🦉What Valentine’s Day Can Teach Us About Why M&A Deals Fail

The hidden cost of assumptions in deals and relationships.

Author

Paloma Goggins
February 13, 2026

Every year around Valentine’s Day, the same thing happens.

One person has a very clear picture in their mind of how the day should go.

The dinner reservation.
The flowers.
The level of effort.
The feeling they expect to walk away with.

The other person has a completely different picture (or no picture at all).

No one says it out loud.

And when reality doesn’t match the expectation, disappointment follows.

Not because someone was inherently wrong, but because the expectations were never aligned in the first place.

We see the exact same dynamic play out in deals.

A business owner spends months (sometimes years) imagining what life will look like after selling their business.

More freedom. Less stress. Time to pursue something new. The vision becomes so clear internally that it starts to feel like part of the deal itself.

The problem is, that vision often never gets communicated.

Not to the buyer. Not to advisors. Sometimes not even to themselves in concrete terms.

Then the deal closes.

And instead of relief, the seller feels unsettled. Disappointed. Occasionally even regretful. The transaction delivered exactly what was negotiated, but not what was expected.

Deals rarely fall apart because of what’s written in the agreement. More often, they struggle because of what was never said.

Just like in personal relationships, successful deals start with aligned expectations.

Getting to know the buyer and seller beyond an email signature isn’t a luxury; it’s essential.

Misunderstandings around timeline, purchase price adjustments, or transition support can quietly derail even the most promising transactions when assumptions replace conversations.

Below are 3 ways buyers and sellers can set clear expectations early in the process:

1. Break Bread

Valentine’s Day works best when people slow down and actually spend time together. The sale of a business is no different.

In a world where transactions increasingly happen over email threads and Zoom calls, getting to know the person on the other side of the table has become a lost art.

Taking time for face-to-face conversations early helps both sides determine whether the deal should move forward at all. It surfaces misalignment before it becomes expensive and creates space to set realistic expectations for how negotiations will unfold.

When both sides understand not just the numbers, but the people behind them, the path to closing becomes far smoother

2. Set Realistic Goals

Many Valentine’s Day disappointments come from timelines and expectations that were never realistic to begin with. Same goes for deals.

A clear and realistic timeline sets the tone for the entire transaction. While most deals include a projected schedule in the Letter of Intent, that timeline should be viewed as a roadmap (not a rigid deadline).

Extensions and amendments are common and shouldn’t create anxiety. Careful diligence, review, and negotiation take time, and that attention to detail is often what protects the economics and long-term success of the transaction.

Realistic deadlines help keep the peace while important negotiation takes place.

3. Plan for Life After Closing

Closing is a milestone, but it’s also a moment of vulnerability for both parties.

For sellers, stepping away from something they’ve built over years can feel disorienting without a clear sense of what comes next.

Will they remain involved? Step back gradually? Or move on entirely?

For buyers, the questions are just as personal.

Will the seller remain available if challenges arise?

What happens if key employees leave or performance shifts during the first 90 days?

A thoughtful post-closing plan answers these questions before they turn into anxiety. When sellers invest in a meaningful transition and buyers understand what support looks like, confidence replaces uncertainty. And when sellers have something to look forward to beyond the deal, closing feels less like an ending and more like personal evolution.

Valentine’s Day disappointments rarely come from bad intentions. They come from expectations that were never disclosed.

When expectations are clear, both relationships and deals have a much better chance of playing out exactly the way both sides hoped things would.

And in a world where fast is often mistaken as better, remember:

The strongest transactions aren’t defined by how quickly they close, but by how thoughtfully they’re built.

Enjoy the read? It was inspired by Episode 23 of of Merger She Wrote episode (30 minutes):

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