• Apr 15, 2025

#24: 13 Things You Shouldn’t Feel Guilty About in Dating

  • Pink Positive Dating

Ever look back on your dating life and feel... ugh? 😩 Maybe you dated someone who wasn’t a great fit, stayed in a situationship longer than you’re proud of, or feel like your love life should be further along by now. If you've been carrying guilt, shame, or regret around your dating journey—it’s time to let that go. ✨

1. Being Single at Any Stage of Life

Whether you imagined having a partner or a family by now, it's important to acknowledge that your feelings are valid. Society may impose timelines, especially on women, due to biological considerations, but it's crucial to be at peace with your current reality and make progress toward what truly matters to you.

2. Past Dating Choices

Reflecting on past relationships and recognizing that certain partners weren't suitable is a triumph, not a failure. Understanding patterns in past partners allows you to steer clear of similar situations in the future, transforming these experiences into valuable lessons.

3. Prioritizing Your Search for a Partner

Making your partnership search a priority doesn't mean you're desperate. All desires—even those lacking a clear path, like seeking a romantic partnership—deserve attention. Pursue what truly matters to you without guilt.

4. The Number of People You've Dated

Whether you've dated a few or many, these experiences are not a reflection of your worth. They are opportunities to learn about what you want—and don't want—in a partner.

5. Relationships Not Working Out

Breakups aren't setbacks but setups for better opportunities. Be proud of exploring new connections that align with your long-term goals.

6. Taking a Break from Dating

Taking time for yourself when needed—be it for mental health, family, or exhaustion—is vital and healthy. Think of it as re-centering yourself to find a partner who truly matches you.

7. Thinking of Marriage on the First Date

Dating with intentionality is crucial. Knowing whether you share long-term goals, such as marriage, can prevent wasted time and align you with a more suitable partner.

8. Deciding Against Someone Good on Paper

Chemistry is just as important as someone meeting your checklist. Trust your feelings, and don't be afraid to move on if the connection isn't right, even if they seem perfect on paper.

9. Expressing Your Needs and Boundaries

Open communication about your relationship expectations is key. Ensure your needs and boundaries are respected to find a partner who genuinely aligns with you.

10. Using Dating Apps and Singles Mixers

Attending singles events or using dating apps is not a sign of desperation but a proactive approach to finding love on your terms.

11. Being the Pursuer as a Woman

Making the first move can empower you to find a partner who's a good fit. It's about actively choosing who you want to be with.

12. Asking for Reassurance and Clarity

Clarity in relationships avoids confusion. It’s essential to discuss where a relationship is headed to ensure compatible dating goals.

13. Realizing You're Out of Someone's League

Recognizing your growth and refusing to lower your standards is an important part of your dating journey. Aim for relationships where both partners see each other as equally valuable.


Big Pink Question

Every episode ends with a Big Pink Question, a powerful reflection prompt to help you practically apply sentiments from today’s episode directly into your dating and relationship life in a transformative way. This episode's Big Pink Question is:

What have you carried—guilt, shame, or other emotional baggage—around in your dating journey? How will you implement some of the mindset shifts from today’s episode to reframe certain aspects of your dating life into something that ultimately enables you to elevate toward your dating goals?

Take some time to reflect or journal on this prompt. You never know what a good reflection will help you discover!


Affirmations

Affirmations are powerful tools you can use to transform your dating and relationship life, whether you're single and mingling or already in a committed relationship.

Affirmations are positive statements that you repeat to yourself to foster a mindset of positivity and self-empowerment by rewiring your brain to focus on a belief in your ability to accomplish your goals and outcomes.

These mental shifts reshape your internal dialogue, motivate you to take action, boost your emotional well-being, and offer you the strength to pursue goals despite challenges.

Follow@pinkpositivedatingon Instagram for daily affirmations to transform your love life. These affirmations can you help build confidence in your ability to find a suitable romantic partner, build a strong positive mindset to succeed at modern dating, and help you attract and strengthen romantic relationships.


Psst...Want to see some action? 👀 We're on YouTube!


Timestamps

Want to hear more about the points highlighted in the blog? Use the podcast timestamps to easily navigate to something you want to hear more about in the show!

00:00 Letting Go of Dating Guilt and Shame

01:20 Reframing Singlehood and Societal Timelines

02:48 Reflecting on Past Dating Choices

05:06 Prioritizing Your Partnership Search

08:32 Navigating Relationship Breakups

09:27 Taking a Break from Dating

10:56 Thinking About Marriage Early On

12:37 Evaluating Good-on-Paper Partners

13:48 Expressing Needs and Boundaries

15:36 Dating Apps and Mixers

16:28 Women Making the First Move

17:55 Defining the Relationship

19:24 Recognizing Your Dating Standards

20:20 Big Pink Question


Modern dating got you down? No worries.

Say bye-bye to settling for less and hello to dating success! Check out our free ebook on the ten steps to overcoming singlehood, settling, and situationships.

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Psst...wanna know a secret?

Whether you're searching for love or strengthening your relationship, we've got the secrets to help you meet your dating goals. Navigate the modern dating scene confidently with real conversations on topics that matter. You in?

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Important Links

At Pink Positive Dating, our mission is to serve as a positive space for uplifting conversations of building happy healthy romantic relationships. Want to learn more? Check out the links below for insights, real conversations, and high vibes ✨

Next Steps

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