A Guide to Selecting the Perfect Plus One for Every Wedding

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One of the most important choices a person must make in the lead-up to a wedding does not involve a new dress or hotel accommodations or travel arrangements, and it certainly has nothing to do with what to give the happy couple. Well, unless you’re giving the happy couple the pleasure of the company of the person whom you have chosen to bring to their wedding. Or the distinct lack of pleasure in that company, should you choose wrong.

In my lifetime of going to weddings, which I write about in Save the Date: The Occasional Mortifications of a Serial Wedding Guest, there have been good dates and bad dates and sometimes no dates at all (and that’s been good and bad, too; sometimes it’s been both at the same wedding). Your invite should make this clear whether or not you’ve been invited plus — if a date’s not mentioned, you didn’t get a plus one, and Emily Post would advise you not to ask for the option, though I admit to having done this in the past (Mortification #267). But, if the presence of both you and a companion of your choosing has been requested, here’s your guide to selecting the best possible escort for your upcoming event.

Destination in the tropics, requiring a flight and hotel stay

Who to Bring: It is tempting, when invited to this sort of wedding, to look at your dwindling bank account and think, “What lucky fellow or lady can I force to come with me to split the cost of the hotel room?” I feel ya. I have done this. And this is why I suggest bringing someone who is very, very rich, who can afford not just your room but also his own, because then you don’t have to like him, you can just use him for his money. What? No. I do not suggest that at all. That’s terrible advice! But, um, yes, this money situation is real, right? So I suggest, if you have a fellow or lady who you’re feeling pretty good about these days, invite that person and stay for some extra days and make a vacation of this trip, because that’s what it can be, too. If you do not have such a person, go alone. You will be enveloped in the typical destination-wedding atmosphere of love and harmony and camaraderie and insta-friend-ness. You will not feel alone, you will simply feel happy, and if you don’t, there will be coconut cocktails and plenty of Vitamin D to fix that problem.

Why: Because love in the tropics is grand, but the tropics are grand either way. Especially after this winter, amirite East Coast America?

Who Not to Bring: Someone who does not play nicely with others; someone who insists on wearing a T-shirt as bathing suit cover-up while in the pool.

High school friends in your hometown, the one you haven’t been back to in years

Who to Bring:Oh, this gets dicey. You’re going back to a place that represents a former you, and that can bring out all sorts of insecurities and concerns you don’t normally have in your productive, successful, super-cool and completely self-actualized current life. You may think that the answer here is to bring some date who will really impress your old pals, like a movie producer or B-list actor or guy who just sold a book about going to weddings (note: this man does not exist). But if you choose based on status, and who you’re hoping to impress, you run the risk of ruining the wedding for not only you but also your old friends who really just want to see you and catch up. So if you’re dating someone you adore, bring that person.

Why: This is like a reunion. Just be you. You will learn important things about yourself, free from having to take care of a date. It may not be fun, but it will be good for you.

Who Not to Bring:A guy who just sold a book about going to weddings. He is my date, thank you.

The one where everybody but you is married

Who to Bring: Unlike in the above scenario, this is a situation in which you should bring a date. A wedding where everyone else is married — especially if you yourself are feeling a bit like you wish you were there, too, whether you’re ready to admit that or not — can be something of an emotional powder-keg, and you need a stabilizing force here. Choose your best guy friend, the one who always comes through in a pinch and hangs up your shelves when you need that sort of thing done but to whom you have no romantic attraction, because things aren’t always the way they are in the movies, and that’s totally fine.

Why: Safety in numbers, a shoulder to surreptitiously cry upon.

Who Not to Bring: A married person as your date.

The one where there’s just one single guy (and the bride tells you about it beforehand)

Who to Bring: No one, silly, that one single guy is YOURS. The bride basically labeled him with your name, and he’s going to be seated next to you at the dinner table, and you’ll cut him tiny bites of your chicken and he’ll give you his steak and then you’ll walk around for the rest of the night with your arms around each other as if you really were dates. (Yes, this actually happened.)

Why: It is fun and exciting to meet new people at weddings, and maybe to kiss them, too.

Who Not to Bring: Your boyfriend, because that could get awkward.

The wedding of a coworker that you didn’t think you’d get invited to but did

Who to Bring: If we were playing Uno (remember Uno?), this is where I’d play the wild card. By which I mean, this is a surprise wedding, a wedding-extra. You didn’t think you’d be invited, maybe you didn’t care, but now that you are, you should go and you should also bring a date — a friend, a person you are sleeping with but also get along with quite well in public, a boy- or girlfriend, or possibly even another coworker who has also been invited and whom you like.

Why: Seeing coworkers in non-work situations can feel very strange and uncomfortable, and having someone by your side who you know personally can help bridge the weird gap between work and play that this wedding represents. It is also handy to have someone around who can say, “No, Jen, don’t do a third tequila shot and then jump in the pool with all your clothes on in the presence of the head of human resources.”

Who Not to Bring: The guy your boss just fired.

The one to which you are required to go, despite having just survived a breakup and trying to avoid thoughts of love, relationships and how you may or may not have failed

Who to Bring: First, ugh. I am sorry. I have been there. Second, do not hire a male escort and pay him $6,000 like Debra Messing did in The Wedding Date; he will not fall in love with you and give you a discount. Instead, save your money for a new dress and shoes that will make you feel like a million bucks. And, if you can manage it, go alone.

Why: Remember how earlier in this piece I was like, going alone is good for you, you will learn things about yourself? Well, this is one situation in which you are still feeling pretty raw emotionally, and it’s going to be hard to go to a lot of things alone, especially an event that’s about two people who are in love and promising togetherness. But, you will get through it and you will feel stronger and better for having done it. Go, and go alone. You will be really proud of yourself. (And bring tissues. It’s O.K. to cry, and it’s even more O.K. to cry at weddings.)

Who Not to Bring: The ex. Good lord, do not do that.

The one to which you haven’t been asked to bring a date

Who to Bring: Pair up with someone else who’s invited, man or woman, and share a hotel room with said individual to save on the cost, if you like. You can, I do believe, ask the bride or groom what single folks have been invited whom you might know; I have done this with no negative repercussions.

Why: This will eliminate your showing-up-alone wedding anxiety as well as the sudden need to “prove how in love you are with your date” that can occur in otherwise sane people at weddings. You have a built-in pal who adds no pressure for romance to happen. Also, two words: Wing woman.

Who Not to Bring: A date. Refer to the opening paragraphs of this piece for more on why.

Jenn Doll, author To hear about Moritifcations #1-266, pick up Jen Doll’s new hilarious and heartfelt new book Save the Date: The Occasional Mortifications of a Serial Wedding Guest. Out now!

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