Jumping back into the dating pool isn’t easy after you’ve been off the market for a while. You have the desire to meet someone new, but it seems like a lot of work. Where do you start? What do you say?
Dating can be fun, but it’s also highly stressful—especially if you’re the type of person that overthinks. To help you get over the initial anxiety (it’s totally normal, by the way, so cut yourself some slack), we’ve put together some tips and advice to get you back on your game.
First-Date Tips that Work
If you’re anxious about dating someone you don’t know, try this: psych yourself into thinking you are reconnecting with an old friend. Do you have someone in your life who’s just easy to be around? Imagine you are getting ready to meet with or talk to that person. Immediately, you will start to feel a sense of comfort and excitement, which will get you through those nervous moments.
People tend to share more easily and honestly about themselves if they feel safe and non-judged. Create a comfortable space by being kind, curious, and interested in learning more about the person.
Here are a few ideas to set the tone:
- Start with an ice breaker. You can say something basic, like “Tell me what you did this weekend?” or “What have you been up to this summer?” Starting with simple, non-personal questions like these will help both of you share about yourselves and establish a comfortable space. You’ll learn a lot about the other person simply by finding out how they spend their time.
- While they are sharing, search for a common connection/bonding point. For example, maybe they mention they like Thai food, and you do too. Something as simple as a shared love of exotic cuisine could become a segue into a conversation about travel. Have they been to Thailand? What are some of their most memorable travelling destinations, and why?
- Search for additional topics within the conversation. Be mindful; it should always be a two-way conversation. If it isn’t, don’t hesitate to jump in (if they are doing all the talking) or take a breather and let them speak (if it’s you).
If you feel the topic needs to change—for example, if they are talking a lot about work, and you want to learn more about them outside of work—don’t be afraid to steer the conversation into another direction. It doesn’t have to be abrupt or awkward; your words can actually beflattering and draw them in closer. You could say something like, “Wow, you sure sound accomplished. I love learning about your career success, but I would really like to learn more about who you are—tell me, what do you like to do when you are not working?” or maybe “You are so busy! Do you ever have any time for yourself? What do you like to do to blow off steam?”
First conversations are a bit of a balancing act, so be mindful that you are not asking too many questions. You don’t want to come across like you’re interrogating or interviewing them!
Pre-Date First Call Tips and Topic Ideas
Typically, a first call is more of an introduction, but it could lead to a more meaningful conversation if you are both open and have the time to speak.
- Find a quiet place to make your call. The best place to have a personal call is not a work environment. Find a place with minimal distractions. Don’t forget to keep your first call “cheat sheet” handy!
- Follow up. After the initial call, follow up with a text thanking them for their time and suggesting you speak again that week. By indicating your interest, you are leaving no guesswork.
- Don’t use texting to get to know someone. Texting is an excellent way to share your interest in another date, decline a date, say hello, or thankyou. Texting is not a good way to get to know someone, so avoid lengthy texting conversations in the early stages of a relationship.
- Talk on the phone a few times before meeting. If possible, try and have a few phone calls before arranging an in-person date. Here are a few topics you might want to approach over the phone:
- Career and accomplishments: “Tell me about what inspired you to choose your career?” Be mindful as the conversation can turn into work talk pretty quickly. After a few minutes of sharing, the conversation should change direction.
- Growing up years: “I’d like to learn more about you. What was it like growing up in your house? ”Open-ended questions like these will help you learn about their influences, family situation, religious involvement, and their values in general.
- Financial security: “So, where do you live in Toronto, what area?” or“ What do you like about your neighbourhood?”You certainly don’t want to be too blunt about finances, but there are plenty of ways to fill in the blanks without coming right out and asking. If you want to learn if they are a homeowner, for example, you can comment on how high real estate prices are and see what they say. Keep in mind, homeownership isn’t always an indication of someone’s financial situation. Some people are just not interested in investing in property as they might prefer to do that with a partner. You could also ask, “I’d like to learn more about your travel interests. Tell me about the kinds of trips you like to go on!” this could also be a segue from the travel conversation.
- Physical fitness: “I like being active and like to do (insert your interests here), and I love doing things outdoors. What kind of activities do you enjoy?” Based on the answer, you might even talk about doing that thing (hiking, tennis, horseback riding, etc.) together sometime!
The lead-up to a first date isn’t easy for everyone. If you take the time to talk on the phone and get to know each other a little before you meet, you’ll feel much more comfortable when you finally do get together.
I hope these tips help! And if you’ve been wondering how a matchmaker can help your dating life, it only takes 15 minutes to find out. Book a call today to see if we’re a good fit.
