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[Navigating Holiday Heartbreak and Dating Dynamics]-[DATING DURING THE HOLIDAYS: reaching out to your ex, breakups, bringing your bf/gf home, and gift guide - ADVICE SESSION #14]

Trying Not to Care · B2 · 2025-11-17

RelationshipsHealthCareers
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📋 Summary

Surviving the Holiday Season: Advice on Breakups, Family, and New Relationships

Navigating the holiday season while dealing with relationship complexities can be "excruciating." Whether you are mourning an ex or navigating the early stages of a new romance, the pressure of the holidays often amplifies existing emotions. In this episode, Ashley provides practical advice on how to manage these challenges with self-respect and clarity.

The Pitfalls of Reaching Out to an Ex

Ashley firmly advises against texting an ex during the holidays. While the urge to reach out often stems from missing the person or seeking an excuse to reconnect, she emphasizes that "the holidays don't change the reason why you broke up." Attempting to bridge the gap during this time is often a "disaster" waiting to happen. The risk of receiving a cold response—or no response at all—can "ruin your Christmas" and set back your healing process. She warns that the holidays are "mourning and grieving on crack," and it is crucial to recognize that just because you miss someone doesn't mean they "deserve a place in your life."

Communicating Breakups to Family

One of the most stressful aspects of the holidays is facing family after a breakup. Ashley admits that in the past, she avoided being honest to prevent uncomfortable questions or judgment. However, she now advocates for radical honesty. Telling your family in advance allows them to support you rather than bombarding you with questions at the dinner table. She notes that family members are often "nicer to you" when they are aware you are hurting, providing a space for love and care rather than unwanted scrutiny. "Don't doubt the love that your family can give to you if you're just honest with them."

Coping with Loneliness and Traditions

When it comes to missing an ex, Ashley suggests allowing yourself to feel the sadness without letting it dictate your holiday experience. Suppressing emotions only "delays the healing journey." Instead of fixating on past traditions, she encourages creating new memories. If a specific activity feels tied to an ex, reclaim it by doing it with new people. "Make it about your new life, not your past life." She emphasizes that you have lived a full life before that person and you are capable of enjoying the holidays without them.

Navigating New Relationships and Gift-Giving

For those starting new relationships, the question of when to introduce a partner to family is significant. Ashley suggests that this step should not be rushed, as it increases the level of "accountability" in the relationship. It is a "sacred" step that should only be taken when both partners are on the same page.

Regarding gifts, her rule of thumb is simple: "If there's no label, there is no gift." She argues that a "situationship" does not warrant the privilege of gift-giving. If you are in a committed relationship, focus on thoughtful, sentimental items rather than extravagant, expensive ones. "The gesture is the most important thing." If you are unsure of where you stand, have the uncomfortable conversation before the holidays arrive. It is better to face the reality of the situation than to harbor resentment because of unmet expectations.

Ultimately, Ashley encourages listeners to "romanticize your life" and prioritize their own well-being. The holidays are a time to lean on those who truly choose you, and the best path forward is to focus on your current life rather than dwelling on the past.

🎯Key Sentences

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I'm gonna be so honest with you.
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Things naturally remind you of them.
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I wonder how they are.
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📝Key Phrases

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right around the corner
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more times than not
3
check in on
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rekindle things
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fresh wound
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📖 Transcript

Hello, welcome to welcome back to trying not to care if you're new here.
My name is ashley and i upload every single monday and every now and then i do a q a or an advice session where i ask you what you want to ask me, and i usually pull these questions from my instagram.
I'll ask my story and if you see the story and you have a question and you ask me that question and i like that question, I will answer it.
So this month's advice session is all about dating during the holidays because, let's be real, dating during the holidays is excruciating.
It is so hard.
Even if you are in a long-term relationship and everything's going swell, the holidays can sometimes be a headache.

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