Engagement Season Survival Guide: for Men

It’s almost here. Tomorrow is Thanksgiving, which marks the first day of “engagement season”. At this point it doesn’t matter if engagement season was originally created as a marketing ploy or not, because the phenomenon has taken off in a big way.

Nowadays, over 40% of engagements happen between Thanksgiving and Christmas each year. However, engagement season technically lasts all the way through Valentine’s Day. Speaking of Valentine’s Day, Christmas Eve recently surpassed it as the most popular day to get engaged. This should give you an idea of how serious engagement season has become.

Depending on your status, engagement season can turn out a number of different ways. It can be a happy whirlwind and the beginning of the rest of your life with the one you love, it can be a heartbreaking disappointment, or it can be a very lonely and annoying few months. Read on for my advice on surviving this year’s engagement season.

If You’re Single

The woman on the far left has the same attitude as many singles during engagement season. Photo credit: Jezebel.
The woman on the far left has the same attitude as many singles during engagement season. Photo credit: Jezebel.

Be supportive. Your best friend might be insanely nervous about proposing to his girlfriend, your coworker might be worried that he purchased the wrong engagement ring, and your single cousin could be feeling sad and lonely.

Sometimes there’s extra bitterness associated with being single during this time of year. However, if they are or aren’t participating in engagement season, this time of year tends to make people reevaluate their romantic situation. This advice – to be supportive of your friends and family during the engagement and holiday seasons – really applies to anyone.

Take a social media break. You know it’s coming: the flood of Facebook and Instagram photos detailing every second of the proposal and every angle of the ring. If you’d rather not receive a painful reminder that you’re single every time you log in, now’s the time to take a breather from social media.

Try dating again. I’m sure you’ve either heard about or experienced being single at a wedding. Weddings are notorious for making singles re-think their situation and decide to meet some new people. Think of engagement season as a wedding that lasts 3 months. Love is in the air, and it’s a great time to couple up. A lot of single people are looking around, feeling left out, and wanting to put themselves on the market again.

If You’re Planning a Proposal


Lock down your location. It’s important to have your proposal spot planned out in advance if you’re popping the question during engagement season. You don’t want to leave things to the last minute, especially if you want to propose at a popular restaurant or landmark.

Give advance notice. Make sure that anyone who needs to know about the proposal ahead of time knows when and where it will happen. This is especially important if you’re planning on proposing on a holiday. You don’t want to upstage other plans, have yours upstaged, or give your future in-laws the surprise of their life.

Consider a Christmas proposal. You have the ring, you’ve planned the proposal, and you just realized that in all the excitement of researching and picking out the perfect engagement ring you forgot to get your significant other a present. If you didn’t have a specific date in mind, you might want to opt for a Christmas Day or Christmas Eve proposal. This way the present and the proposal are all wrapped up into one! 

If You’re Getting Pressured

If you have a significant other and you’re getting pressured to propose outside of engagement season, it’s only going to get worse being around family and friends who are getting engaged. You can handle engagement season pressure the direct way, or the indirect way.

If you’re a direct person and you know for sure that you’re not going to pop the question this engagement season, get ahead of the pressure and let everyone (including your significant other!) know that this is not the time. This way, no false expectations are set.

If you’d rather not take the direct approach, it’s best to avoid situations that will become uncomfortable during engagement season. In terms of gifts, it’s probably best to stay away from the jewelry category overall. However, if you do want to give her a fine jewelry gift, be clear about what kind of jewelry she will be receiving to prevent disappointment.

If You’re Shopping for an Engagement Ring 

halo engagement ring

Start snooping. Before you jump into the finer points of researching an engagement ring, it’s time to start playing detective with your significant other. Size up her style by looking at her wardrobe, jewelry collection, and Pinterest. Does she seem traditional, modern, vintage, or more offbeat? You want to make sure her engagement ring is special to her, so make sure to consider multiple style profiles and use a free in-store preview to see engagement rings direct in person before you decide on it. A whole lot of ring comparison goes on during engagement season, so a unique engagement ring is immensely important. Unlike James Allen engagement rings, you can see your Ritani ring in person without making a purchase.

You should also take a ring from her jewelry collection so you can figure out her ring size. At Ritani, we offer both a handy ring sizer tool and free ring resizing services, so our customers’ proposals will be nothing less than perfect.

Get your diamond education. The most difficult part of shopping for an engagement ring is often figuring out which diamond or gemstone is the perfect fit, for style and budget. You should learn your 4Cs and determine which 4C grades will be most important to you and your partner before you start shopping for loose diamonds. Sales associates at engagement ring stores will often be helpful and teach you the basics, but don’t let them pressure you into buying before you’re ready.

Take advantage of engagement season perks. Reputable diamond sellers all over the world have had to adapt to keep up with the high demand of engagement season. As the customer, you should definitely take advantage of all the perks and features that retailers have during this time of the year.

Shipping and return dates can be tough to negotiate during engagement season. You want to start early enough that you have the perfect engagement ring in mind, but you also have time to think long and hard about your decision before you pop the question. Starting on November 15, Ritani has been offering an extended return period.

For the more impulsive folks out there, reputable jewelers usually have extended shipping dates, as well. I advise against making an impulse buy of an engagement ring, but if the timing works out so that you need to order one by the holidays and it’s down to the wire, Ritani’s last day to ship is December 23.

Do you know anyone who is proposing or getting engaged this engagement season? Did you? Feel free to share photos, stories, and any extra questions in the comments below!