The other day, my grandma looked me earnestly in the face and said, “You will find someone when the timing is right. It hasn’t happened yet because you’re waiting for the BEST. I understand. It’ll happen, so don’t worry.” This came with no prompting from me. We hadn’t even been talking about it, but she could tell that it’s always on my mind.

Every moment in life, including time spent with grandmas, is a chance to learn something new. Dating should have its own classroom. A few friends and I put together a list of the things we’ve lived and learned in singledom:

Ashley

• Many times nice guys DO finish last in girls’ minds. But why? Aren’t they the ones we want to marry? Really interesting article on this here.

• Free online dating sites typically don’t yield good results. Even if there is one nugget, it took 100 bad tries to find it. That’s a 1% chance of success. Not good odds. I know, I spent 2.5 years addicted to them.

• Dating in high school and college was as easy as getting an A in Home Ec class. Boys/men were everywhere. The real world now means nice looking men in suits with headphones in on the train. And many, many taken left ring fingers.

Nat’s response to this one: I do have the impression that attractive men are getting scarcer the older I get. I think it is due to a combination of factors: attractiveness is no longer defined as just “good looking and hot” as it was in my 20s. Now, guys have to be good looking, hot AND smart(!), accomplished, well-travelled, good with kids, earning some money and so forth, hence, we want to find “the one” that will stay with us for the rest of our lives…

Nat

• Long work hours and colleagues that are all married or in relationships.

• Along with the first one, even my friends nowadays are 80-90% married or are in relationships, and this trend will not get any better the older I get! Unless people divorce in their 40s…but that’s kinda sad.

• In general, I feel like I have less time to relax, sit in a cafe, flirt, and just be. And if you are not in the moment and open, your dream boy can be sitting next you and you won’t even see him.

Debbie

• Being okay marrying a guy who already has kids. Or being told that there is a high likelihood that your future husband will already have kids at our age…I have some friends that are very much NOT okay with it.

• How to tell the difference between:

1. liking someone because you like them as a person and enjoy their company
2. liking someone because they treat you really well and you have fun with them and everyone else likes them
3. liking someone because you have all the same interests
4. actually liking them enough to want to potentially love them

• To remain friends or NOT after a short/long relationship. Do you have to consider if you were friends beforehand. Do you have mutual friends? Is it healthier to just go cold turkey?

• Dating one guy at a time vs. dating more than one at a time. [My take on this]

• Seeing an ex when you haven’t spoken in ages. What if he wants to go grab coffee? At what depth do you have to answer his questions about family/life/etc when he is no longer in your secret circle of trust…but used to be?

• Dating a guy you know your family probably will not like (at least maybe not at first). Do you introduce them or is it a deal-breaker and you need your family’s approval?

• How fast is too fast? The shock of finding out a super long ago ex is engaged after just talking to you three months before and was perfectly single. Obviously he was on the marriage path…

• Finding out an ex just got engaged. We know they weren’t right for us…but is it more just about knowing he is “ahead” in the game of life?

Clearly, us ladies have gone through a lot and probably will continue to live and learn in this harsh, cold, and tricky world of dating. The one concession to this is at least we have each other with whom to commiserate.