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Dear Fenella: "I’m a guy in my mid-20s and I've never been on a date"

Dear Fenella:

Sunday 04 September 2022

Dear Fenella: "I’m a guy in my mid-20s and I've never been on a date"

Sunday 04 September 2022

"I’ve got a good job, I’m independent and I really like who I am. The thing is... I’m super shy when it comes to approaching women."

This month, Jersey's favourite socialite-turned-Agony Aunt talks getting ahead in the dating game, sleaze free, with 'Cringing at Castle Quay'...

Dear Fenella,

I don’t know where else to turn. I’m a guy in my mid-twenties and I have never had a girlfriend or been on a date. Whilst I know that sounds a bit like a red flag, I’ve spent a long time working on myself and I now think I have a lot to offer a partner. I’ve got a good job, I’m independent and I really like who I am. The thing is... I’m super shy when it comes to approaching women.

 I see guys harassing and coming onto women all the time thinking they’re being ‘confident’ but really, they’re just being gross and weird. How can I start to feel a bit more self-assured, without being arrogant like them? I want to put myself out there, but not in a way that makes me or anyone else feel uncomfortable.

 Help me Fenella!

 Cringing at Castle Quay

Hi babes,

Awwww, your letter legit made me feel things! I’ve not wept like that since yesterday when I watched a Sandra Bullock rom com, where a loveable rogue melts her character’s cold exterior and she finally learns to be vulnerable again. *Sigh* Sandra is a woman after my own heart...

Can I first of all congratulate you? Not only is your letter sweet and considerate, it demonstrates a lot of empathy and compassion for the women you’re thinking about approaching. I mean if I had a British pound for every time I getcatcalled walking down the street – I’d be filthy stinking rich! Oh wait... I am filthy stinking rich!

What I’m trying to say is that whilst it can be flattering to have a stranger come up to you and express their interest in you, it can also be awkward – especially if they don’t listen to you when you say you’re not interested. And lots of these guys who, as you describe, think they’re being confident and charming, are in actual fact not at all in tune with what us ladies are thinking or feeling.

So, I have good news and bad news for you, Cringey. My very good friend Kourtney Kardashian always tells me to give the good news first then the bad, because it’s humbling.

The good news is that (based on your letter) you seem totes adorbs! Like I’m getting vibes that you’re a genuinely lovely guy who is sensitive and sweet – basically, exactly the kind of guy who is capable of melting Sandra Bullock’s character’s cold exterior and showing her how to be vulnerable again. Let me guess... you’re a Pisces (write me back if I guessed right!)

The bad news is that no woman will ever discover that about you if you never talk to her or show her who you are. But don’t worry, I have a little extra good news for you: Auntie Fenella is here to help! When dating, everyone tries to put their best self forward. The idea is to lure the other person in with your best self, wait until they develop feelings for you and then ambush them with all of your flaws, so they are trapped.

My best self involves extending some hair (my golden tresses and my eyelashes) and absolutely eradicating every other hair on my body. I also only wear sparkly lip gloss for the first six months of any relationship (not as intimidating as lipstick, but still enticing), and I switch my perfume up every single date to keep them on their toes. Works like a charm.

But I think for you (a classic Pisces), authenticity is very important and so you’ve got to make sure you’re giving a good impression whilst still being true to who you are.

Here are my hot tips for you:

  • Don’t look to approach anyone in a bar or a club. It doesn’t sound like your scene, and you could easily be mistaken for your regular common or garden sleazeball. Try somewhere a little more low-key like a coffee shop or a library
  • Start striking up conversations with people you don’t necessarily want to date. If you’re painfully shy, the idea of talking to a stranger is probably a major challenge for you. Practice chatting to your neighbours, the person who makes your morning coffee or your colleagues before you try approaching a woman you like
  • At the end of the day, the worst thing that will happen is she’ll say she’s not interested. Nothing bad will happen to you if you get rejected, your pride will just be a little bruised. You’ve got nothing to lose – so just go for it!
  • Don’t put too much pressure on yourself. Remember what you’ve said in your letter: you’ve spent time working on yourself, you like who you are, and you think you have a lot to offer. None of that will change if you can’t get a date straight away. Take your time and enjoy getting to know people.

Honestly babes, I don’t think you need to worry your sweet, empathetic head. I’m sure once you connect with someone, they’re going to snap you up straight away because you sound like an absolute catch. You’ll find someone soon enough, and even if you don’t, it sounds like you’ve got some great company in yourself already.

Peace and love,

Auntie Fenella xxx


"He told me he loves me but doesn't want a relationship"

"I'm fully obsessed with stalking people's profiles"

"Should I shoot my shot?"

"Make me over, please!"

"I feel like a charity case around my rich friends, but I don't want to miss out!"

"How do I start my self-care journey?"

"It used to be equal... now we’re married, he leaves everything to me"

"Help me make her proposal dreams come true"

"I feel like they’ve all moved on without me"

 "I'm worried that no one takes me seriously"

All of these Agony Aunt columns first featured in Connect Magazine, and you can browse all previous editions for free here.

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