How Can I Stop Sabotaging My Relationships With Women?

Estimated reading time: 14 minutes

Hi Doctor,

I’ve had a pretty rough run of my love life for the past 10+ years. My work and social life hasn’t been much better, and recently I made the decision to go back to school to get a second degree. It’s been a positive experience, and my social circle is a lot larger than it had been previously, though I still find myself lonely and wanting for a romantic relationship. After spending almost a decade depressed and closed-off, I find myself plagued by the usual suspects of insecurity and self-consciousness, which makes approaching what few women I meet difficult, if not seemingly impossible at times.

Recently, I’ve met a girl at school, and we get along reasonably well; we share some similar interests, we’re both going into a similar field, and we enjoy each other’s company well enough. There are even some signs that she may be interested in me, since she’s pretty open and friendly with me despite being pretty shy in general, though nothing terribly overt (though things rarely are).

The “catch”, as it were: I just turned 30, and she just turned 20, which isn’t the end of the world or anything, but it does make the situation a bit more complex, particularly because she doesn’t yet know just how old I am. I’m not crazy into her or anything, but part of me also feels that it’s a good opportunity to try and open myself to possibilities I’ve been pathologically avoiding for years, and try to let go and explore taking some more risks.

I do think I need to work on my habitual avoidance of exploring relationships with women, as I generally struggle to even form close or even particularly friendly friendships with women, even (sometimes especially) those I don’t have any intention to date. But something tells me that this maybe isn’t the right time, and that I should back off (as per my usual) and hold out for a more appropriate time. The other part of me suspects that this is just part of perpetuating that habit that keeps potential relationships/friendships at bay, though, and it’s hard to find a way to moderate.

So I’m not sure what to do with my discomfort in this situation. Do I listen to the part of my gut that’s telling me that pursuing this relationship further is inappropriate and I need to keep it cool? Or do I listen to the part that tells me I’m being too risk-averse? And if the latter, how do I go about it while remaining respectful and cognizant of my responsibility as the older (and presumably wiser) party? How do I disclose my age? Should I even worry about it? At what point does it cross over from “it just never came up” to secret-keeping? I know I need to get more comfortable with social risk-taking to make progress in that area of my life, but I’m very unsure about this particular risk.

I want to emphasize that I’m not at all looking to force anything with this particular individual, since I absolutely respect her agency in all of this. But in the event that she’s cool with just being regular old friends with someone 10 years her senior, I’d like to be able to allow that to happen rather than putting up barriers under the pretense of respecting her.

Sincerely,

-Better Sorry Than Safe?

You know, one of the themes I’ve seen crop up time and time again over the course of writing this column is “I respect women! I respect them so much I never talk to them or interact with them unless it’s absolutely necessary!”

Strangely, those same people also ask me why they can’t seem to ever find a date.

I bring it up because a lot of times, people who don’t want to admit the truth – they’re afraid of rejection – will dress it up in more noble-sounding terms. It’s not that they’re afraid of talking to someone unless they have 110% assurance that they’ll succeed, it’s that they’re trying not to make them uncomfortable or that they would never tread where they aren’t wanted or be one of Those Guys that get complained about on social media.

Stop me if any of this sounds familiar, BSTS…

Let’s leave the question of age out of it for a moment – we’ll get back to it, but it’s ultimately a detail, not a cause – and focus on what you’re actually doing, here.

You say that you’re interested in possibly pursuing something with this woman you know, but you have a gut instinct telling you that “maybe this isn’t the right time” or that what you’re doing is inappropriate. Well, funny thing about trusting your gut: first you have to make sure that your gut is actually trustworthy. Yeah, sometimes a gut feeling is your brain picking up on clues and queues that your conscious mind isn’t perceiving… but sometimes what you’re feeling isn’t intuition, it’s just good ol’ fashioned anxiety and you’re back-filling reasons to justify doing nothing.

Just you and me (and everyone reading this), let’s be honest: do you really think this is a genuine “something isn’t right about this” feeling, or is it a continuation of your tendency to avoid taking even the slightest risk? Because I think you already know the answer to this question. You even say it yourself in your letter: you habitually isolate yourself and come up with reasons to steer clear of women you find attractive or trying to connect with them on more than a superficial level.

All of the questions you’re asking as part of “I don’t know how or if to do this” are so banal and so not-actually-a-problem that it’s almost kinda laughable in the obviousness of it. I’m asking this sincerely and without mockery: do you honestly think that you’re so baby-faced or culturally in tune with Gen-Z that your classmate is going to assume that you couldn’t possibly be in your 30s? Or is this just another way of overly complicating an otherwise fairly simple situation so that you can justify not taking action?

I’m not unsympathetic to having anxiety about rejection. It sucks to be rejected; it feels like you’re being judged on every aspect of yourself, even when rejection often has nothing to do with you. But dating and relationships require vulnerability; you can’t have a genuine relationship with another person without opening yourself up to the possibility of being hurt. Trying to avoid making yourself vulnerable to another person just puts barriers between yourself and them. It makes having a true connection impossible because you never actually let them in.

Just as importantly, avoiding the things you’re anxious about doesn’t actually help. All it does is make the fear worse. Now, instead of just avoiding the thing that you’re anxious about, you’re also avoiding the things that might make you feel anxious – you become afraid of feeling afraid. And the more that you try to avoid even the slightest possibility of hitting the tripwire on that feeling, you end up making your world that much smaller and that much more isolated as you begin stacking more anxieties on top of it. You end up creating a situation where just existing in the same room as someone you’re into becomes intolerable.

If you want to actually connect with someone and forge the kind of relationship that might lead to something more than just a nodding acquaintance, then you have to start getting comfortable with risk. You have to get comfortable with the possibility of things not working out. And you have to start being willing to recognize that, while rejection can suck, there’s a vast difference between the momentary discomfort of being rejected and the catastrophic social death you fear would come from saying “hey, I enjoy talking with you. Would you like to grab a coffee at the student union before your next class?”

Now as for this woman specifically, including the age gap… let’s be real here. If it’s as you say, then you’re going through all of this for no real reason. But for argument’s sake, I’m going to keep neutral on whether you’re trying to downplay this, why or whom you’re trying to convince (me or you) and take it at face value. If you’re not that into her as anything other than someone you enjoy hanging out with, then there’s no real reason to not at least hang out on occasion and get to know her on more than a superficial level.

I think part of the problem here – outside of your habitual self-isolation – is that you’re doing a little dickful thinking and that’s causing part of the problem. I’ve seen a lot of dudes crash themselves on the rocks of mistaking friendliness for romantic interest, in no small part because men tend to avoid emotional intimacy and close friendships with anyone besides their romantic partners. As a result, even basic acts of friendship start looking like signs of attraction. So when an attractive woman is being nice or acting like a friend, it gets read as “she wants me!” And to someone who is both cripplingly lonely and prone to anxiety around rejection, you create a situation where now you feel like you both have to avoid this and that you need to pursue this because it’s the most recent (and possibly last) chance for love.

So my suggestion is that you slow your goddamn roll. Drop the assumption that this is anything other than someone being friendly to another person that they share some commonalities with. Stop assuming that you’re a mind-reader or that you are socially skilled enough to see The Matrix and understand all the dynamics in play – especially when you’ve already said you’ve spent decades closed off and avoiding people. Sometimes the path of wisdom starts with understanding that you don’t know things and that’s ok.

Here’s what you do: you work from the place of “she seems nice and we seem to get along” and assume that this is exactly how it appears on the surface until such time as you get concrete evidence that there’s more. And by concrete, I don’t mean reading the tea-leaves, I mean either she says “I like you as more than a friend” or you go out on an actual said-the-word-date date. Let go of your expectations, let go of trying to make this more than what it already is and just work from a place of “well, if we enjoy talking to each other, let’s hang out and talk and get to know each other. Maybe we can be friends!”

And as for the age difference and whether you’re “hiding” things from her? Well, first of all, I promise that you aren’t hiding a goddamn thing. She may not know the exact number, but I can all but guarantee you that she knows you’re older than her. More importantly though, for all that people make a big deal about age gaps and whatnot, she’s a grown ass adult. She’s old enough to vote, work, pay taxes and fight for her country, almost old enough to drink in the US and, importantly, not a child. She’s fully capable of deciding whether she’s interested in a relationship with you or not, and under what terms or conditions. You can respect that someone is younger than you without infantilizing them or condescending to them in the process – including the way people wildly misunderstand the “you’re not done developing until you’re 25” thing and how brain development works.

But worrying about the appropriateness or inappropriateness of the relationship is putting the cart way before the horse. Stop worrying about “is it right to date her” and just focus on not letting your anxieties throw more barriers between you and other people. So stop overcomplicating things. If you like her company and she likes yours, hang out. If not, then don’t.   

Avoidance doesn’t work. Confidence is as much about taking risks and surviving as it is about anything else. And that’s why, at the end of the day, the only way out is through.

Good luck.

Dear Dr. Nerdlove,

I met a man at a cafe whom I noticed since I go to this cafe each weekend and so does he. I observed him and I assumed he would not like me and I stayed away and looked at magazines. But he found a way to be near the door when I was walking out and we talked and he asked if I knew his ex-wife. I do not know him or his ex-wife or anyone he mentioned to me really.

But he asked if he could buy me a coffee so I said yes.

I felt confused but excited that this man might like me! But then I was worried he might not. I felt like I stepped back into “having a man” with him but I haven’t in 10 years and maybe never but for some reason it was nice to feel like I was with him and he was buying me a coffee.

But I decided I wanted to date him but when I decided I needed to leave the cafe, I asked for his phone number so we could meet again and he said no.

Since then, I have been back to the cafe and I saw him there again and he invited me to sit down. I did sit down and he seemed to say the same things in a way. He keeps mentioning his ex-wife. But I thought…ok maybe he needs a friend, someone to chat with at the cafe. So, I sat and tried to talk but I don’t know enough to offer him advice. I am sad that he is sad over his ex-wife and I wish he was ready to move on and date me but maybe he is not that interested in me. I said that to him…that if he met someone that helped him forget his ex then maybe it’d be better that obviously I am not helping him forget and move forward. He said it has been 10 years …geesh.

I am thinking now that I need to avoid him since I want a relationship. Not necessarily with him but since this is my chance getting out of my house to meet a guy, hopefully who wants to be together a lot (relationship) maybe I should not talk to him. I hardly get out anywhere. At first I thought wow seems perfect when we sat and talked the first time so I was very sad / disappointed when he said no, that he does not want to exchange phone numbers.

What do I do?

Moving Forward Using All My Breath

OK, there’re a couple things here that are worth unpacking. First and foremost is that, yeah, it kinda sucks that this guy isn’t really interested in dating and seems to be hung up on his ex-wife. But let’s be honest here: the main reason you are hung up on him is that he’s apparently one of the first men you’ve really talked to in a long while. It’s understandable to be flattered by the attention and excited about the possibilities, but this is just a man. A man that you barely know anything about. While I’m sure he’s a nice enough guy – if not in great emotional shape right now – he’s not your soul mate or the last single man in America. Getting hung up on him is more about what he represents (a cure to your feeling lonely) than who he is. I can guarantee you that there are other guys out there, guys who are attractive and single and, importantly, not so hung up on their exes that they’re asking strangers if they know them.

You’re really over-investing in a guy you hardly know… and a guy who, let’s be real, isn’t exactly demonstrating that he’s worth your investment in the first place. I understand the excitement, believe me. I understand the feeling that this is the first opportunity you’ve had in a long time and you need to snatch it up like a duck on a junebug. But getting that hung up on a stranger is just an invitation to a broken heart, inviting unnecessary but inevitable pain into your life for no reason other than he was there.

The question of whether this guy is interested or not or why he’s still hung up on his wife or how he could move on are ultimately irrelevant. What’s important are two things: 1) he’s not in great shape, emotionally and 2) he’s not interested. That’s all you really need to know, here. And more to the point, the fact that he’s not in great shape should be the sign for you to not make him the focus of your interest. His problems are not something for you to fix. He’s not a project and the last thing you want in a relationship is a fixer-upper – especially when you’re still needing to do some work on yourself.

Do I think you need to avoid him? Not unless you honestly can’t bring yourself to talk to anyone else because you’re holding out hope that he’s going to change his mind. IF that’s the case… yeah, you need to put some distance between you and him so that you’re not wasting your time watering a dead plant.

What you should do is take that feeling of excitement you felt upon meeting him and let that motivate you to get out of the house more and put yourself into fortune’s path. Yeah, this guy isn’t in any shape to date, nor is he into you that way… but that thrill you felt should motivate you to be on the look out for the people who are. As great as it felt meeting this guy and the hint of possibility, meeting someone who’s ready, willing and able to date will feel even better. If you want to find them, you have to go to where they are. And since they’re not in your house, then that means going out into the world and meeting them there.

Let this encounter be the thing that spurs you on. He may not be the love of your life, but he could be the thing that motivates you to go to the place where you ultimately meet the man who is.

Good luck.