Dating and Relationship Advice

Dear iris,

I’ve been single for the past three years, and it’s starting to get to me. I’ve had a few “almost” relationships, but each time the guy has shown some sort of red flag (like saying he’s not over his ex, or he’s too busy to date me). I’ve walked away from all of those relationships, but since it’s been three years and I still haven’t found what I’m looking for, I can’t help but feel regretful for leaving people I could have potentially tried harder with. How can I stop feeling regret? Should I have stayed with them and tried to work things out?

Should I reach out to them to try again?

Signed, Tired of Being Single

Dear, Tired of Being Single

I appreciate your honesty and vulnerability in asking this question. It’s not easy to admit you’re not happy with your dating life and that you want more. That alone is a big step and something to feel proud of.

So you want more out of your love life, and since it’s been three years, you’re wondering if you made mistakes in letting go of some of the people you dated. You went as far as to say you regret your decisions at times and are wondering if you should reach out again. Let’s focus on that last bit first.

Walking away from someone you’re dating who can’t meet your needs is an INCREDIBLE skill that most people lack. It tells me you have firm boundaries. Nothing you mentioned (not over their ex, being too busy at work) seems like something you should’ve "worked through." Those are legitimate reasons to move on.

If you’re still concerned about how you push people away, explore your feelings around intimacy. What if someone wanted to be close with you? Would you push them away or feel comfortable? Same with vulnerability: does the word make you want to run and hide under your covers?

From what you described, it doesn’t sound like what you’re struggling with is a fear of intimacy. But if you think you might, do a bit of research about attachment styles. You might have an avoidant attachment style (don't worry, it's not a death sentence). Learning how to feel more comfortable with intimacy could do wonders for your love life.

Circling back to your question: do I think you should reach out again? Not really. The only exception I’d make is if you dated an emotionally healthy person whose healthiness you weren't ready for. Instead, focus on moving forward, not backward.

A good way to do that is to reflect on the qualities you looked for in the people you wanted to date. What made you want to go on a date with someone initially? Was it their height, hair color, cute smile? Maybe that they had the same hobbies or interests as you? Perhaps it came down to something as simple as a funny line in their dating profile.

Or was it deeper qualities like humility, patience, kindness, and emotional maturity? While those things might not sound sexy, they’re green flags to be looking for on dates. Focus on them rather than the elusive "spark" so many people talk about.

I know that loneliness is a strong emotion. It can make many people forget their boundaries and take any sort of love that’s handed to them. While I want you to find that great relationship, I also don’t want you to accept less than you deserve.

Become clear on whether you struggle with intimacy. Make sure you’re saying yes to the right kind of people and even giving those a chance who you usually wouldn’t have (you may just be surprised). And know that you’re heading in the right direction, even if it may not feel like it sometimes. A great relationship isn’t something you can force.