Valentine's Day Icebreakers For All — Skip the Small Talk (2024)

Valentine’s Day is often viewed as a holiday for the romantic pairings of the world - and typically, folks figure that any reflection and connection surrounding this day is reserved for romantic partners. But more and more, people without a romantic partner in their life are reclaiming the day: we’ve got Pal-entine’s Day, Gal-entine’s Day, Mezcal-entine’s Day… OK maybe this last one is a stretch, but hey - I’m not here to judge. My point is, Valentine’s Day can be a celebration of so many different types of love and relationships. So let’s remember that reflection, fun, and connection can be had by all - partnered, single, or none of the above.

If you do happen to celebrate some rendition of the love holiday, you may want some non-awkward, fun ways to talk about it with others. Love and relationships happen to be two of the most vulnerable topics to discuss. Due to the sensitive nature of this day’s focus, we want to make sure questions and conversation starters are intentional, light, and mindful of peoples’ variety of experiences. No single-shaming, or any shaming of the sort here! Try these icebreakers and conversation-starters out at your (Insert Noun Of Choice) -entine’s Day celebration.

Use these for more relaxed settings in which you want to keep things light - think Zoom office holiday party, a V-Day gathering at your home, etc.)

1. If you could insert yourself into any romantic comedy, what would it be?

2. How would you plan a day that is completely devoted to pampering yourself?

3. We all know Cupid’s arrow makes you fall in love. If you had an arrow that could make anyone feel or do anything (within reason and with their predetermined consent), what would it be? Who would you point that arrow at?

4. What is one addition you would make to the five love languages? (Silly or serious!)

5. Marry, Kiss, Kill: candy! (Ex: Marry, Kiss, Kill: Twix, Take 5 bars, gummy bears)

Use these for more intimate, reflective, or extended conversations about love and relationships.

1. What is your favorite depiction of a romantic relationship or friendship in a movie, book, or TV show? What do you appreciate or admire about the way the relationship was portrayed? Does that have any impact on what you look for in your relationships, or how you carry yourself in relationships?

2. What is something that you used to look for in romantic relationships or friendships that you no longer look for? Alternatively, what is something you didn’t used to look for that is a priority to you now? What prompted this shift?

3. What do you think is your greatest strength in your relationships? In other words, what is something you bring to the table in relationships that you are most proud of?

4. What questions about relationships, love, intimacy, etc. are you grappling with right now, in the stage of life you’re in? (Note: there is a lot of shame in our culture surrounding experiences related to love and sex. This question is a great way to invite you and your loved ones to share what you still don’t know without fear of judgment.)

5. In what ways do your close relationships serve you - what do you feel you most receive from them? What do you feel you receive from yourself (or another force like nature, a spiritual being, etc.) that you can’t from relationships?