Saturday’s Memoirs: Adventures in Bad Online Dates – Are You Daddy?

By Thesinglemomsdatingdiary

In honor of Mother’s Day weekend, today’s post is about jugging dating and being a single mom. It can be very difficult to switch gears from driving the carpool, packing lunches and reducing fractions to going out on a date and feeling sexy. I’m the single mom of two teenage boys whose lives still require a lot of my attention and I’m not sure I always succeed at juggling everything.

My boys have had several years to get used to seeing me date, but I usually don’t introduce them to someone unless it’s pretty serious or has some potential to be. At first, my boys were grossed out by anyone thinking their mom was attractive and just couldn’t stomach the thought of it. I can remember when my son was much younger, maybe 12 he saw a man checking me out. We were at a traffic light and a trucker was obnoxiously looking me over. My son said, “Ew he’s checking YOU out.” Taking the liberty to translate this for you to 12 year old boy it means: “Gross, you’re not hot. You’re my mom!” Sadly, this is one of the first moments that would undoubtedly scar my son for life.

That was several years ago and now they both have adjusted. However, the first few weeks of dating someone new requires a lot of finesse until I decide if he is someone I want to introduce to the boys.

Last summer I had been out on a couple of dates with someone I met online. We’d only been out twice and we were having a hard time finding time to spend together, between my two kids and his five kids. Repeat, his five kids.

One summer evening and my boys decided at the last minute to go grab wings and watch a football game. The game would take a few hours and luckily the man I was seeing had some free time too. After a few texts he was rushing over to spend some stolen moments with me. It was too early to know if we’d have long term potential, but we did like each other’s company and we had a lot in common. I was anxious to have him come over for the first time as this was a big step in knowing if we had any potential.

The excitement was building as I changed my clothes, fixed my hair and did a quick shave in the bathroom sink. When he arrived, we went down to my finished basement, turned on a movie and relaxed with some wine. It was romantic and this was our first time of really being alone. We started kissing and it got kind of heated, let’s just say. After only about a half hour, we heard muffled voices upstairs. Oh, snap the kids came home early and we were busted. There was no back exit, no way of sneaking him out unnoticed. We both weren’t ready for this situation.

We decided to cut our date short. He was completely freaking out about meeting the boys and unfortunately, there was no way to avoid the very awkward moment awaiting us. We walked upstairs where the boys were quietly waiting for us, a little too quietly waiting for us, I might add. Before I could make the proper introductions, the boys said with innocent and straight faces, “Are you our new Daddy”?

My date started nervously coughing and was obviously extremely rattled. My boys couldn’t contain their evil giggles and my handsome date made a fast dash to the front door — I didn’t hear from him for a couple of hours.

Hand to God, my boys saw there was a car in the driveway, figured out that this was the man I’d been talking about recently and prepared a witty comment just for the situation. I have to give it to them, they made us feel really awkward. I did eventually date him again and we did laugh about it, but it took a few days for the embarrassment to subside. Whew, the crazy life of dating and being a single mom!

About Jennifer

Jennifer Kelton

I have created this blog and social dating community to turn negative dating experiences into positive ones. In fact, it’s the exact opposite of what the name implies. It was my own life’s multiple combo plate of bad date experiences that inspired me to create this supportive community. In the midst of my own search […]

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