photo 1 (2)


Welcome back to the Making the Online Dating Plunge series. Check back here for part one, which talks about making a profile and a little background about my experience with online dating. Today I’ll give some advice about what worked and didn’t work for me when it came to talking to people on OkCupid.


I got a lot of messages that only consisted of “Hey”, “Hey, what’s up?” or my favorite, “I like your freckles ;)”. I usually didn’t answer these (unless they were totally hot. Just kidding. Sort of). I was more inclined to start up a conversation with someone who asked a specific question (like: “Tell me more about your thesis.” SWOON) or showed some of their personality in their message. This is good advice for when you want to initiate a conversation, too. Mention something you thought was interesting on their profile and make it specific so the conversation isn’t too awkward. Make a joke, keep it light… Just go for it- what do you have to lose?

Once you start talking to someone, things definitely get fun. Here are a few tips for this stage in the online dating bizarro land:

1. Keep it light.

Same with your profile setup- keep things fun. If you go into this whole thing with the expectation of just having a good conversation with someone, then you will definitely have a good time.

2. Don’t message for too long.

It’s nice to get to know someone a little bit so you can get an idea of whether you would have fun for a few hours with them before you meet up. But let’s not get into Catfish territory. Eventually you want to meet the person to make sure you have chemistry.

3. You don’t have to message anyone you don’t want to.

Even if you’ve been messaging with someone for a little while, and they all of a sudden take a sharp turn into Creeptown, just stop messaging them. You don’t need to be polite. You don’t owe them anything. And you don’t need to reply to anyone who messages you that you’re not into. This is all for you, not them. Do whatever feels fun.

4. IMing on OkCupid can get weird.

They have this chat feature that can sometimes be fun, but can also be weird. Mostly weird. Just don’t be afraid to log off whenever you feel yucky. I’ve had people chat me and immediately ask to come over…to my sister’s house where I was staying. “Sure, just don’t wake the babies!” Ha. No thanks.

Thanks for listening to me rant again! If you’re still into perhaps meeting a special someone online, tune in for Part 3 coming soon. I’ll talk about the most fun part- the dates! Yay fun awkwardness.

Leave a Reply

Your email address will not be published. Required fields are marked *

Comment *