Why Do I Fail at Finding Friends With Benefits?

Estimated reading time: 17 minutes

Doctor’s Note: Today marks the conclusion of Ask Dr. NerdLove – Revised, as we look back at some questions from the earliest days of the column, answer them from a 2023 perspective and see how attitudes, perspectives and advice has changed in the intervening years.

Don’t forget, if you have a dating or relationship question you want answered, you can send in your questions via the submission form.

This question was originally answered on December 28, 2011

Dear Dr. NerdLove, 

I’m hoping you can help me out. I’m 38, a self-professed geek, and sadly, very single. I seem to be having a problem involving meeting women, that I can’t seem to overcome. I also seem to have another problem in relating to them, once I’m involved with them.

First issue: I was recently talking with some of my fellow geeks, bemoaning the sorry state of my love life, and how I never seem to meet anyone who’d be interested in me, when they dropped a bombshell on me.

As it turns out, according to them, I’ve actually missed several opportunities to get to know women better, simply by dint of not recognizing that they were flirting with me. 

Now, I didn’t recall any times when someone was flirting with me, but my friends insists they’ve seen this happen several times – and have also seen me be completely oblivious to it.

Now, I was willing to blow this off as my friends just messing with me – until I happened to mention the conversation to my mother – and she voiced the same concerns! Having your own mother notice something like this is uncomfortable, to say the least. 

I’ve tried reading articles about how to tell if women are interested in you, but they don’t seem to do me any good. I just don’t seem to recognize any of the cues I’m supposed to see, when I do actually talk with women, which is admittedly, not very often. I am a geek, after all. It doesn’t help that I have ADHD, but I know that can’t be the entire reason for my problem.

Second issue: this involves a kind of long story, so please bear with me.

I was involved with a woman a couple of years ago. We met, got to know each other, and things progressed into a physical relationship pretty quickly.

We agreed, at the start, that neither one of us was looking for a serious romantic relationship. I was still smarting from a break-up a while before, and she had just gotten divorced. So we both stated that we were just looking for someone to have some fun with – “friends with benefits”, as they say.

Well, for a while, that’s exactly how things were between us. We’d get together, hang out, talk, and have fun. Just as often as not, we’d end up in bed together.

However, after about 6 months, things seemed to change. First, she unexpectedly bought me gifts. Then, she started wanting to go out with me more often.

This seemed a little strange to me, given the nature of our agreement, but I went along with it.

However, after a few months, I started losing contact with her. I stopped calling her, and she stopped calling me. Eventually, she moved away to another state. 

I recently spoke to her online, and happened to mention how odd it was that things between us seemed to just come to a halt, and that’s when she told me something I apparently didn’t see for myself – that her feelings had changed, and she wanted things to be more serious and permanent between us. 

She also stated that the reasons she left me were twofold: One, that it didn’t seem to her that I wanted things to be any more serious than when they started; and two, that she couldn’t truly tell how I felt about her. When I told her that I had genuinely cared about her, she was honestly surprised.

A few days after this online conversation, I mentioned it to a couple of friends of mine, one of whom is female, and she told me that the reason my FWB left me was the same reason my last girlfriend before her left – she just wasn’t sure how I felt.

So, my question is: for each of these problems, what would your recommendation be? I don’t seem to be having any luck improving things on my own, and thought a fresh insight could be useful.

Hopefully, I haven’t bored you to tears with this letter.

Thanks for your time.

Blind Guy

Ok BG, I want to start off with asking an odd question: you have ADHD, but have you ever looked into whether or not you’re on the autism spectrum? The two are often co-morbid, and there’re a few things in your letter that strike me as being similar to some of the ways autism manifests itself – specifically, missing some social cues and not recognizing underlying meanings behind actions that seem… kind of glaringly obvious to me and other people.

Now to be sure: that’s a diagnosis for an actual professional to make, not a loudmouth with an advice column. Don’t forget: Dr. NerdLove is not a real doctor. But if you have the time and resources, it may be worth at least exploring that possibility. If nothing else, looking into it may give you answers and explanations, and having an official diagnosis can give you access to support and resources you might not have otherwise.

But for now, let’s assume that you’re the same flavor of neurodivergent as I am. And in this case, that means that you need to look inward and realize how much of this is coming from either an inability or unwillingness to look beyond yourself. Because if I’m being honest? The examples you give in your letter sound like you missed some rather glaring clues that things have changed in your relationships.

Now this sounds like I’m being unsympathetic, and I’m not. I’ve been there and done that, including missing when someone invited me back to her room for a hot cup of “fuck my brains out”. So I hey, I can completely relate and I absolutely understand how that could happen to you. 

My own inability to look beyond my own needs and interests and my own self-limiting beliefs were a pretty huge stumbling block for me in the bad old days. I missed out on people who – like your former FWB – may as well have been waving flags like they’re trying to guide Maverick in for a carrier landing. And that didn’t change until I was willing to start changing how I saw myself, first and foremost.

That’s what’s going to need to change for you, too. Much of the problem is in how you see yourself, which in turn, affects how you see the world around you. Change that, and you are going to see some serious changes in how you and the women in your life relate to one another.

The problem is, however, is that this requires that you’re going to have to put in a pretty significant amount of effort. You’re caught in a series of self-reinforcing patterns that are ultimately not serving your needs. In fact, they’re actively harming your attempts to find relationships.

The first thing you need to do is get over the whole “I’m a geek, therefore I can’t/won’t/don’t talk to women” thing. This is a prime example of a self-limiting belief. You’ve defined yourself as “someone who women don’t like”, much the way I used to refer to myself as “The One Who’s Not Good With Girls”. While I realize this feels like you’re just being real with yourself – spitting those harsh truths, no illusions and all that – what this is actually doing is setting yourself up for failure. It’s a self-perpetuating cycle; you think women couldn’t possibly be interested in you, so you don’t talk to many, especially women you might be attracted to. When you do, the fact that you already think that women aren’t likely to be into you means that you ignore, miss or dismiss any indications that they’re attracted to you. Because you miss those signs, women assume you’re not interested, and since you already think that they aren’t going to like you, you don’t work as hard at trying to connect with them. So you end up missing out on the people who do like you or send the wrong message, focus on the rejections and treat this as proof that they don’t like you.

All of this is a form of confirmation bias; you’re seeing what you expect to see because you already believe that this is the case and write off the things that go against those beliefs as being wrong or irrelevant. So one of the first things you have to do is start to change those beliefs.

Now considering that you’ve had a few relationships under your belt – including one casual relationship that clearly was turning serious for her – this should be an easy lift. “But those relationships failed!” I hear you cry. Well, thank you, convenient rhetorical device, that sounds like the perfect segue to looking at precisely how those fell apart.

You and your FWB started off with a casual relationship. You were recovering break up, she was fresh from a divorce; it makes sense that the two of you wanted something low-key, low investment and low commitment. That part’s fine and dandy. You two clearly enjoyed each other’s company and had great physical chemistry. All of that was great.

Where things started going wrong was at the six month mark, when your pal started behaving differently. Between the unexpected gifts and the wanting to see you more often, it should’ve been a sign that things were changing for her. You even noticed this at the time. The first mistake was that you didn’t say anything; you just went along with it.

One of the important parts of being in a casual relationship – regardless of whether you’re friends or not – is the relationship, and maintaining a relationship means keeping the lines of communication open. It’s good to check in with your partner in general, but especially if your partner’s behavior seems to be changing or they start acting differently with you. Making sure that you’re both on the same page, or that your arrangement is still working for them (or you) are best practices for keeping the “friend” in “friends with benefits”. But if your FWB starts behaving more like a girlfriend and you just shrug your shoulders and roll with it while not otherwise changing your behavior with her? That’s going to send some mixed, and not terribly helpful signals to her. It’s not hard to see why she might not know how you felt.

But then you stopped calling. That is where shit went off the rails but good. From the timeline, it seems like you were the first one to suddenly just quit talking. That’s not cool, my dude, especially if you wanted to keep some sort of relationship with her, platonic or otherwise. One of the biggest sins of a casual relationship is treating your partner casually. Ghosting someone is one thing if you’d only been on a date or two. If you two’ve been hanging out regularly and exchanging bodily fluids, then giving a heads up that you’re ready to end the arrangement is the least you could do. I’ve been on the receiving end of having a FWB suddenly end things without so much as a “hey, Iet’s talk about where we’re at with this” and I can tell you from experience, it hurts and it’s really hard not to take it personally.

Now to drag this back around to those self-limiting beliefs and confirmation bias, I can see how you might not realize that she was developing feelings. It’s easy to ignore signs that somebody’s feelings might be changing if you don’t believe that people could really have feelings for you or like you beyond friendship. And when you’re holding onto those beliefs… well, again, it’s easy to not really know how to express how you feel because hey, what’s the point? You’d be shouting into the void. But if you want a loving relationship – committed or otherwise – then you need to make sure that you’re providing some of that loving and caring, and in a way that they can actually receive. If you’re lost in your own head about it or don’t recognize that what’s glaringly obvious to you might not be as immediately recognizable to them… well, that’s where you’re going to get some serious miscommunication under the best of circumstances.

So what do you take from this, moving forward? To start with, start working on changing those beliefs about yourself. Being willing to accept that women do like you and want relationships with you is going to be an important step for you; if confirmation bias is going to make you focus on the things that align with your beliefs, you may as well choose to believe things that actually benefit you.

The next thing to do is to start paying more attention to the people you’re dating and erring on the side of communication. People aren’t mind-readers, nor are they telepaths; you can’t assume that you know what they’re thinking or that they’re able to read your intentions or feelings with perfect clarity. If you’re not sure how to read the scene or how somebody’s feeling – especially if their behavior seems to indicate that they want to be more than friends with benefits – then ask. If there are ways of communicating with you that help ensure you understand, make sure they know that too; communication only works if the two of you are able to actually understand what the other’s saying, after all.

But just as importantly, make sure that you communicate how you feel, and in ways that they’re going to understand. You don’t say anything about what you and your ex FWB talked about, but it certainly doesn’t sound like you ever told her that you cared for her and God knows your actions said the opposite.

I realize that talking about communication styles or regular check-ins can sound cringey and weird, like you’re an HR chat bot and not a person, but think of it as a “here’s how you can win with me” cheat sheet; you’re giving her the codes to get the good ending to a relationship with you and vice versa.

Even when you’re “just” friends with benefits.

Good luck.

This question was originally answered on December 7, 2011

Dear Dr. NerdLove:

I have a situation that I’m looking for answers for and I hope you can help me out.

I meant this guy through my mom, he was college student completing his masters at the time. My intentions were only to become his friend, so my girlfriend and I hung out with him the first at the movie theater. He totally came off serious, very direct and nervous. I know other people including my girlfriend labeled him as a “serious-nerd”; however, I saw past that. In fact. I found him interesting to get to know and be around.

So I invited him to a cultural event in which he decided to attend with me. He enjoyed it! As weeks progressed we would continue to make plans together such as hanging out at cafe’s or checking out city attractions. I would always invite my girlfriend, so she started building a friendship with him too. So, I had thought it would be a good idea to have them hang out more often alone, so I would make arrangements to allow that. I had felt that my motive was good because they both communicated so well, and shared similar behavior and perspective toward health and fitness.

As weeks progressed, he would always offer his assistance such as taking me to work, picking me up for workout sessions, take me to lunch, helping my family out during the time my mother had transportation problems, taking my mother to work @ 4 am in the morning, and not to mention less than 2 months in our friendship he helped me out pay for a bill. I was really surprised in how generous and caring he was for my mom and I.

This is where my suspicion kicks in, he brought up a conversation with me about my mom having us meet because she was hoping something romantic would evolve. This struck me with confusion and I felt slightly awkward because personally my mother would definitely confide in me if she’s playing matchmaker. I told him ” well we don’t really have things in common and that you are in a different stage in life, you have a lot going on in your life” (He started speaking very fast so I figured he was nervous) He told me: “We have things in common that’s why were friends if we didn’t we wouldn’t even be friends. I hope your not thinking of the stuff I did and think I’m hitting on you because I’m not.” I just reassured him that I like meeting my mom’s co-workers or friends. I know my answer was nonsense but I really didn’t know how to answer that at the time.

Since then, I have been thinking of that conversation and realized that I’m beginning to have feelings for him. He has done so much nice things for me, recently he took me out of town to a place I wanted to visit, he just spontaneously called me the next morning and asked to take me there so I went for it! I’m still learning how to read him, so I don’t know if he likes me more than a friend or just a generous friend who is trying to help out.

I know I’m oblivious to the signs of interest from a guy because personally I don’t have that much experience to begin with. So any advice or suggestions would be welcomed!

Lost In The Moment

I could parse all of his behavior out with you, LITM, but honestly, I don’t know if it’d help you as much as you’d prefer. I mean, we could go through every single thing he says or does, check for every intonation or stressed syllable, compare his behavior with you versus the other people in his Masters program or at work, but at the end of the day, this would be a guess. He could be madly in love with you or he could be someone who is incredibly generous and giving with his friends, almost to a fault.

But there’s really no need.

I’m going to be real with you LITM: I really can’t stand trying to read the tea leaves when it comes to figuring out how people feel. I spent far, far too much time doing that in my life and all it ever did was waste time and give me anxiety, no matter what I thought the ultimate answer was.

As it turns out, there’s a really easy way to figure out whether somebody’s interested in you as more than just a friend or not: you ask them out on a date. Not asking them “how do you feel about me” or confessing your feelings to them, but asking them out on an actual date. Not to hang out, not get together some time, but a date. Making it clear that it’s a date, on a particular day and time, for a specific activity. That they understand is a date.

Here’s the thing: a lot of trying to parse meaning, reading between the lines or just trying to divine intention from what they say or do is a fruitless endeavor. We tend to do this because we’re afraid of rejection. We want to try to figure things out in advance because asking someone out means that you’re making yourself vulnerable to them and it feels safer to hold off until you’re 104% sure that they’re going to say “yes”. But honestly? All this does is waste time – yours and theirs – and just creates more anxiety.

Every single thing that could signal romantic or sexual interest could just as easily be interpreted as having platonic explanations, especially if you’re prone to overthinking and over-analysis. It’s entirely understandable that you (the generic “you”, not you specifically, LITM) would want to protect yourself by not risking heartbreak or worse. But the fact of the matter is that love, like skiing, means assuming the risks. You can do your best to mitigate them, but you can’t eliminate them entirely. If you’re going to participate, you do so with the understanding that you could get hurt and you accept that the rewards are worth the risk. And the longer you try to avoid the risk, the less time you have to enjoy the rewards.

Now, why am I saying “ask him out on a date”? Because it means you’re taking action. I’m not a fan of just telling someone how they feel or asking how they feel about you, in part because what you’re functionally asking is for them to make a decision about the kind of relationship they want with you, right then and there. That’s… a lot to ask for, especially if you’re not sure how they may feel. A date, on the other hand, is understood to be the start of figuring out whether or not the two of you are interested in each other or even if you’re compatible. It’s a much easier lift; you’re asking for a couple of hours together to see if there’s more between you than friendship and if you want to go in that direction.

Asking someone on a specific date gives them something to say “yes” to. Getting together “some time” or “hang out” are so nebulous – and in your case, so close to what you already do – that they’re functionally meaningless. Plus, when you ask them out on a date, the “I like you as more than a friend” is part of the ask. Folks rarely ask people on dates if they’re not at least a little into them, after all.

So my advice is, if you’re digging his company and he seems to be enjoying yours and you’re starting to catch feels for him? Worry less about reading the signs or trying to untangle this particular knot and cut straight through it. Ask him out on a date and see what he says. He’ll either say “yes” and you two can start something amazing, or he’ll say “no”. While that may sting, at least the matter will be resolved. One way or another, you’ll get an answer.

But if you were to ask me to wager actual money on it? My bet would be “he’s going to say yes”.

Good luck.