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Kathy’s Window: Why I find it hard to date

Dating in midlife is hard enough, but it's even more challenging when you have an anxious attachment style.

An over-50 Generation Xer sees life through a new lens: Kathy’s Window is where Kathy shares her thoughts on the world through a new lens. From growing up in the 70s and 80s to having three Generation-Z kids, and going through certain experiences in her life, she now sees the world in a different way. Ideas that were considered the norm in the 70s, 80s and 90s are now no longer socially relevant or acceptable. Kathy explores the new ideas through the lens of someone who has been on both sides of the ‘glass’.

DATING in midlife is hard. There are so many reasons why. But it’s particularly hard for someone who has an anxious attachment style like me.

What is an anxious attachment style? When someone has an anxious attachment style, they are anxious when they develop an attachment to someone. They can become insecure, confused, possibly jealous or untrusting, or they can struggle to open up fully to someone. Someone who has an anxious attachment style may not struggle with all of these problems but will at least have a few. It also manifests in a feeling of unworthiness of being loved and going above and beyond to earn the love of those around you – being extra loving and serving and foregoing your own needs for the sake of the other. The feelings of unworthiness can be mostly subconscious which is definitely something I’ve struggled with as I’ve done a lot of work on self-love. I’ve even written two books on the topic. The thing is, you can work on loving yourself and even feel that love, but accepting behaviours from a partner that are not healthy and nurturing shows that the sense of worthiness hasn’t permeated you deeply enough yet.

Also read: Brains in Pain: Strategies to self-regulate

Another thing that an anxious attachment style creates in me is an intense desire for intimacy/closeness and a relationship. My longing for a relationship is quite strong, and I struggle to feel totally happy until I’m in one, which is also not healthy. It also makes me project my ideals onto a person before I even know them.

When you go on a dating site, you are presented with a ‘cover’ of what a person really is. First of all, you have what they look like presented by a few photos, which don’t show the nuances of a person’s gestures, expressions and vibe. Then, you have a few words that they put in a profile to describe themselves. It’s easy for me to fixate on some things that they’ve put on their profile. For example, one man put that he’s gentle and kind. Well, that’s a winner for me, but we didn’t match as he didn’t like me back. I was frustrated with that and didn’t want anyone else. But, what if several other men are also gentle and kind, but they didn’t put it on their profile for some reason? I could be missing out. When it comes to dating, I tend to want to rush straight to a ‘committed long-term relationship’, but it takes time to get to know someone. With dating sites, even longer. (Sadly, sometimes dating sites are the only way to meet someone at a certain time in your life.)

Why is it so hard on dating sites?

For one, you have to first get their initial like in order to match. (I prefer Hinge and Bumble as they allow you to chat for free, but with both of them, you can’t chat until you’ve both liked each other.) Once you’ve managed to find someone who likes you back, you need to get a decent response in the chat. Once that happens, you now have to get a conversation going. Do you know how hard that is with middle-aged men? Either they’re really busy or they’re awful at texting.

Also read: Kathy’s Window: Get rid of the stigma

Once that happens, you have to get to a point where you both want to meet and actually both have time and the desire to meet somewhere – it’s best if you don’t live too far away from each other. Then, you have to go on the date, and whoa, things can change radically when you actually meet the person. The dynamic can alter or flip 360 degrees. How a person is in text can be vastly different to how they are in person. And well, anxious attachment equals possibly romanticising who they are based on certain things they said in their profile or their texts. I was once so enamoured by a guy because he used to send me flirty, cute voice messages and had a really sexy voice. But, he ended up ghosting me because I didn’t want to drive out to his area in the late afternoon and visit him at his house – only on the second date! A couple of other guys I chatted to on WhatsApp had a vibe I didn’t gel with once I actually met them in person. Another person whose sense of humour, intelligence and wit drew me wasn’t monogamous which is a game-changer for me. The thing is I knew that but I kept hoping they would change for me – another classic sign of anxious attachment style – staying in an unhealthy relationship (for you) because you hate being alone.

Other signs of anxious attachment style are an inability to be alone, feeling dependent on others, codependency and a constant need for validation. You have to learn to enjoy your own company – it needs to nurture and feed you. You can’t be dependent on having someone in your life for you to be emotionally secure. I think nearly seven years of being single has helped me – now I thrive on alone time – and things like self-love, meditation, my spiritual practice, finding assistance for my mental health, etc, have helped.

One of the biggies that I have to work on is a sensitivity to changes in how a person speaks or behaves and then bending over backwards to make sure they’re okay or the relationship is okay. This applies to all relationships, not just romantic relationships. It can come across that you’re a super nice person who is always kind and helpful to others. Yes, some of it comes from genuine compassion and a desire to help others, but it can also be rooted in hypervigilance developed from trauma in childhood. This brings us to the reasons why a person may exhibit an anxious attachment style.

Most of the time it is caused by childhood trauma or loss. For me, one of the main things was losing my mother at a young age. It can also be caused by inconsistent caring from a primary caregiver, eg, if the caregiver is nurturing at times but then distant, angry or stressed at other times. It can be compounded by someone who has a naturally more anxious personality type. Other causes are abuse or abandonment from caregivers or even trauma/loss/abuse from previous romantic relationships.

Also read: Kathy’s Window: 5 reasons why it’s harmful to hit your kid to discipline them

When you have an anxious attachment style, you can actually make relationships more tricky and conflict-filled. For example, you lack trust in your partner and check their phone or computer to make sure they’re not cheating, thereby breaching their privacy. Or you want to know if they’re still in love with you or attracted to you – by asking them continually, they feel unappreciated if they are deeply engaged in the relationship. If you have a complex attachment style, which includes avoidant and anxious, you could close off from your partner and struggle to be open and intimate with them at times or obsessively doubt the relationship.

It’s not a hopeless matter

An anxious attachment style is not a death knoll on your chance to find love. There are ways to learn to have a more secure attachment style. If you can find a partner who is secure themselves, it will definitely help you to heal and become more secure yourself. But you don’t want to put all the pressure on your partner to heal you completely and therefore make the relationship shaky. Rather, don’t we want to work on ourselves as much as we can as, in the end, it will help us become happier, more secure, and well-rounded individuals overall?

Also read: How I learned to improve my well-being from within

Therapy would definitely help if you have an anxious attachment style. Also, becoming aware of when you idealise and project your ideals on a flawed human being and choosing to be open to seeing the whole person, warts and all. Then deciding if you’re happy to accept the warts as well as their glowing good points.

When you feel vulnerable, seek validation from yourself. An effective way I’ve done this is by listening to a guided meditation on self-love or practising Reiki. Inner child work is great, too. You do what works for you.

Boundaries – these are so important. It’s one of the biggest lessons I’ve learned in dating. As soon as someone doesn’t respect your boundaries, as nice, attractive or sexy as they are, you have to move on! But most importantly, you need to voice your boundaries as tough as it is, especially when you really like the person and don’t want to lose them. It has taken me years to discover what my boundaries actually are by each time learning about a new boundary that’s important to me. Hopefully, one day, I will no longer have to learn another boundary I need to enforce and move on because they don’t respect it.

Also read: Kathy’s Window: Following my instincts as a parent

The biggest thing for me at the moment is learning to not give and give and give and not receive. For those with anxious attachment styles, we want to be liked and needed, so we will bend over backwards to help and give to a person even at the expense of our own well-being and our own needs being met. If someone doesn’t meet your basic relationship needs, they’re not for you. Yes, no one is capable of doing that all the time, but there must be a general feeling of being seen and heard.

Here’s to all those who are struggling with dating – you deserve the best. Don’t give up on trying. (I’m speaking to myself here.)

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