Advice on All your Love Life Woes

Welcome back to another edition of Dear Dating Bitchthe modern, slightly crass, version of Miss Manners.

But, first – If you missed any of the last few advice columns, you can catch up on them here:

Dear Dating Bitch: Breakup Edition

Dear Dating Bitch: Anxious About Appearance

Dear Dating Bitch: Modified No Contact

And now, let’s get to the advice, shall we?

(*Note: questions may have been edited for length/clarity)

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Q: I’m the only single person within my circle of friends. I get really anxious using dating apps and have low self-esteem compared to my outgoing sister who finds meeting people easy. Can you help push me in the right direction?

– Love, The Shy Sister

Dear Shy Sister:

I can imagine how frustrating – not to mention isolating – it must feel to be the only single girl in your friend-group. If you haven’t already, I would suggest that you first mention your feelings to your friends. Not to evoke a sense of pity from them or make them feel guilty for their own happy relationships, but rather so that you feel just a tiny bit less alone.

If your get-togethers are always comprised of both parties of these couples, then expressing your feelings might also help ensure that the occasional girls-only event is planned. (And perhaps your friends know of some suitable suitors to set you up with, too!)

Next, I can’t help but notice that your letter conveys a deep sense of insecurity. You mention that you have low self-esteem and then you follow it up with a self-deprecating comparison to your sister. While it may be true that your sister is more outgoing than you, that doesn’t mean that she doesn’t struggle with anxiety or confidence issues.

I say that because I think sometimes it can be a reflex to assume that people who have traits we lack (or, feel we lack) have it easier. But doing that isn’t helpful because it puts us in a victim-mentality.

For instance, there are times when I see an incredibly beautiful woman (like, super-model beautiful) and instinctively think “If I looked like that, I’d be so much happier/more confident.” And, sure, for the sake of argument, if I did look like that, I might actually be happier or more confident.

But, by putting the onus of my happiness and confidence on something that is fundamentally outside of my control, I put myself in a position of helplessness. I can’t very well make myself look like a supermodel, so does that mean I can’t improve my confidence? Of course not!

You may not be able to control how outgoing you are, or the fact that you have a harder time meeting new people, but that doesn’t mean that you can’t work on improving yourself.

Have a question of your own you’d like me to answer? Send it in using my easy online form!

So Work on Your Confidence, Sister!

You don’t say exactly what it is that you’re self-conscious about, but I think the most important thing you should focus on improving at this point is your own confidence.

Easier said than done, right?

Unfortunately, yes. But you can start by stop comparing yourself with others – including your sister! It’s not a competition of who’s more outgoing, so instead of treating it as such, try and re-frame it in your mind as a non-judgemental statement.

Rather than thinking, “My sister’s more outgoing than me (and, therefore better at meeting new people)”, try thinking, “My sister is an extrovert – period.” No comparison or judgement is necessary!

Stop Comparing Yourself to Improve Your Confidence.

As simple as that might sound, by re-framing the way you think about certain qualities, you’ll also re-frame the way you feel. Being extroverted isn’t good or bad, therefore neither is being introverted.

There are, of course, numerous ways to try and work on your self-esteem (I would suggest practicing daily, self-love affirmations), but I’d like to move on to the next part of your question: being anxious about using dating apps.

I’m assuming, based on the rest of your letter, that your dating anxiety stems from your low self-esteem. It’s understandable that if you’re feeling insecure about the idea of getting out there in the dating pool – after all, dating is an inherently vulnerable activity – but it doesn’t have to be so stressful!

I think that you might be putting a lot of pressure on yourself – you feel like you’re the only singleton left of all your friends, you want to find a partner, you have a lack of self-confidence – with all of that combined, its no wonder you feel so anxious!

So, for now – don’t go into these dates with the expectation (or even DESIRE) for a relationship. Go into them for the sole purpose of improving your comfort level.

Continue to go out on dates, but look at them as practice. You’re practicing your social skills, your flirting, your ability to meet new people. By doing that, you’ll improve your confidence and that in itself will go a long way to helping you change your relationship status.

Good luck!

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That’s it for this week everyone! If you have questions about your love life, you can email me at OR send me your letter anonymously using this form.

As always, let me know your thoughts in the comments below and share this article with anyone who might need to hear it.


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Advice about improving confidence in dating life


  1. avatar

    This was so helpful! I think as you said sharing with your friends how you feel can help both parties understand more of the situation, not for sympathy but just to be on the same page. Also not comparing yourself to others is really the best advice x

    1. avatar

      Yes, absolutely. Sometimes other people don’t realize how their words or actions effect us, so letting them know is a good idea.

  2. avatar
    Brianna Stryker says:

    This is crucial advice! Being the only single one in a group must be tough, yet your friends are your friends for a reason so you should be able to confide in them- like you said, not for sympathy or anything, but to feel less alone. I love the idea of going on dates without the expectation of them forming relationships. You are right, expecting that does add a ton of pressure and when you already feel pressure from your friend group simply because they have partners and you do not, that is a lot to deal with. Practicing will help increase your confidence and you need to work on improving that in order to be happy. I love this post! Thanks for sharing. I am sure it helped the person who needed advice.

    1. avatar

      Thank you!

      That specific piece of advice I gave is something I actually did after my last breakup. Going back out into the dating scene was really overwhelming at first, so I decided to look at every date as practice. And, in part, as a way to build confidence. I figured, if I don’t expect anything from this, it won’t feel as overwhelming or scary.

      I’m so glad you thought that was a good piece of advice too! I know some people think it’s wrong, that it’s “using” others in a way, but I think when you’re in a bad place – either due to anxiety or heartbreak, it’s OK to put yourself first.

  3. avatar
    Grace Amadi says:

    This is really nice… “stop comparing yourself with others” won’t forget that. Thanks for sharing

    1. avatar

      Thanks so much for reading!

  4. avatar

    Nice post Katie! It has a great message inside. Though the question was related to relationship but I can relate it to many of the people around who are comparing themselves with others and by doing this indirectly they are loosing or demeaning their self-esteem and confidence. Which I think is very much required to stand into this world, otherwise nobody will come to know that you’re lost. I truly liked the way you’ve encouraged the shy sister. This is truly a amazing post!

    1. avatar

      Thank you so much! I hope the writer of the question finds it helpful as well.

  5. avatar

    Nice post! Confidence is key in everything!

    1. avatar

      It really is!

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30ish Lifestyle blogger, relationship "expert," and modern-day agony aunt.
Sometimes humorous, always honest.