10 Conversation Starters for Making New Friends After 40
1. Pay a compliment: Love their shoes? Their glasses? Lipstick? Purse? If so (please be genuine), just say it, and ask where they got it! That most likely will lead to a conversation about favorite stores online or off, deals, and expand into other hobbies or ways you each spend your time. From there, you can see if there is a connection you want to build on.
2. If you’re meeting the person through work, you can ask: “What did you think you were going to do for a living when you were a kid.” This is a fun way to bypass the “what do you do?” question that some people don’t like. It also taps into nostalgia which tends to put people at ease.
3. Another one for work: “If you weren’t at work right now, where would you be?”. This will open the door to either hobbies, which you might share, or family life, which you also might share.
4. If you’re meeting through a local social group you could ask: “What’s your favorite hidden gem around here?”. That could end up being a great place for the group to go next, and you start building a relationship based on shared interests.
5. If you’re meeting through an online group, presumably it’s built around shared interests or geographical location. Ask for recommendations or post your favorites, and ask if anyone wants to get together to discuss. For example, favorite books, movies, concerts, TV shows, museum exhibits. (Be safe, when meeting strangers, obviously).
6. If you’re out and about, besides the compliment conversation starter, you can ask: “Do you know this song? It sounds familiar but I can’t think of the name.”
7. Another one for pretty much any situation is, “Where did you grow up?”. This is another question that plays to nostalgia, which puts people at ease. The conversation might flow to what brought you both to your current towns and how long you’ve been here. Or you might discover you’re both from the same state or town, or they grew up in one of your favorite places to visit, which will carry the conversation to favorite hot-spots and memories of days gone by.
8. If you’re meeting around traditional vacation months such as Spring Break or Summer, you could ask, “What was your favorite travel destination?” Or “What’s the next trip you have planned?” Assuming, of course that you like to travel. If nothing else, you could discover some cool trip ideas.
9. Or, if near the end of the week you could ask, “Have anything fun planned this weekend?”. And if it’s the beginning of the week, “What was the most fun thing you did this past weekend?”.
10. And, if you’re struggling to keep the conversation going, because you’re feeling awkward, you can try, “I’d love to hear more…” or “What was the best part?”.
Keep in Mind
Admittedly, some of these may read a bit corny. Or like “pick-up lines”. Let’s call it. They are. And not all are right for every situation, you have to use your judgement. But here’s the thing, we connect with others over shared interests. This includes hobbies, shared lifestyles, our past likes and dislikes, similar experiences or backgrounds, and shared opinions. We also appreciate people who take interest in us, and people who offer solicited input, like book recommendations.
When in doubt, strike up conversation and look for what you have in common. And if you’re feeling awkward, you can even say it and make a joke of it. Like my now girlfriends and I did when we met through a local women’s group. “Who else feels awkward like you’re trying to date but for new friends.” Everyone raised their hands and laughed about it. Laughter creates a bond.