50 First Online Dates (And What I Learned)

Online dating is a mass opportunity and with it, comes losses and wins of equal measure. Sprinkle some crazy into that too.

Date 12- When a guy says he’ll come and meet with you when he’s four hours away, take CAUTION. Also, if that doesn’t make you think twice, his emotionally-charged and psychedelic messages will: “The tiles glistened under the bathroom light. I like doing push-ups. 375. But I need to watch my weight.” As I expected, he canceled and to my sweet relief.

Date 3- Location is everything. Someone picked to go ice-skating for the first date for a change. It also helped that he just came from work and was still wearing his uniform. Extra points for extra sexiness.

Date 47- Don’t tell me about your medical conditions on the first date. Yes, that includes, “I’m losing hair profusely” and “I have to use a cane sometimes when I walk for too long.”

Date 48- Online dating is also a quick way to get flings especially for the summer or weekend getaways. If you decide to fling, fling all the way! I once decided to meet a guy who clearly advertised he was in an open relationship aka polyamorous. LOADS OF FUN. No pressure and no expectations. I was doing a summer college program at the time, and we decided to play some ‘hooky’, play make-shift checkers, and go on a Grocery Giant Eagles picnic. The most fun I’ve ever had on a date. Period.

Date 15- It works in reverse too. Make sure to know a head of time if the guy you’ve been gushing over is not visiting your town temporarily. This can range from 4 weeks to 2 days! I once met a guy who said he had to leave suddenly for a family emergency in Iran when he originally intended to stay in the US for at least a month.

Date 9- Make sure to understand and read the things under Status/Orientation on profiles. Also, be vigilant because the terms “demisexual” “genderfluid” “open relationship” and “poly” really matter. I made the tragic mistake of dating someone for two months who I thought was perfect in every regard, too perfect, until I suddenly realized that ‘poly’ meant dating multiple people as opposed to admiring multiple people. Took me half a year to get over it…

Date 22- Was suppose to be. Don’t ask a girl for more pictures when she has put plenty already online. It comes off as really shallow. I blew off at least 3 guys for that same reason. Dare I say, it’s equivalent to me asking a guy for what position he holds in a company right off the bat.

Date 13- You are not your possessions. I once went on a date with someone who emphasized over and over again about his successful career endeavors- the grant he won, the classy friends he gained, or the car he just bought. I felt like I was in a commercial. Show me that your value as a person is multi-faceted. Now, THAT sells.

Date 25- Be wary of the location of your prospects. I didn’t have a successful date with someone, and the run-in at the bus-stop and pharmacy was not short of intense awkward.

Date 32- If you’re trying to impress a girl who’s a poet and you can’t identify who Edgar Allan Poe is, just DON’T. He tried writing me some couplets after only one date: “You were like a fairy, and it was so merry. I felt like such a fool ‘cause you made me drool.” Barf.

Date 29- Coffee shop. Perfect first date choice. My go-to for online dates. Can move to lunch/dinner if successful or to a quick scheduled appointment if not so successful. Finish the coffee and get moving!

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