Why Do All My Dates End The Same Way?

Estimated reading time: 15 minutes

Hi Dr. NerdLove:

I guess I need help in terms of making sense of a bad run. I’ve had a few first dates over the last 6 months and none of them have really gone the way I’ve wanted them to, some of which I’ve talked to you about. These are all people I’ve met through grad school, and there was a trend with them where I had either met them through class or through a friend, gotten to know them, and asked them out. Often the first dates seemed to go pretty well. The most recent one was someone I had felt was interested and asked out a couple days after our class, and we had played a couple of card and board games at a bar. It seemed like we were both really enjoying ourselves and we were joking around a lot, and by the end of the date we had gotten pizza before leaving, and they became quite touchy after, and gave me their number after the date (we only connected on social media) and we had talked about seeing a movie. However, the day after, after they agreed to the day, they mentioned that they just wanted to be friends and hoped I was cool with it.

I’ve had this happen before; once with a girl I have talked to you about who was 5 years older than me, and another one who essentially everyone warned was using me. As well, they all had a lot of similarities; all of them were older than me, with the current one also being 5 years older than me, being an out of province student who was going back once the masters ended in August. As well, they were all suffering from depression. The current one had mentioned they had been depressed for the last few years, expected to be depressed forever, and that they had been on medication at one point and that they thought they probably should be on medication. The other older one had also disclosed that she was depressed and going through financial issues as well, and had an ex they told me was the only ex they had that really ‘counted’ and they seemed to be in frequent contact with them, although she said it wasn’t romantic. I wrote to you about another one in “Was I right in Cutting Contact with my Crush” and it was essentially the same deal. Now, I often relate to these people because I have struggled with depression in the past. However, right now it’s kind of under control; I’m medicated and I am seeing a therapist. Obviously I have my off days, but for the most part I’m functional.

With all this, I guess there’s a part of me that’s wondering what the issue at play here is. It has felt like I’ve been having a bad run lately, which makes me feel hopeless because I would like to find someone, and I’m wondering if it’s my fault these dates aren’t panning out. I’ve been told I’m quite funny but I have an issue with sometimes stepping on peoples toes verbally I’ve heard. However, I’m also aware that these all had things that would’ve worked against them; all being depressed, the age differences, and being in the nightmare that is grad school probably didn’t speak to these working out, especially because this program is only one year and right now there’s only 5 months left. It’s also making me feel a bit hopeless, or like I’m kinda fucked and that I’m never gonna find someone, whereas other people don’t struggle with dating and can find someone, even when this is only my anxieties speaking. It’s a bit demoralizing, and I’m wondering if you have any advice for both dealing with this, and for maybe screening out partners in the future? I just feel so demoralized after all this; I’ve been single for over a year now, and frankly it would be really nice meeting someone and having it work out.

Thanks,

Bad Run

One of the first things I tell the people I work with who are having long-running recurring issues with dating or relationships is to start looking for commonalties. What sorts of things keep coming up, what do each of those dates have in common, are they all falling apart the same way at approximately the same time and so on.

The benefit to this exercise is two-fold. First, it gets you top start taking a critical eye to your circumstances. Once you start examining those relationships in more depth and looking for patterns, you engage parts of your brain that can help you recognize things that you might not have noticed consciously at the time. When you start really looking for things that seem to happen every time, you often end up identifying issues that you may not have been aware of. Those help point you towards deeper issues that have been lurking beneath the surface; the more obvious problems may be symptoms, rather than causes.

The second is that it helps break the cycle of helplessness; you’re taking actual steps and starting a process of action to try to identify and solve the issue. This reminds you that you’re not, in fact, an entirely powerless pawn in the hands of an uncaring universe. You have agency and are reminding yourself that you can do more than sit there and mope about it.

Fortunately you’ve started the process. And… well, damned if that’s not a surprisingly specific set of commonalities among those women. The age gap and the issues with depression being the biggest commonality is interesting and something being that specific suggests that there’s more to be unearthed here. At the very least, this suggests that there’s something about these women that you respond to but that also is contraindicated to a relationship with you.

As easy as it would be to say “well, it’s simple: date people closer to your age and who aren’t dealing with untreated mental health conditions”, that’s not actually helpful. It’s a little like the George Costanza theory of “listen to whatever my instincts say to do, and then do the opposite” – great for a gag in a sitcom, not so much for real life. That’s still dealing with a surface level issue; you’d be on the lookout for symptoms of something that may well be more fundamental than just “look, I like grad-school goths”.

I suspect it’s worth digging further into this. What, precisely is it about these women who seem to share an age and mental health issues that you vibe with. Does something about their behavior – behavior that may be caused by their depression – appeal to you? Is there something similar to how they act, to their basic outlook or other aspects of them that makes them more appealing?

Now, the tricky part is that you need to look at yourself as much as you look at them. This can be hard, especially when you have your own struggles with depression, because this can easily turn into self-blame. It’s really important that you see this as trying to resolve a problem and make things better, rather than treating it as “it’s all my fault” and using this situation as something to punch yourself in the nuts with. But this sort of recurring situation may well be a sort of “check engine” light for your own growth, development and emotional health.

Is it possible, for example, that their depression means that they’re not putting as much effort into their presentation and so they feel a little less intimidating than someone who’s gotten up and put on a full face and did their hair before going to their program? Could it be that there’s a part of you that recognizes their depression and their struggles and thinks “well, this might mean that they’re more likely to accept me as a potential partner?”

Or is it possible that there’s a hint of White Knight Syndrome going on – since you’re experienced with keeping your depression under control, you feel like you can help them somehow and this will “earn” you a relationship with them? That it would mean that they “need” you in a way a different person might not?

Or, in another direction, is it that you feel a sort of kinship as someone who has struggled with similar issues and that shared experience feels like a sort of maladjusted compatibility? Or that you recognize something of yourself in their struggles?

If that’s the case, then that would be a suggestion to look inward – that perhaps you’re self-sabotaging in a way that would indicate that you don’t feel like you “deserve” a relationship or you’re selecting for relationships that you know aren’t likely to actually work out. This happens a lot with people who struggle with self worth and depression issues; it’s both a self-inflicted punishment (‘how dare you think you’re worthy of someone who actually cares for you?’) and a sort of self-preservation, a perverse way of keeping yourself safe.

The more you puzzle out why you keep going to this particular well, the easier it’ll be to figure out what the underlying issue is and how to resolve it. It’ll also make you more mindful about the people you’re trying to date; recognizing the why of it all makes it easier to effectively filter out people who are wrong for you… especially if it’s that very wrongness that’s drawing you in.

Good luck.

Hello Doctor,

I’m in a weird spot right now. Currently I’m in a healthy and loving relationship and we’ve been together for a year. Recently I’ve been thinking I have feelings for a close friend of mine that I’ve known for 5 years. Throughout those 5 years we’ve had sleepovers, painted nails, have traditions, and have gone on trips and “side quests” together. If you’ve seen new girl we’ve always compared our friendship to Winston and CeCe.

I feel secure in my relationship with my girlfriend and we’re looking for an apartment together right now but I also can’t stop these thoughts and feelings about my friend. I don’t know what to do to resolve this.

Betty Or Veronica?

Long-term readers know some of what I’m about to say, BoV: just having a crush on someone isn’t indicative of anything other than being a mammal with a sex drive. The fact that you find someone else attractive doesn’t mean that there’s anything wrong with you, with your relationship or the state of the world. It means you have eyes and a limbic system and there are things about the person you’re crushing on that appeal to you. Being in love with someone doesn’t mean that you won’t be attracted to anyone else, even when you’re still neck deep in the New Relationship Energy stage. This is something that happens incredibly frequently, to a wide range of people. While the realization may be shocking or distressing, it’s really commonplace and just a reminder that loving someone doesn’t mean that they’re the only person in the world you could be attracted to. You’re not betraying your relationship by having thoughts or feelings.

Nor, for that matter, does having an attraction to someone mean that you need to act on that attraction. A boner isn’t a direct order from your commanding officer, after all. You’re a ghost driving a mech suit made out of meat and chemicals; getting the hots for another person is just meat responding to meat. You’re the one who ultimately decides what that meat suit does. Don’t want to break up with your girlfriend to pursue that crush? Ok cool… so don’t.

But honestly, I’m increasingly of the opinion that a lot of this comes down to folks not really understanding love. Part of it – current popularity of the Polyamory Discourse aside – is that people don’t understand that love isn’t a zero-sum game. Loving someone doesn’t mean that you have no love to give someone else. Loving one person and realizing you may have feelings for another person doesn’t take away from either of them. You can certainly be attracted to more than one person at a time, to be in love with more than one person at a time, and not actually take anything away from any of them. Loving more than one person doesn’t make the love of them less “special” or “meaningful”; it just means that you have a lot of love to give.

Similarly, there’s nothing weird or unusual about thinking that you, specifically, have feelings for your best friend. Of course love them. You’re incredibly close, you clearly have emotional compatibility, you share intimacies and experiences. You have lots of history, you’ve bonded over all sorts of activities and stories. It would be weird if you didn’t love them.

Now someone call 1-900-Mix-A-Lot because here comes a big ol’ BUT.

BUT. That doesn’t necessarily mean that you love them romantically. Yes, it’s possible to love more than one person, but there’re also many kinds of love. The ancient Greeks famously categorized love in many different forms: eros, the love of the body or sexual attraction; philia, the love of close friends; storge, the love of family; agape, the sort of unconditional love that we equate with gods and religion.

So yes, you absolutely have feelings for your best friend. The question is “what kind of love are you feeling?” And this is a critical question to ask because, quite frankly, straight cis guys tend to be really bad about understanding the difference.

I’m sure you’ve seen all the talk about the loneliness epidemic and the number of men who have few close friends (or any friends at all). Part of the reason for this is entirely social; men, specifically are socialized to equate emotional intimacy with romantic and sexual intimacy. From toddlerhood to puberty, boys tend to be gloriously open-hearted; we love and adore our friends and think nothing of it. But almost from the moment we hit puberty, we’re bombarded with lessons that teach us that the sort of open-hearted, freely expressive sort of affection we have for our friends – especially our male friends – is bad and wrong and signs of weakness or “being girly”… or worse. Even in the far flung future of 2024, we’re still taught that the casual affection, expressiveness and ease of physical contact is bad, especially between boys (lest anyone think you’re *gasp, shock* a homosexual) and is ultimately reserved for someone you are going to sleep with. And so a significant outlet for emotional intimacy and physical contact is cut off, stigmatized and otherwise rendered taboo.

But of course, the need for that intimacy and contact – touch starvation is a very real thing – doesn’t go away. So you have generations of boys growing up with needs that they’re not even supposed to acknowledge they have, let alone being given the tools to address and fill them.

Women, on the other hand, don’t receive those same lessons. This is why female friendships often seem weird to straight men; our same-sex friendships are activity-based, using outside activity as pretext for bonding. For women, the bonding is the point; the intimacy, sharing and contact is all part and parcel of it, without the need of an excuse to make it acceptable.

So when straight cis men become close friends with women… it feels entirely different than a lot of male friendships. It’s frequently more expressive, more emotionally intimate in ways that we have been taught to associate almost exclusively with romantic love… or at least with the possibility of sex, in any case.

So it’s entirely possible that part of why you’re suddenly realizing you have ‘feelings’ for your friend is because now you’re in a romantic relationship and some part of your brain went “hang on… this feels a lot like when I’m with my buddy. What the fuck, yo?” And now you’re guilting yourself like crazy over a supposed “betrayal” when in reality, you’re realizing that you were filling a need that you weren’t even aware you had in ways that you were taught were the province of romantic or sexual relationships.

Or, y’know. It could be that you just have a crush on your bestie.

So what do you do about it? Well – assuming that you don’t think you’re polyamorous and don’t want to first negotiate an open relationship with your girlfriend –  you do… nothing. Literally nothing. As in, don’t try to not think about it, don’t try to force those feelings away, don’t do anything proactive about it at all. Just notice those feelings when you experience them, name them (“oh, that’s my crush on CeCe”) and redirect your attention to whatever you were doing before you realized you were having a feeling.

Seriously, that’s all that needs to happen. Crushes are like fire; if you feed them, they grow. If you don’t give them fuel, they die out. You don’t need to hash it out with your friend, you don’t need to make a tearful confession to your girlfriend. You can just let it be. They only become problems when people treat them like problems instead of things that just happen and have no deeper meaning than just having them.

And as I said: even if it is romantic, you don’t have to do anything about it. Loving your best friend doesn’t take away from your love for your girlfriend. It’s not good, nor bad. It just is. If you don’t want to pursue something with your BFF, then don’t. You don’t have to do anything about it. Feeling a feeling isn’t an edict from the gods. It’s just a feeling. You and you alone decide what to do about it. And if you decide to do nothing, then do nothing. Just let it be.

Now all that having been said, let me make one caveat: not doing anything besides just acknowledging that you feel the feeling means just that. Don’t behave differently with her – you don’t need to pull away, but you also don’t want to start flirting or acting more romantic with her either. You’re a grown-ass adult; you should have enough self-control to not start pushing the line with your best friend by starting to take things in a flirty direction just because you’re feeling a feel.

Functionally, this means that if you’re not going to pursue things with your best friend, you also don’t start playing weird games of chicken with yourself. I’ve seen a lot of guys in monogamous relationships develop crushes or attractions on people who start “accidentally” putting themselves in temptation’s way, setting things up so that things “just happen” and oops they tripped and now their dick is in someone else.

If you’re monogamous or made a monogamous commitment to your girlfriend, that doesn’t mean that you don’t need to start avoiding your friend or not taking trips together or any of the other things you were doing before you started feeling your feels. What it does mean is that you need to have enough self-control to know where the line is and to stop yourself from even tip-toeing up to it – the same as you had been before now. Otherwise, the issue isn’t that you had feels for your friend-who’s-a-girl, it’s that you played stupid games with your boner and you’ll win stupid prizes as a result.

In all seriousness, it sounds like things between you and your bud have been fine until now. There’s really no reason for that to change; you’re just more aware of your emotions than you were before. That’s all.

Good luck.