Tag Archive for: advice for the holidays

Single for the Holidays? Here’s How to Handle Nosy Family Questions

Holidays can be heartwarming—gathered around the table, enjoying laughs, and sharing stories. But for singles, they can also bring relentless questioning.

“Why are you still single?” or “Are you dating anyone?” suddenly become the headliners of family conversations. If this sounds familiar, you’re not alone in dreading that annual pressure.

Let’s unpack how to navigate these moments with grace, humor, and confidence.

Understanding Family Dynamics

Whether it’s your chatty aunt or a curious cousin, families love updates. Often, this stems from a genuine concern or love for you.

However, the constant focus on your relationship status can feel isolating if you’re single. Families tend to project their views about milestones—relationships, marriage, kids—onto younger generations.

It’s less about personal attacks and more about their expectations of “what’s next” for you. But that doesn’t make it any easier to sit through.

Common Questions You Might Hear

Here’s a sneak peek at the greatest hits you might hear this holiday season:

  • “Why are you still single?”: Often said as though your relationship status is a puzzle to solve.
  • “Have you tried dating apps?”: As if they’ve cracked modern romance.
  • “Don’t you want kids?”: A question that could not feel more personal.
  • “I know someone perfect for you!”: Cue the awkward blind-date matchmaking.

No matter the intent, these phrases can feel invasive.

The Pressure of Expectations

Family dynamics create moments where expectations rise like an invisible fog.

For singles, there’s often the unspoken assumption that the ultimate life goal is finding a partner. If you’re content in your singlehood, it might feel invalidated by repeated questioning.

The result? Stress, self-doubt, or frustration by the time dessert is served. Understanding this dynamic can help you take a compassionate approach—even as you find strategies to manage the discomfort.

Coping Strategies for Singles

Here are ways to shield your peace when conversations about your singlehood arise.

Prepare Your Responses

Having a response ready makes unexpected questions much less awkward. Use humor, honesty, or even deflection, depending on the mood:

Humor: “I figured I’d save room at the table for extra pie instead of a partner.”

Honest but firm: “I’m happy where I am right now—thanks for asking.”

Playful: “Still single! Any takers here know Prince Harry’s backup cousin?”

Practice these responses ahead of time to deliver them calmly and with a smile.

Shift the Focus

When conversations veer into uncomfortable territory, subtly change the topic. Ask about their hobbies, interests, or holiday plans. It’s easier to dodge questions when you steer the conversation elsewhere. For example:

“Enough about me! How’s your new project going?”

“Speaking of relationships, how did you and Uncle Bob first meet?”

Redirecting the spotlight can take the pressure off you.

Practice Self-Care

Family gatherings can be draining, so prioritize checking in with yourself.

Whether it’s stepping outside for fresh air or finding a quiet corner for a moment to breathe, don’t underestimate the power of small breaks.

If staying overnight, bring comforting items like a book or playlist to unwind.

Self-care also means knowing when to say no—don’t overextend yourself for anyone’s expectations.

Finding Joy in Being Single

The holidays are an excellent time to celebrate where you are in life—single, dating, or otherwise.

Celebrating Independence

Being single means ultimate flexibility. You control your decisions, your time, and how you enjoy the season.

Want to binge a feel-good movie marathon? Go for it. Interested in splurging on a gift for yourself? You deserve it.

Embrace your freedom during the holidays rather than feeling pressured by societal norms.

Creating Your Own Traditions

Instead of focusing on what you don’t have, create traditions that celebrate you.

Cook your favorite festive meal, decorate your space exactly how you want, or host a “Friendsmas” with other singles.

These personalized traditions can make the holiday season feel refreshing and rewarding.

When to Seek Support

If holiday stress feels overwhelming, seeking support can help.

Building a Support Network

Friends and like-minded communities can offer a buffer. Some friends may also struggle with similar family conversations, so lean on each other.

Plan outings or virtual catch-ups between holiday gatherings to decompress and share laughs.

Professional Help

If the pressure and comments about your singlehood feel too heavy, consider speaking with a therapist. They can provide tools to manage stress, set boundaries, or respond to tough conversations.

Find Your Joy!

The holidays aren’t just about family traditions—they’re a reminder to find joy, regardless of your relationship status.

By preparing responses, shifting the focus, and embracing your independence, you can transform uncomfortable moments into opportunities for self-assurance.

Stay confident, surround yourself with supportive people, and enjoy the season exactly as you are: whole, complete, and thriving.

The *Ultimate* Dates & Mates Holiday Gift Guide

THE BEST HOLIDAY GIFT GUIDE

Some people have a hard time shopping for their significant others during the holiday season. The pressure is on during this crucial time in a relationship. So… this year we’re gifting you with a list of our FAVORITE gift ideas for every occasion.

 

A first rule of thumb: Emotional value always trumps monetary value.  

Get them something that shows you’ve been listening rather than something that shows you waited until the last minute and just plunked down a wad of cash instead of taking the time to choose something that your significant other would specifically want.

I’ve put together this holiday gift guide to help you think through your options if you want to make this holiday special. I’ve made it super easy for you: 

You can either read through my extensive guide to picking the perfect holiday gift OR scroll down to the bottom for my cheat sheet gift guide.

IF YOU WANT TO GET BROKEN UP WITH… 

A one-way ticket to relationship discord is a bad gift. This can be anything from a flat out thoughtless gift, to misconstrued presents, to showing up empty-handed.

Here are a few things to stay away from:

Electronics

From iPods to Kindles to a new microwave, if it’s got a warranty it’s an appliance—not a sign of affection. Anything that plugs in, takes batteries or is powered by the sun, no matter how cool you may think it is will be too impersonal for the first gift-giving exchange in a new relationship.

Jewelry

Dating is not the same as marriage, and even the rules of giving back the ring after divorce are muddy so why get caught up in the big expense of something that may or may not last in the long run? Or even worse, cheap jewelry will just look like you don’t care. 

Diamonds are forever, but a new relationship may not be. Wait until a meaningful anniversary to give something shiny.

Clothing

Unless you’re a successful clothing designer, you’re still learning the style AND SIZE of your new mate. Instead of risking a huge fight about the difference between a petite small and a small small, opt for something a little more tailored to their taste than to their waist.

Novelty Items

Even if Spencer’s Gifts does see a huge influx of customers during the holidays, you don’t have to be one of them. A black-light poster, Snuggie or lava lamp (see No.1) may be cool in your crib, but anything that elicits a laugh may not be quite the reaction you were hoping for.

Sexy Anything

Lingerie, silk boxers, and (heaven forbid) sex toys can and will send the wrong message. Especially when your lady’s friends ask her what she received for the holidays. Save the kinky stuff until you make it to Valentine’s Day.

Nothing

Showing up empty-handed is even worse than showing up with a dildo. Even if you’re two weeks into a relationship, giving something is always better than nothing. So if you’re stumped on what to get and are only coming up with items from this list, at least make sure it’s something, not nothing.

Cards

And I don’t mean playing cards either (which would also make a terrible gift). While the simple act of giving a card is better than the dump-worthy gift of nothing, it’s still not enough. If you have to give a card, make one yourself. Make it meaningful with photos or showcase your artistic side. Rule of thumb: If someone else is quoted is on the card, choose again.

Gift Certificates

Practical, necessary and sometimes thoughtful, gift certificates can be a great gift for co-workers, employees and handymen. For anyone you sleep next to, not so much. If you know where they like to shop get them something from there with a gift receipt, not a blank check to take time out of their day to buy themselves a gift. 

Home Furnishings

Because nothing says “I don’t want to see you anymore” like the gift of a fleece blanket.

Lotion or Soap

Do not be tempted by the Bed, Bath, and Beyond gift basket. Even though the sales lady says women always love it, chances are she already received several from people who don’t really give a crap about her. Try to be the exception.

Also, if someone were to give you the gift of soap, wouldn’t your first thought be, “oh my god, do I smell bad?” Definitely stay away from soap.

Money

You laugh, but it’s been done. Aside from being kind of totally rude, it shows no originality, no emotion and is really, really lame. If you’re so out of your element that you are thinking about resorting to giving the gift of green, it may be time to get some professional help.

BEFORE YOU PICK OUT A GIFT (NOTE: GUYS DEF READ THIS)

Talk and Listen

Many times women think they are dropping hints about what they want for months and weeks before the holiday. Often times men are completely oblivious to these hints.  If you think you may have missed the message, simply try asking what she wants. 

Even if it’s direct, it will show her that you care about her and want to get her something she would like.

What they want most is YOU

Spending quality time with you is one of the most valuable things you can give your lady. Take a moment this holiday season to treat her like the queen she is. Take the reigns in the kitchen and cook for her tonight. Offer a foot massage at the end of a long day. These gestures will mean more than anything that comes in a box.

Let’s not forget the JEWISH HOLIDAYS

If your family is anything like mine, you are planning for Christmas AND Jewish Holidays. It’s always appreciated if you do something to acknowledge every night of Hanukkah, but usually not expected. You have the opportunity to be clever though and build each gift upon the last.  Perhaps you order candy hearts made that spell out a special message across the eight nights. Or give her some chocolate Hanukkah gelt nightly and then give her a guide illustrating how the number of coins corresponds to different gifts of her choice on the eighth evening. You can give her a variety of options and let her decide how she wants to spend her gelt. That will give you points for being cute and creative but also ensure that she gets exactly what she wants.

OKAY NOW HERE’S YOUR CHEAT SHEET!

FOR THE NEW BOO

Regardless of how far along you are in your relationship, from benign dating to almost boyfriend/girlfriend status – get them something for Hanukkah or Christmas. 

You don’t have to overthink this gift and you should probably not spend a lot of money. However, all relationships – even new ones – do warrant some sort of acknowledgment this season.

Here are a few ideas to get you started or spark some inspiration:

Remember that what they want most is to spend time with you. Try giving the gift of an experience!

Groupon has everything from painting classes to concerts to kayaking trips.

Are they obsessed with music? Try a stylish crate for their record collection.

Have they ever mentioned wanting to make time to read more? Try gifting an Audible Membership.

 

FOR YOUR LONG TIME BAE

Sometimes partners can feel taken for granted after a few months or years so this is your time to remind her how special they are to you. 

Again, try the gift of an experience! Do something new to get you out of your routine.

Most ladies love jewelry so if you’re not ready to pop the question (which I don’t usually recommend doing during the holidays) try a lovely necklace instead. The box MUST NOT be misleading to her. There’s nothing worse than thinking you’re getting an engagement ring and ending up with a pair of earrings.

For a guy, try a nice watch. A good watch is a timeless gift. There’s something for every price point.

Whatever you do this season, it’s a good idea to talk about how you like to spend the holidays in advance to make sure you’re on the same page.

And don’t forget to ask them out for New Year’s Eve. There’s a superstition that you’re doing on NYE alludes to what you’ll be doing the rest of your year. So make sure that this New Year’s, the fireworks aren’t only in the sky.

 

 

Surviving The Holidays While Single

A Few Dating Dangers For Singles To Avoid This Holiday Season

Navigating the holidays can be hard when your parents keep asking why you’re still single. Top it all off with dating app fatigue, and Millennials & Gen Zers are ditching dating apps more than ever. But mostly, holiday dating app fatigue comes around due in large part to awkward questions from relatives.

How many times have you heard something on the order of, “Why are you still single” or “when are you going to settle down?” Be prepared for all of the awkward questions because you’re going to get them. 

If you don’t want to talk about why you’re single during the holidays, share all the accomplishments that you want to share instead of focusing on the negative. If all else fails and they just keep asking, tell them some of your bad date stories.

Here are a few tips on handling awkward conversations with relatives:

1. Stay optimistic about dating apps.

Dating apps are the most powerful tool in your dating tool box. If you’re feeling down about dating apps just remember this:

Now more than ever daters are finding love online. But regardless of this shift, people do tend to get down on dating apps around the holidays. Often parents and relatives don’t understand that online dating is the norm now. The latest news may not have helped that…

2. Tell your parents the dating apps aren’t dangerous.

You may have seen in the news that the safety of some of the best dating apps has been called into question. A recent investigation proved that registered sex offenders are finding victims through free dating apps and websites such as Tinder, OkCupid, Plenty of Fish, and more. 

This is terrifying. But, it’s also an opportunity to examine 1) which dating apps you are using and 2) how we are filtering potential dates

On episode #287 Dates & Mates, Damona discussed this with Rene Lynch, editor of LA Affairs in the LA Times. They break down this controversy: 

  • If you’re concerned about your safety, certain dating apps automatically use background checks against the sex offender registry – like Match. These are typically paid subscription dating apps that have the resources to filter for dangerous situations.
  • Do some research on your own! Before you meet your date in person:
    • Schedule a pre-date phone call or video chat & make sure that everything checks out.
    • A quick search on all social media platforms can tell you all you need to know about your match.
    • If something feels off to you, follow your intuition.

3. Think about dedicating some extra time to dating.

Damona always encourages daters to be proactive in finding love. And since we’re all on holiday, let’s take advantage of all the free time! A good rule of thumb is to dedicate five hours a week or more to your dating process.

4. If you’re experiencing dating app fatigue, take a break!

We have all been there. Sometimes you get tired of the seemingly endless and monotonous game of swiping. But once you take a step back, you realize that the dating apps are more than just swiping at faces. 

If you’re in a dating rut, make sure you take some time to regroup. As Damona says, it’s better to take a break than to bring the wrong energy into dating.

5. Revisit making IRL connections.

While you’re taking a break from dating apps, make an effort to meet people in real life and be more conscious about the kind of person you are looking for. You can actively search in relevant spaces where you can find potential matches with common interests. 

6. Where’s your match hiding?

If you’re looking for someone that has a professional career, you might want to go downtown at happy hour and chat up the people that work in those office buildings. Or if you’re looking for someone who has a big heart, try attending a charity event and places with people who make philanthropy a part of their lifestyle.

Do you have a dating resolution for next year? Reach out to us on socials (@DamonaHoffman on all platforms). Happy dating!