Benefits Timing: The Best Month to Get Married, Divorced, or Have a Baby

There’s something slightly absurd about planning major life events around your employer’s benefit periods, but ignoring these timing considerations can cost you thousands of dollars. The reality is that employee benefits operate on rigid calendars with specific enrollment windows, waiting periods, and qualification dates. When life events intersect with these schedules in unfortunate ways, you can find yourself temporarily uninsured, missing out on dependent care subsidies, or paying dramatically more for coverage than you would have if the timing had been slightly different.

Nobody wants to schedule their wedding around open enrollment or delay starting a family because of FSA contribution deadlines. But understanding how benefit timing works—and when you have flexibility to optimize—can help you avoid expensive mistakes and maximize the value you get from your employer’s offerings.

The good news is that major life events typically trigger special enrollment periods that let you make benefit changes outside the normal annual window. The challenge is understanding exactly how these special enrollment periods work, what documentation you’ll need, and how different events interact with various benefit programs in ways that can either enhance or diminish their value.

The Wedding Date Decision

Getting married gives you a qualifying life event that allows you to add your spouse to your health insurance, adjust your FSA contributions, and make other benefit changes outside of open enrollment. But the timing of when you actually get married within the year can have significant financial implications.

Fourth quarter weddings (October-December) create complications: If you get married in November, you can add your spouse to your insurance immediately, which is great. But you’ve also just entered the window where you need to make decisions about next year’s benefits during open enrollment. You’re making these decisions with very limited information about your new household circumstances.

Should you switch to a family plan? What about your spouse’s insurance—is it better? How should you adjust FSA contributions when you don’t yet know what your combined medical expenses will look like? You’re making consequential financial decisions about a marriage that’s only weeks old.

Early-year weddings (January-March) offer more clarity: Get married in February, and you have nearly a full year of married life before you need to make decisions about next year’s benefits during open enrollment. You’ll understand your combined healthcare usage patterns, have clarity about whose employer’s insurance is better, and can make informed decisions about FSA contributions based on actual experience rather than guesses.

Mid-year weddings (April-September) are the sweet spot: You get the special enrollment period to add your spouse immediately, but you also have several months to understand your combined benefit needs before open enrollment arrives. If you discover that your spouse’s insurance is significantly better, you have time to plan the switch for the following January. If you’re thinking about using dependent care FSAs for future family planning, you have data to inform those decisions.

For benefits platforms with more flexibility: Modern benefits administration systems have made some of these timing issues less critical. If you’re working with a company that uses flexible benefit solutions, understanding how Benepass can help with life event transitions is valuable—platforms designed for flexibility often allow easier adjustments as your circumstances change, reducing the penalty for less-than-optimal timing.

The Divorce Timeline

Divorce is obviously not something you time around benefit periods, but understanding the benefit implications of when a divorce is finalized can help you plan for coverage gaps and avoid expensive mistakes.

December divorces create immediate benefit impacts: If your divorce is finalized in December, you’re losing spousal coverage (or your ex is losing coverage under your plan) right before open enrollment. This is actually decent timing because you can immediately adjust your elections for the following year during open enrollment, selecting single rather than family coverage and adjusting FSA contributions accordingly.

January-November divorces require active management: A divorce finalized in June means you need to remove your ex-spouse from your insurance and adjust your coverage immediately through a special enrollment period. This mid-year change affects your payroll deductions for the remainder of the year. You’ll also need to revisit these decisions again during the next open enrollment, but at least you’ll have several months of data about your new single-household expenses.

COBRA timing considerations: If your ex-spouse was covered under your insurance, they’re eligible for COBRA coverage, which can extend their coverage for up to 36 months. However, COBRA is expensive—typically 102% of the full premium cost. The timing of when COBRA eligibility begins matters significantly for your ex’s financial planning, though it’s unlikely to be the determining factor in when you finalize a divorce.

The HSA complication: If you’ve been contributing to a Health Savings Account as a family, divorce affects your contribution limits. The annual contribution limit drops from the family amount ($8,300 in 2024) to the individual amount ($4,150 in 2024). If your divorce is finalized late in the year after you’ve already contributed at the family rate, you might have excess contributions that create tax complications.

The Baby Timing Question

This is where benefit timing gets really complicated, because while you can’t precisely schedule when a baby arrives, you do have some control over when you start trying to conceive—and understanding the benefit implications of different birth timing can be valuable.

December babies are expensive from a deductible perspective: If your baby is born in December, you’re potentially paying deductibles and out-of-pocket maximums in two different plan years. The prenatal care, delivery, and immediate postnatal care hit your current year’s deductible. Then January 1st arrives, your deductible resets, and any early complications or pediatric care start working toward a new deductible. From a pure financial optimization perspective, December births can be costly.

January babies are financially optimal: A baby born in early January means almost all pregnancy-related medical expenses—prenatal care, delivery, postnatal care—occur within a single plan year. You’re only working toward one year’s deductible and out-of-pocket maximum rather than splitting expenses across two years. Once you hit your out-of-pocket max (which you’re likely to do with childbirth), everything else that year is covered at 100%.

But there are counterarguments to January timing: If you know you’re going to hit your out-of-pocket maximum anyway (which is very likely with childbirth), having the baby later in the year means you’ve satisfied your deductible and OOP max, so any other medical needs for the rest of that year are fully covered. If your older child needs surgery, if you have an accident, if any other medical expense arises—it’s covered at 100% after you’ve already hit your maximum.

FSA timing for dependent care: Dependent Care FSAs are use-it-or-lose-it and can only be used for care expenses actually incurred. If your baby is born in December, you can’t contribute much to a dependent care FSA for that year since you’ll only have one month of eligible expenses. But you can elect the full amount for the following year. If your baby is born in January, you have eleven months of potential dependent care expenses to fund with that year’s FSA.

Parental leave considerations: Some companies’ parental leave policies are based on calendar years—perhaps you get 12 weeks per year. A baby born in December means your leave extends into January, potentially using leave allocation from two different policy years. A baby born in January means your entire leave falls within a single policy year, preserving the following year’s leave balance for potential complications or a future child.

The Open Enrollment Window Itself

Beyond timing major life events, simply understanding when your company’s open enrollment period falls can help you plan other benefit-adjacent decisions.

Medical procedures and open enrollment: If you’re planning an elective medical procedure or know you’ll need a significant medical expense, timing it relative to open enrollment matters. Schedule it after you’ve elected your benefits for the year—including appropriate FSA contributions—so you can fund it with pre-tax dollars. Scheduling a procedure in October before November open enrollment means you can’t fund it with next year’s FSA; you’re stuck using post-tax dollars or this year’s FSA if you happened to contribute enough.

Job changes and open enrollment timing: If you’re considering leaving your job, doing so right before your new employer’s open enrollment period can be beneficial. You’ll get a special enrollment period as a new hire, allowing you to select benefits immediately, and then you’ll have the option to adjust those elections during open enrollment a few weeks or months later once you better understand your needs. Joining a new employer right after their open enrollment means waiting nearly a full year before you can make changes (unless you have another qualifying life event).

Documentation and Deadlines

Regardless of which life event you’re experiencing, understanding documentation requirements and deadlines is critical.

You typically have 30-60 days: Most qualifying life events give you 30 to 60 days from the event to make benefit changes. Miss this window, and you’re stuck with your current elections until the next open enrollment. This matters enormously—if you have a baby and forget to add them to your insurance within the qualifying period, they’re uninsured until open enrollment arrives, which could be nearly a year away.

Documentation is required: Marriage certificates, divorce decrees, birth certificates—you’ll need official documentation of your life event to make benefit changes. Start gathering this documentation immediately after the event, because benefits offices won’t process changes without it, and delays can be costly.

Different benefits have different rules: Your health insurance might allow 60 days to add a new dependent, but your FSA changes might need to be made within 30 days. Each benefit type can have different qualifying life events and different deadlines. Check with your benefits administrator to understand the specific rules for each program.

The Takeaway

Nobody’s suggesting you should plan your wedding date, divorce timeline, or when to have children primarily around your benefit periods. These are life decisions driven by personal, emotional, and practical considerations far more important than marginal benefit optimization.

But within the constraints of your actual life circumstances, understanding how benefit timing works can help you avoid costly mistakes and make informed decisions about when you have flexibility. Getting married in March instead of November might save you thousands in insurance premiums and FSA contribution errors. Understanding that December births create two-year deductible exposure might influence your financial planning even if it doesn’t change when you have the baby.

The key is awareness. Know when your open enrollment period falls. Understand the special enrollment rules that apply to your major life events. Document everything immediately. Make benefit changes within the required windows. And when you do have some flexibility about timing—whether it’s scheduling an elective procedure, planning a wedding, or other life events with some temporal flexibility—consider how that timing intersects with your benefit calendar.

It’s slightly ridiculous that we need to think this way, but employer benefits are too valuable to ignore. A little strategic awareness about timing can translate into thousands of dollars of value—or help you avoid expensive mistakes that could have been prevented with slightly different timing.