Benny Lichtenwalner

Should I plan something for my ex on special occasions?

By Benny Lichtenwalner, breakup coach & author ofHow to Get Your Ex Back · Updated2026-08-05

Short answer: No. Valentine's Day, anniversaries, and holidays are for couples. Using them as an opening before you're officially back together frames you as the one waiting for permission. If the relationship is ready, she'll bring it up. Your job is to be available when she opens the door, not to engineer the occasion.

Should I Plan Something for My Ex on Special Occasions?

No. And understanding why “no” is the answer reveals a lot about what actually works during the reconnection phase.

Benny Lichtenwalner, breakup coach and author of How to Get Your Ex Back, names this one of the most common errors once re-engagement has started: using a calendar event (Valentine’s Day, an anniversary, a holiday) as a justification for initiating contact or engineering a meeting. The occasion feels like a natural opportunity. But special occasions are socially coded for couples, and invoking one when you’re not officially a couple again communicates exactly that gap.

When Does an Invitation Actually Work?

Invitations work when they emerge from a genuine shift in her energy toward you, not from a date on the calendar. The threshold is specific:

Signal What it means Your move
She’s initiating texts more often Her nervous system wants proximity Receive it; don’t immediately capitalize
She’s less impatient, more playful The guard has lowered Match her energy; stay light
She creates a logistics excuse She’s testing whether you’ll open the door Read her openness carefully before acting
She references something you’d do together She’s placing herself in your future Note it; don’t push on it immediately
She brings up a holiday or occasion first She’s signaling she’d like to mark it with you Respond warmly; let her take the lead

The key: she creates the opening. You don’t manufacture one.

Why Don’t Special Occasions Create That Opening?

Because they carry built-in expectations — and she knows that. When you suggest something for Valentine’s Day before you’re officially together again, the subtext isn’t I want to celebrate you. It’s I’m waiting for permission to be your partner again. That’s the wrong frame. It positions you as someone seeking confirmation rather than someone who doesn’t need it.

Holidays raise emotional stakes in contexts where she hasn’t signaled she’s ready for those stakes. That raises pressure exactly when you need to be the low-pressure option.

How Should I Handle Specific Situations?

  1. When she creates a logistics opportunity (returning something, a shared errand): read the energy. If she’s warm and seems open to more time, invite her in or extend slightly. If the signal is neutral, let the logistics be logistics.
  2. When you’re unsure whether to suggest a meeting: meeting her at a venue is almost always the safest option. It creates less emotional depth prematurely, keeps the frame light, and gives her agency over whether she comes to you.
  3. When you’ve spent time together recently: don’t push for the next thing. Pull back and let her initiate. Time together is a deposit; immediately spending it undoes what you built.
  4. When she signals openness to a holiday together: respond warmly, confirm you’d enjoy that, and let her do the logistical work. You’re available. You’re just not the one making it happen.
  5. When it’s a romantic occasion she hasn’t mentioned: don’t bring it up. If she wants to mark it with you, she will.

What Should I Avoid Doing?

What Does This Look Like in Practice?

Two clients, both in the reconnection phase after successful no-contact, faced the same decision around a holiday that fell about six weeks into rebuilding contact. Both were seeing warmer signals — their exes had initiated the last several messages, tone had shifted from neutral to playful.

One used the holiday as a reason to suggest plans. His ex replied warmly but noncommittally and pulled back slightly in the days that followed. The calendar event had raised emotional stakes before she was ready for them.

The other client sat on the holiday entirely. His ex, noticing he hadn’t made it awkward, brought up a casual plan a few days later on her own terms. They spent time together in a low-pressure context. The momentum continued from there.

The difference was who controlled the pace.

Related questions

What if my ex seems open to celebrating together? Should I suggest it?

Only if she's the one who brought it up. If she's asking what you're doing for Valentine's Day, she's testing the water. Respond warmly and leave the door open. But don't engineer the occasion yourself; that moves you into chasing territory.

When is it appropriate to plan something with my ex in the reconnection phase?

When her energy has shifted warmer (she's initiating more, responding faster, her tone has changed) and you've already spent time together. The combination of those signals is the green light. The occasion can be simple; the signals are what matter, not the event itself.

What do I do when she creates a logistics excuse to reach out?

Read her openness carefully. If the energy is warm and she seems receptive to more time, use the logistics moment as a light opportunity. If the signal is ambiguous, let it pass cleanly. Don't force proximity when the invitation isn't clear.

After we spend time together, how long should I wait before suggesting the next thing?

Don't suggest the next thing at all. Let her initiate. Spending time together is a deposit. Immediately pushing for the next meeting spends that deposit. Pull back and see what she does with the space.

What if no natural occasion comes up during the reconnection phase?

Then nothing happens and you continue building. Not every phase has a natural occasion, and forcing one creates more problems than it solves. Your posture during this phase is what creates attraction.

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