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Woe Is Me! “Why Do Men I Meet Never Want to Date Me?”

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Aug 30, 2020

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Image credit: Pyaasa (1957)

Woe Is Me! is a series in which The Swaddle team indulges your pity party with advice you’ll probably ignore.


This happens to me all the time. I meet men, I connect with them and then they just don’t want to date me. I’m tired of this cycle. I don’t know if men are the problem or is it me?   

— Girl, Solo

AS: I think dating is so much about the right time and right place – not geographically, just about where someone is in their life in terms of emotional and mental availability. And if these variables don’t align for two people, it doesn’t mean there’s anything wrong with either of them. It’s possible that whoever or whatever you’re approaching, you’ll do it with this tired, frustrated state of mind. You probably feel done with dating, and I totally get that. Maybe just take a break for a bit, and focus on yourself?

Again, not because there’s anything wrong with you, but because in all the ups-and-downs of dating life, the most important thing that you need to protect is your own happiness and sense of self. I know this is clichéd — and I probably sound like I’m channeling that sadhu-healer talking to Julia Roberts in ‘Eat Pray Love’ — but, I think if you just put yourself first, always value yourself, and come back with a positive, refreshed approach, stuff will fall into place – eventually.

KB: Guess what? The vast majority of the people who meet and connect don’t end up in long-term relationships. Did I just blow your mind? But seriously, this is a numbers game. You can’t possibly think that you want to seriously date every single person you meet, nor should you expect that every person you meet wants to date you.

One of the best lessons I learned as a young adult was that not everyone will want you, and that’s totally OK. Internalize it! Shout it from the rooftops. Rejection is totally fine. It doesn’t mean anything about your value as a life partner, or you as a person, or anything else about how lovable or funny or smart you are. It just means that person didn’t want to date you. See how innocuous that is? Now get over it! And keep dating. One day, maybe you’ll find someone who really excites you, and you’ll excite them back. And then you’ll be done with the cycle. Until then, enjoy the process of meeting new people, fine-tuning your needs and wants in a partner, and handling rejection like a person who really knows what they want.

DR: Your woe has hit the ‘hard relate’ button on my psyche — so much so, that it feels like the 2018-me wrote this. I understand that the cycle would make you want to doubt yourself, it’s only natural. And, while it’s never a bad idea to introspect, upon a prima facie reading of your woe, I don’t think it’s your fault that these men you’ve been meeting don’t seem inclined to stick around. And, I really hope you don’t go down a downward spiral thinking you’re not “worthy.” But, one thing that I would definitely ask you to think about is if you’re choosing a series of emotionally unavailable, pretentious pricks — that could explain the pattern you’ve mentioned. There are way too many of these men on dating apps, and out there in the world too. So, just statistically, I know you’re bound to swipe right on them, at some point. If you’re not looking for anything deep, I think these creatures would do just fine, but if you are, then I would suggest that you be a little more conscious of the kind of men you’re investing your time and energy in. Use your judgement. If a man seems like he’s the flaky, “fuckboy,” “fake woke dudebro” variety, nothing that you do is going to magically change them overnight.

Alternatively, you can take a break from actively pursuing a relationship for a while, and take a breather from toxic men. Letting things take their natural course while you sit back, relax, and introspect on your choices, while pursuing other interests that bring you joy, and help you learn more about yourself as a person, can be fun too. I wish you luck on your future endeavors! But, before I conclude, I just want to quote Cher: “A man is not a necessity,” and, “It’s nice to have, but you don’t need it to live.”  

RD: Hmmm, it could be both. Definitely check for red flags within your own behavior, much like you’d do for dudes you come into contact with. Ask your friends for help. But it could also be the kinds of dudes you choose? I’m thinking of that movie trope in which women choose men who are not available as some kind of sadistic emotional safety thing — is that what’s going on with you? 

But at the end of the day, I will say that finding a person who wants the same things you want is very, very, very difficult. It might seem like everyone around you is getting coupled up and things are working out for them, but trust me it’s merely an illusion. Probability wise, it’s rare. So take breaks from dating to accommodate your mental health, and keep at it if and whenever you want. And if things keep going to shit, try another age-old movie trope, if not for answers, then some entertainment — call up all your exes, and do the relationship autopsy. Why didn’t they want to take things further with you? It’ll be brutal, but it always works for people in the movies. 

ADT: This whole “am I the problem or do all men suck?” thing is your hurt ego speaking. What really helps me not wallow when I’m rejected is that rejection is purely ego-based. When you overcome the shock and hurt your ego suffers, you know that the person who rejected you doesn’t fit into your life anyway. I’d suggest trying to push away the hurt and looking at your past dates super clinically. You know they all kind of sucked, don’t you. Analyse why and then proceed. When you meet and connect with men, do you make it clear that you want to date them? Secondly, do you have a very particular type of men that you pursue? Communicating very clearly that you’re here to date is a way to stop wasting your time on connecting with men who want to be friends. Plus, not having a particular type also helps, because with a type, you’re shutting out about thousands of men who could be super into you!

LG: That’s a tough ride, my friend, I’m sorry! I’m afraid there are too many unknowns in this equation to offer specific advice, but as much as it’s nice to be part of a twosome, can I suggest stepping out of the cycle and having some you time? Focus on yourself, pamper yourself, become your biggest cheerleader and coolest, most capable friend. Hang out with other platonic buddies who fill these roles for you too, and revel in platonic intimacy for a while. The dating often clicks right when we’re looking for it least. And even if it doesn’t, you’ll have strengthened your existing, loving relationships and invested love in yourself, which is always worthwhile.

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Written By The Swaddle Team

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