Dear Dating Mom: How to Dive In After a 10-Year Hiatus?

Dear Dating Mom:

I'm newly separated. I haven't dated in over 10 years. What's the best way to tackle it?



Dear Willing:

My gut instinct when I read a question like this is to tell you to turn out all the lights, curl up in a ball, and just sob. Then I realize, wait a minute, this isn’t me telling me what I should do, it’s about you. So, that being the case, my first suggestion would be take a look at what’s out there and THEN turn off the lights, curl up into a ball, and start sobbing. (Oh and don’t be surprised if you also develop a sudden urge to cut yourself.)


The dating scene is, well, let’s just say it isn’t pretty out there, I’m warning you. Just troll the dating sites and the screen names alone will give you the shivers. Don’t believe me? Allow me to introduce you to: “ManofLaMENSCHa,” “JewishPirate,” and "Big-Cog43," all looking to meet the love of their lives or least someone who will play with their pee-pee in exchange for a nice meal that they may or may not pay for.

Another thing to take into consideration is where you are at mentally. Before you do anything, you might want to find a good therapist. I say this because it’s always important to have that one person who isn't afraid to threaten to involuntarily commit you when you tell him you’re considering moving to Aimes, Iowa, where you will know no one, have no job, and will likely be the only Jew in THE STATE but are doing it anyway because hello? Did you not see how f***ing hot he is?

Now, this is not to say that you can’t get out there and go meet a guy for drinks or coffee. If you feel like testing the waters, by all means put on your bathing suit and get on out there! Even I’ll admit that every date isn’t horrible. I remember one night I went out with a guy that I couldn’t stop thinking was a dead ringer for Curious George (well, if Curious George was a spitter). Anyway, although I wasn't remotely attracted to the man, the conversation turned out to be pretty interesting

On the flip side, however, there have been many times I’ve walked in my front door so depressed and overcaffeinated that all I want to do is go and live out the rest of my life on an Alpaca farm.

Bottom line is, you don’t want to make the same mistake again, and although it might be difficult being alone after all these years, take it slow. At the very least, wait for the ink on your marital agreement to dry before you plan your next walk down the aisle.

Are you a single mom with a question about dating/sex/love? Or do you just want to try to trip Jessica up? Leave her a question in comments or you can write to her directly at

Image via Samantha Jo Campen

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