I have been to a lot of weddings. I calculated and I think I've attended more than 200 weddings in a professional capacity over the last decade. What I've learned is that while they are always lovely, inevitably, when the time comes for toasts, I find myself looking for a place to hide and hoping that no one will say anything that will make me (or the bride, groom or anyone else) wish that a giant hole would open in the ground and swallow me up to save me from the embarrassment of listening to a horrifying wedding speech.
I've catalogued my favorite "bad toasts" from over the years, and have found that, amazingly, the most awkward and offensive speeches nearly always fall into one of five topic areas. Should you be asked to make some remarks at a wedding, or are thinking of taking the mic up at your own wedding, here are five topics that should be avoided ... at any and all costs.
1. Past Relationships: Few things evoke more quiet gasps of horror than when a best man or maid of honor begins to take a trip down the romantic memory lane of the bride or groom's single years. I still shudder when I think about one wedding where the MOH (maid of honor, to you wedding novices) started on "Remember that guy you used to sleep with in college? He strung you along for years!" This doesn't just apply to friends; it was equally awkward standing in the audience when a groom told his now-bride how happy he was that he had called off his past three engagements but that he made it to the altar with her. I don't know that any of us needed to know or to be reminded of that.
2. Money: Generally speaking, little evokes horror quite like bringing up cash during a toast, even if it seems the intention is complimentary. So, no matter how amazing or lavish the wedding might seem, a good opener is probably not "Wow! This must have cost them a fortune, Huh?" (I've heard that). Even if your relationship with the couple is particularly intimate, and you are mesmerized by their generosity, one should avoid making mention of monetary transactions at a wedding. I'm reminded of a particularly awkward toast where, when describing the couple's generosity, the Best Man made mention of a large business loan they made to him for a business that didn't take off, and added, "they are still the only people I haven't paid back!"
3. Low Lights of Bride and Groom's Relationship: Many couples have long and winding roads towards the altar. Blame it on the follies of youth, or travel or distance, lots of factors can make the early stages of a relationship bumpy and possibly comedic. While this might be great conversation for dinner with the couple alone, it probably isn't great to remind everyone in a public setting about the time that the groom cried all night because he had been cheated on by the bride before he took her back. Or about the time they broke off their relationship because her future mother in law couldn't stand her. The wedding day is a day for joy about the future, not triumph over adversities of the past ... even if they are funny.
4. Your own failed marriage: Listen, the world is full of realists, so no one wants you to pretend that divorce doesn't exist, but it would be best, and less awkward to not introduce your own failed marriage into your toast, even if the intention is complimentary. Some examples of this are: "If I would have had a woman like Janet, well, I think maybe my marriage would have ended differently. Or maybe not ended at all." Or, my personal favorite, that still haunts me years and years later "When I was on my way here today, I looked at my wife and, we'd been fighting earlier, and I thought to myself "I really hope that this marriage thing works out better for them than it did for us." Not really necessary. I think this is doubly true for parents. Obviously, your child is aware that you and their mother or father is divorced. Likely, the awkwardness was palpable during the planning process. You needn't wish her or him better luck than the two of you had. It's implied and needn't be verbalized.
5. How you NEVER thought you'd see this day and other Insultaments: "My brother is such a jerk, I really never thought ANYONE would want to be with him each and every day." Or, "We had resigned ourselves to thinking of Beth as a Career Girl." In my family we call them Uncle Johns, after my uncle who was the master of the well-intended insultament. You know the insultament: it's a compliment wrapped in an insult. Ironically it's almost always the parents or siblings who are guilty of this element of embarrassing speech-making.
Remember, giving a toast at a wedding is not only an honor, it's a commitment to not dropping the ball! The whole party stops for your words, so make the most of it and avoid the low-hanging humor fruit. To quote Owen Wilson in Wedding Crashers, you are always "better off going with something from the heart."