I learn so much from your podcasts! I am 36 and recently separated from a 16-year relationship. After waiting eight months, I decided I was ready to start dating again. A few colleagues of mine recommended some dating apps, so I checked them out. I went on two OKCupid dates and they went horribly. Then I gave it one last shot and started talking to a guy six years older than me. We have been talking for two weeks but haven’t met in person yet. So far, our connection has been great!
So here’s my question for you: is there a certain timeline to meet this guy and move forward from there? What do you suggest when it comes to going from cyber- and phone-chatting to meeting IRL?
Laura in LA
I really love that you took time after your last relationship ended before jumping back in the game. You waited until you were totally ready to date again, something I always recommend to people going through a breakup. That way, you don’t end up trying to get over your last love by getting under someone new—a practice that is not only unfair to the rebound person, but also fails to mend a broken heart.
I also love that you didn’t give up after two lousy dates! So many people ditch the dating apps after being mismatched with a couple of duds, but there are tons of fish in the sea. You have to keep swimming to meet your match.
It seems like your perseverance may have already paid off. You’ve found someone who you have a connection with, but now it’s time to take that connection offline and into the real world.
I totally understand why you may want to delay meeting this guy in person. You’re still getting your feet wet after ending a long relationship, you’re relatively new to dating and pretty green when it comes to dating apps. But sometimes, for the right person, you have to step out of your comfort zone and take that chance.
It sounds like you’re really connecting over the phone, which is great. But even though you might feel like you know him, you don’t really know him. That’s why it’s so important to meet in person! Sometimes we get in our heads about who we think a potential lover is. We create stories and images to fill in the blanks, and end up with super high or unrealistic expectations which are immediately gutted when there’s no chemistry. So why waste time? The longer you wait, the more likely you are to feel let down by reality (because nothing can ever be as perfect as we make them in our heads).
The sweet spot for planning a date is between 2-3 week after the first message is exchanged. So if it’s not possible to meet up with someone right away (because of distance, etc.), I would say that two weeks of email- and phone-courtship is the absolute limit. Just meet him now: the sooner you do, the sooner you’ll know if it’s a good or bad fit. Whatever the result of the date, you can move forward with him or move on to someone else! Just keep swimming!
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