1. “So, are you dating anyone?”
If someone is excited about a person in their lives (and feels comfortable telling you about it), they’ll freely divulge this information. If not, don’t raise the question. We’ve gotten too accustomed as a culture to make relationship status one of the foremost definers of life accomplishments, and we can do a great deal of good by pausing before the temptation to inquire takes over this holiday season.
Ask instead: “Have you met any new friends or gone on any interesting trips / social outings since we last spoke?” If someone is in a life stage where there is a lot of transition, this may be a great conversation starter.
People who have moved or who have changed jobs may be engaged by a question like this. There are plenty of groups — organized and informal alike — that offer companionship to people who are single, and that’s as good a place to start as any to help them open up about relationships that matter — platonic or otherwise. Just don’t wink at them when you say friends. (I see you, mom.)
2. “When you least expect it, it’ll come.”
Moment of truth: this phrase sucks. Not only is it cliche, what does the recipient say in return? “Yes, you’re right. I’ll just keep sitting here none the wiser until “it” comes for me. Brilliant!”
It’s a passive, rhetorical statement that — at best — reminds us of how little we control when it comes to love; and, at worst, it can come off as dismissive or even condescending — as if there’s some secret you know to the ways of the world that they will only discover in hindsight once they’ve found love.
This phrase is often a placeholder for a more honest, meaningful conversation — or, nothing at all. You don’t need to offer assuring platitudes to be supportive of someone; change the conversation or ask a follow-up to something they already shared so that you don’t unwittingly offer unsolicited dating advice.
Say instead: Nothing. Even if you’re a psychologist or are a love doctor, the holidays aren’t the time to give advice where it isn’t requested. If you’re close to the person you are speaking to, connect with them on something they already said. Repeat back to them an experience they’ve shared.
If something sounds difficult, say it. “Wow, that must be tough” (if they’re talking about a trying dating experience) can be simple enough, then direct the conversation to something they enjoy doing. Or something like “I love seeing all the neat things you’re up to these days” can show that you’re attuned to— or interested in — the things that matter to them, that they feel in control of, and that they tackle on their own, sans partner.
Most importantly, listen. Active listening can solve the primary issue here by probing into something of worth or diverting a conversation rather than finding a band-aid phrase to inadequately cover a sticky subject.
3. “Can I play on your dating app(s)?”
A few drinks in, this ask often comes up. For those who have never had to use a dating app in their lives, the temptation creeps up. But curiosity killed the cat, right? While I’ve had a few hilarious examples of other people swiping on my behalf, it can go south quickly. Better to find other “games” to play, and keep the dating apps where they belong for the holiday: on the phone in your pocket or clutch.
Ask instead: Want to play scrabble?
4. “I could never be single in today’s day and age.”
You don’t have to tell us twice: the dating game has drastically changed. But you saying it aloud doesn’t make it any less true. It also isn’t exactly a comforting thought, nor is it necessary holiday conversation fodder. Rather than voicing something that may put another on edge — or repeat something that we’ve likely already heard, ad nauseum — skip the superficial sympathy card; I promise it won’t be a crowd pleaser.
Say instead: “How do you connect best with people at work or at home?” or “I know technology has changed how people communicate — what do you like and dislike about it? (How) does it affect you?” If you’re already on the topic of dating, you may likely be touching upon a broader topic of how people interact in modern society. Depending on the company, this may be a much richer conversation — and one that doesn’t put the focus solely on one party’s relationship status accounts.
5. “But you’re such a catch!”
So you agree, you think you’re really great? Glad we established that from the start. In all seriousness, this one really strikes a chord. It is almost always offered as a high compliment (thank you!) yet its bearers rarely consider how this may be misconstrued.
The reality is, when someone says this, it’s easy to think of this retort: “Ok, but if I’m such a ‘catch’, why has no one caught me yet?” They should appreciate the compliment but saying comments like this implies or assumes that someone should first do something or meet some standard to ‘deserve’ to be in a relationship. Steer clear of such assertions; they’re packed with a lot of hidden meaning.
Say instead: “I love [xx] about you.” If you’re going to give a compliment, you can make it more about the way the person in question makes you feel as a friend or family member.
Are they really good at cooking? Listening? Quoting random movies? Whatever makes them “a catch” in a romantic relationship also gives them an A+ in your book. Focus on the value a specific characteristic offers to a relationship that does exist — yours — rather than a theoretical, future-state one.
6. “You need to focus on yourself first before you find love.”
Like #5, this statement suggests that work must be done before someone is “worthy” or “ready” for a relationship. While it may be true that they are choosing to focus on themselves for a myriad of reasons, self-work and self-improvement are not a prerequisite for love. How many people do you know who met their significant others drunk at a bar? Not exactly a state of self-actualization. Those who are single will undoubtedly roll their eyes at this comment, so don’t be that person.
Say instead: “Tell me more about [something they’re doing for themselves.]” Let this be enough! If someone is actively pursuing something, taking a risk, or cultivating their own passions or talents, asking them to elaborate is bound to produce a great conversation. It doesn’t have to be tied to whether or not they’ll find a significant other.
Remember, even if a conversation may seem benign, it’s likely one that will be repeated often over the course of friendly small talk. Not only can that be emotionally exhausting for someone who may or may not already be guarded about the topic of relationships, but it can also discourage them from freely opening up about other things that excite them and bring them passion.
Most importantly, read the room and the conversation. Be authentic! There may be moments where broaching the topic of romance is, in fact, appropriate — and it may make the other person feel like you really care about their wellbeing.
Exert some generosity of spirit when celebrating their milestones and achievements — large or small — to offer solidarity and establish rapport before diving into the single / not single binary that makes those not in relationships cringe.
And practice restraint before offering advice that may come off as insincere: oftentimes the tension that surfaces during conversations about relationships stems from a feeling that one party is superior to the other because of their status as coupled or not. Be aware of this construct, so that you can genuinely connect with someone who happens to be single: It shouldn’t define them in the way that society facilitates today.
The more you can invite dialogue that taps into the parts of their lives they want to share, the richer and more engaging the conversation will be — no matter how brief. And wasn’t that the point in the first place? Avoiding the easy “low hanging fruit”questions like these — the ones that don’t really produce much value, in the first place — not only help you avoid awkward and sometimes offputting exchanges, they improve the quality of the conversations had altogether.
The best way to express gratitude this year — and always — is to meet people where they are, provide a warm and inviting atmosphere, and embrace differences while appreciating the unique contributions and individuality of those at the table, regardless of who is sitting by their side. Everyone will be thankful — and that’s a big win.