeding, you build confidence in making the attempt in the first place. Fear + Survival = Confidence.

But here’s the thing: You already know that success is possible. You’ve successfully chatted up a woman before! You even bring it up in your letter: that woman at the comic shop who started laughing at your jokes. The problem is that, once again, you’re taking all the wrong lessons from that interaction. The fact that you’re calling it an outlier is a prime example of this. You didn’t succeed here due to random chance; you succeeded here because you were doing a lot of the things you should be doing when you’re approaching someone. In this case, you made a comment that made her laugh – a good start – then turned and started a conversation with her that lead to your getting her phone number. The only difference here is that you didn’t do it intentionally… and that’s fine. But that doesn’t make this an outlier; it just means that you haven’t processed how this worked so that you can replicate the results when you need to.

So here’s a quick primer on how to approach somebody.

First is what folks call “the opener”. This is the way that you start the conversation. Despite how it may feel, this is actually the least important part of the process. The way you get the conversation going is ultimately unimportant. In fact, the odds are high that the person you’re talking to won’t remember exactly what it was you said. In your experience at the comic store, you used a form of an indirect opener – that is, you started the conversation in a way that wasn’t about your wanting to talk to them. You made an observation that got her laughing, then (eventually) addressed her directly.

Next is the pivot: moving from the opener to an actual conversation. A lot of folks who focus on having the perfect opening line to start a conversation often get hung up here; they feel like they have to stick to whatever it was they said to get the other person starting. Instead, you want to move things towards getting them to participate in the conversation with you. The easiest way to pivot to a conversation is to show interest in them. I’m a fan of “so what’s your story?” as a way of getting them involved; you’re leaving things open for them to talk about their day, about why they’re in that specific place or about what they’re doing in life.

From there, you want to get to know them and ask interesting questions. Not the standard interview questions, but getting their opinions and thoughts and finding out what makes them tick. Find and emphasize the things you have in common, take opportunities to flirt and generally focus on connecting with them.

Then comes the close: exiting the conversation. In this case, if you’re interested in them, then you’re hoping to at least get their number, if not a date. The easiest way to do this is simple: you say “Hey, I have to go, but I’m really enjoying talking to you and I’d love to do this again. How do we make this happen?” Then you have a number of ways of connecting with her. Maybe she’ll give you her number. Maybe she’ll add you on Snapchat or Facebook or Kik. Regardless: congratulations. You successfully approached somebody and got their number (or what-have-you).

As intimidating as this may feel, you need to understand that all you’re doing is starting a conversation. That’s it. You’re not trying to convince this person to run away with you or have your children; you’re just trying to talk to them and see if you’re interested in them… and if they’re interested in you.

Now there are two ways of dealing with your dread of approaching people. The first is to watch for signs that somebody is open to being approached or otherwise not busy. The woman who’s reading intently, has her earbuds in or is working at her laptop in the coffeeshop is likely not up for talking to people. Someone who is distracted, staring out the window or otherwise not concentrating on something? She’s more likely to be open to talking to somebody cool. The best choice, however, are women who’re actively checking you out – who look at you and smile, who’re standing a lot closer to you than is necessary or who are listening in on your conversation.

Y’know. Like the young woman in the comic store.

The other is to stop seeing your interest in somebody as being oppressive or negative. You have a right to find people attractive and to be interested in meeting people you’re attracted to. Cultivating a more positive mindset is going to go a long way towards giving you the guts and the confidence to be more social and start some conversations.

Good luck.

Howdy Doc,

One of my closest long-time friends recently moved back to our hometown, from abroad, following a big break up. She had been dating him for 3+ years and had begun to consider marriage. Additionally, she had an impressively large amount of friends over there and a pretty solid career path. All of that blew up when they broke up as she had moved there for him. Most of our friends from here have moved away and so another friend and I are really the only ones here for her. Obviously, she’s having a very tough time with the adjustment. Now here’s the rub, we’ve hung out a couple of times the past week and I’m catching feelings HARD.

Some background, when we were first getting to know each other, her and I hooked up for about a month back in 2014. It was right after a bad break up for me and I wasn’t even slightly ready to get back out there. I wound up recoiling and ghosting her for a while, something I regret, but we started hanging out again a little later strictly as friends. I was in a bad place and haven’t felt like I could handle any sort of relationship until late last year. I’m really glad that we were able to have that friendship after that. I consider her something like a kindred spirit. I have a lot of friends but very few that I feel really understand me. She’s awesome and I treasure our friendship.

The problem now is that I’ve solved a lot of those problems that shut down my romantic life and my feelings for her are completely changed. I’m intensely attracted to her whenever we’ve been together, something I haven’t experienced with another in years. We’ve always had great chemistry, and the sex was fantastic when we were hooking up, but I haven’t felt anything like this towards her until now. But with where she’s at in her life, I don’t think anything can happen. She’s in a very vulnerable place right now. I feel like she needs friends way more than she needs a boyfriend and I’m one of two friends who can be present. Moreover, the other friend isn’t particularly the nurturing type so, really, I’m kinda it in a lot of ways.

I feel a strong mutual attraction whenever we’re together and it’s really freaking me out. My first thought is to put a little distance between us so these feelings can run their course but I can’t do that as she needs me to be there for her. Ultimately I trust her and myself to get through this somehow but this is pretty intense and conflicting for me.

I guess my question is, how should I proceed with this? I don’t know if I’ll be content with us just staying friends in the long run. I’m asexual with a dash of demisexuality so I move pretty slowly and all of my past relationships have started out as friendships first. Is it disingenuous to be the friend she needs while this feels like the start of something more? Do I need to broach this topic at the risk of compromising our friendship during a time she needs it most? Should we just date, common sense be damned? I am fully vexed.

Thank you for your time,
Catching Feelings for your Sad Friend

It’s not disingenuous to be the friend she needs, even if you’re starting to catch feels, CFYSF. The point where it crosses the line is when you take advantage of being the friend that she needs.

The myth that sex and attraction gets in the way of friendship is just that: a myth. It positions sexual interest – especially male sexual interest – as being this irresistible force that inevitably conflicts with a platonic friendship because folks can’t not act on it. But the truth is: just because someone gives you a boner or the screaming thigh sweats doesn’t mean that you need to do anything about it. Attraction is an emotion, not a command from a burning bush or carved into stone tablets. It’s not that difficult to let an attraction just be that: an attraction. You can notice it, name it and otherwise just let it be.

And to be honest? That’s the best option you have here, CFYSF. Right now, she’s in a really vulnerable place. She’s coming off a bad break up, changing her job, moving back from a foreign country and being separated from her friends. It’s made all the worse by the fact that these all feed into the demise of her relationship. In all likelihood, she’s feeling especially lonely and isolated. This is the worst possible time to be making a play for her. Even if it does work and she decides to start dating you, the odds that it’ll last aren’t great. It’s not impossible… but it’s not great. What she needs more than a boyfriend is someone on her side, who can help support her and prop her up while she’s going through this trying time. If she feels like you’ve been seeing this low point in her life as your chance to hook up with her, then it’s going to be a serious emotional blow… even if that’s not what you were actually intending.

Hey, I get it. You two have some serious chemistry and history together. You’re pretty tight and this is the sort of relationship that lines up perfectly with your attachment and attraction style. Y’all are hanging out all the time and the emotional connection is fairly intense right now. And in other circumstances, this would be a perfect storm for starting something awesome. But that’s not what she needs right now. She needs your support.

So put those thoughts of romance aside for now. Help her get her feet back under her, get some stability and start figuring out what the next stage of her life is going to be. That’s going to be the best and most loving thing you could do for her right now.

The good news is that if the two of you are right for each other? You’ll still be right for each other months down the line when she’s had a chance to heal.

Good luck.

This post was previously published on and is republished here with permission from the author.


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