If you’re dating in your 30s, 40s, 50s, and beyond, you’ll likely end up online at some point.
Source: Unsplash
It’s awkward to put yourself out there on dating apps and on the internet in general, but it doesn’t have to be. If you want to connect with someone genuinely and without coming off as boring, creepy, or too intense, here are a few pointers that might be able to help.
1. This post of yours reminded me of…
Source: Unsplash Mentioning a specific post or story they shared is a great way to show you’re paying attention and genuinely interested in what they have to say. Maybe their beach photo reminded you of a hilarious childhood memory, or their book recommendation sparked a debate you had with a friend. Sharing that connection can create a natural starting point for a conversation and show that you’re not just sending out a mass message.
2. I loved your take on [topic], what are your thoughts on [related topic]?
Engage with their opinions and ideas. If they posted about a current event, ask them their thoughts on a related issue. If they shared a book review, ask for other recommendations in the same genre. This shows you value their perspectives and want to hear more about their interests. It also opens the door for a deeper conversation beyond just surface-level pleasantries.
3. I’ve been wanting to try [activity they mentioned], any tips for a beginner?
Show interest in their hobbies and passions. If they mentioned trying a new recipe, ask for their favourite cooking tips. If they’re into rock climbing, ask about their favourite routes or gear recommendations. This shows you’re not just scrolling through their feed aimlessly, but that you’re trying to find ways to connect with them on a personal level.
4. That [meme/video] you shared was hilarious, did you see this one?
Source: Unsplash Sharing a funny meme or video that relates to their interests is a playful way to break the ice. Humour is a universal language, as they say, and laughing together can create an instant bond. Just make sure it’s something they’ll actually find funny and that it’s not offensive or inappropriate.
5. I noticed you’re also a fan of [band/artist/show], what’s your favourite song/episode?
Source: Unsplash Finding common ground is a great way to start a conversation. If you share a mutual interest, it gives you something to talk about right off the bat. This could be anything from a favourite band to a shared love of hiking. Sharing your own preferences and asking for theirs can lead to a fun and engaging exchange.
6. I’m curious to hear more about your experience with [project/job/hobby].
Source: Unsplash Show genuine interest in their accomplishments and experiences. If they mentioned working on an exciting project, ask them about the challenges they faced and the lessons they learned. If they shared a photo from a recent trip, ask them about their favourite moments or hidden gems they discovered. This shows you’re not just interested in their surface-level achievements, but that you want to understand their journey and what makes them tick.
7. I saw you’re from [location], I’ve always wanted to visit! What are some must-see spots?
Source: Unsplash If you share a common location or have both lived in interesting places, use that as a starting point for conversation. Ask for recommendations on things to do, places to eat, or local hidden gems. This can lead to a lively discussion about travel, culture, and personal experiences.
8. That quote you shared really resonated with me. What’s the story behind it?
Source: Unsplash If they shared a quote that caught your eye, don’t just like it and move on. Ask them why it resonated with them, what it means to them, or where they found it. This can lead to a deeper conversation about their values, beliefs, and life experiences. It also shows that you’re not just skimming their content, but that you’re actually taking the time to engage with it on a meaningful level.
9. Your latest project looks amazing! I’m curious to know how you got started with it.
Source: Unsplash Complimenting someone on their work is a great way to show appreciation and spark a conversation. If they recently launched a new website, published a book, or started a new business, ask them about the process and the inspiration behind it. This can lead to a fascinating discussion about their passions, goals, and challenges. It also shows that you’re not just interested in them romantically, but that you admire their talents and accomplishments.
10. That [podcast/article] you shared was so thought-provoking. It really got me thinking about [topic].
Source: Unsplash Sharing your thoughts on a piece of content they shared is a great way to start a conversation and show that you’re intellectually curious. It can also lead to a deeper discussion about the topic at hand. If they shared a podcast episode about climate change, for example, you could ask them what actions they’re taking to reduce their carbon footprint. Or if they shared an article about the benefits of meditation, you could ask them how it’s impacted their life.
11. I love your sense of humour! Your [tweet/post] really made me laugh.
Source: Unsplash If they’re known for their witty remarks or funny posts, don’t be afraid to let them know you appreciate their humour. This can be a great way to break the ice and start a light conversation. You could share a funny story of your own, or ask them about their favourite comedians or comedy shows.
12. I’m also a big fan of [book/author/genre] that you mentioned. Have you read [specific book]?
Source: Unsplash If you share a common interest in books, use that as a starting point for conversation. Recommend a book you think they’d like, or ask for their opinion on a book you’ve recently read. This can lead to a lively discussion about literature, characters, and themes.
13. I noticed you’re interested in [cause/charity]. I also volunteer with [organisation], have you heard of them?
Source: Unsplash If you both care about the same cause or volunteer for similar organisations, use that as a way to connect. Share your experiences and ask about theirs. This can lead to a meaningful conversation about social issues, community involvement, and personal values.
14. I’m always looking for new music recommendations. What are you listening to these days?
Source: Unsplash Music is a universal language, and asking someone for their current playlist is a casual way to break the ice. You could share your own music taste or ask them about their favourite concerts or festivals. This can lead to a fun and engaging conversation about music genres, artists, and personal preferences.
15. I’m new to [city/town/neighbourhood], any recommendations for places to check out?
Source: Unsplash If you’re new to an area, or they’ve recently moved somewhere new, asking for local recommendations is a great way to start a conversation. It shows you’re interested in exploring your surroundings and open to new experiences. You could ask about their favourite restaurants, coffee shops, parks, or cultural attractions.
