Conversation Hearts for Single People

In honor of Valentine’s Day and single adults ‘round the world: let us celebrate and laugh over the ridiculous conversations we’ve endured in our season of solitude.

Admittedly, I would love to be taken out for dinner on the most romantic Thursday of 2019. Preferably by an age-appropriate man who smells good and can hold an interesting conversation. But seeing as we are just days away from V-day and there are no suitors in sight I’ll choose to entertain myself and YOU with some of the oddest conversations I’ve experienced to date. In no particular order, here are my top 4:

1. By far, the most epically awful question I was ever asked… not once, but TWICE… was: “Does your baby have a daddy?” Mind you, this question was NOT asked by the same man or even in the same year. Nevertheless, I think I win in the game of least-romantic-pickup-lines. (Is getting hit on ever romantic?)

2. Don’t ask me how or why this is a thing, but if you want to do some online dating under the guise of a game simply download “Words With Friends” and start a game with literally ANYONE you aren’t friends with. WWF has a direct messaging component that seems to be quite popular with the fellas. They like to start a game just to slide into your DMs. My all-time favorite DM I ever got from a guy simply and eloquently said, “What you do?”

What.

You.

Do?

You can’t make this stuff up… it makes me giggle every single time. Side note: I crushed him in that match because your girl’s scrabble game is on point. Plus, I speak in full sentences, which tends to help. I was scared he was going to persist with the DMs so I came up with a response: “Me play game. Me no date you.” Luckily, I kept him distracted with my stellar vocabulary and I ended up not needing to respond to his inquiry.

3. Another time I was doing my usual Wednesday night thing: volunteering at church with our high school youth group. One of the boys waved me over to his seat during worship. I thought maybe he needed prayer or to tell me something deeply personal (he was sitting alone).

Me: “Hey bud, what’s up?”

Him: “Did you know I turned 18 last week?”

Me: “Really?! Happy birthday!”

Him: “Thanks. So… I’m 18 now.”

Me: …

Him: “So we can go out now...”

Y’all, it’s really hard to shock me. But I legitimately didn’t know what to say. I mean, everyone is raising their hands and singing Oceans while a kid in our youth group is casually hitting on me! Talk about keeping my eyes above the waves: my eyes were searching the room for a way out of that conversation! I obviously told him “No." (Several times.) When he persisted and asked, “Why not?!” my only response was, “Because you’re a fetus and this whole conversation is icky.”

4. Then there was the time a guy who asked me out THE DAY OF MY DIVORCE also asked my daughter out a few months later… in front of me. It was a very Gilmore Girls kind of moment and I was secretly very entertained by the whole thing. Well, not the WHOLE thing. I was a little miffed that I was so forgettable to him.

So there you have it. My top 4 most cringe-worthy pick-up lines. If you were given a box of conversation hearts this Valentine’s Day with comments you’ve heard: what would they say? No seriously, what would they say? I want to know! Share your most awkward pick-up lines with me as we wait for Friday, February 15th to hurry up and get here.