Passionate About the Westchester County Area
and the Moms Who Live Here

Sex and the Single Mom: I Should Have Seen the Signs

single mom

Attention World! I am no longer single. I am in a happy and committed relationship … at last. Which makes me wonder why I ever settled for less. So in an effort to help all the single ladies, these are all the signs I should have seen.

1. He Asks For Money

I’ve been the breadwinner in several relationships and one marriage. So I have a history with giving men money. Never in the early stages of a relationship, however. So when I was dating a guy for only a few weeks and he asked, I was taken aback.

He was charming and we wanted a lot of the same things. I saw the potential. Then he blew off a date and couldn’t be reached. I wondered what was up but didn’t want to seem too needy. So I only texted him like four times (too much?). The next day he called to let me know that his professor from college unexpectedly passed away and he went on a solo road trip to go to the funeral. So sweet, I thought. So, immediately I forgave him and we planned another date.

Later that day he called again. He said he had broken down on the highway and that all four tires were flat. He had a really nice car and a good job; so I was surprised when he asked in the next breath if I could wire him money for tires. He said he forgot his “main wallet” (is that even a thing?) at home and now was outside of DC with only cash and not enough for tires for his expensive car. I hesitated to send money. I’d seen enough Dr. Phil episodes to know this sounded fishy. But then I thought, what if he really is stranded? So, I offered to drive all the way to D.C. to pick him up instead. He declined and said he’d call me back when he figured all this out.

I regretted not offering him the money and began to worry that he was stranded. Then I got the following text, “I didn’t need the money, I just needed to know if you had it. I can’t date someone who’s broke and can’t even scrape together three figures. I don’t want to see you again. Don’t call me.” All worry and regret went out the window. What a joke. This brings me to my second sign:

2. You Feel You’re Being Tested

A few months before that guy, another date whom I’d been seeing for a while texted me a picture of a winning scratch-off lottery ticket. He asked, “Whoa, can you believe this!?”

I couldn’t. I thought it was great. I joked back, “Amazing, I guess you’re paying for dinner this weekend!” *insert smiley face, insert winky face, insert crying from laughter face.” He didn’t text back. A few hours later, I texted again, “What are you going to do with the money?”

“Well, I’m not spending it on you.”

I, of course, didn’t think this guy I was only dating and whom I split the bill with on at least two of our dates so far would be spending thousands of dollars on me. Although, I was hoping he would take me out some place nice that weekend. So a bit of guilt and a bit of shock caused me to respond with a, “Of course not. Where’s this coming from?”

He went on, in great length, to explain that he never won any lottery. Instead, he owned several businesses and needed to know what I would do with a large sum of money. Essentially, it was a gold digger test. And, apparently, I failed. Looking back there were other signs that he’d been testing me. He wanted me to come to a hotel where he was staying in the middle of a snowstorm, and I didn’t. Only to find out he was never there but just wanted to know if I’d come if he was. Ridiculous. But, I can’t deny that I too have a test for new partners. How often do you look at your cell phone during a date? 

3. You’re a Third Wheel to his Cell Phone

Social media is a part of any modern romance. In fact, Facebook is cited as evidence in one in three divorce cases these days. In a healthy relationship, no social media account will ever be more important than your partner. It took me some time to figure that out.

I dated a guy with a strong social media presence. He had Facebook and Instagram, as do I, and this new thing all my students were talking about at the time – Snapchat. His phone was always at his side on dates. He took pictures of our food, tagged our location, but didn’t tag or mention me. I understood why, I wasn’t ready for the world to know I was dating him yet either – we weren’t “there.” But, at times, it felt that his perfect picture or post was more important than if we were having a good time.

Some call this, faking it for the ‘gram.

He would go live on Snapchat and talk to the camera instead of talking to me. I decided that enough was enough and asked after a few dates if we could go on a cell phone free date. I mentioned that sometimes I felt like he was more interested in his phone and what others were doing than what we were. He denied the allegation and said he didn’t need his cell phone to have a good time. He took the challenge and we went to a bar agreeing to keep our cell phones away.

This man took more bathroom breaks than my grandmother after chugging a large iced tea. Clearly, he could not let the cell phone be and just be present. That was a deal breaker for me. I explained that to him after bathroom break number four. He seemed shocked and claimed he wasn’t using his phone. The crazy thing about social media though, it leaves a trace of your use. I didn’t need to check to be sure though, I had known it in my gut all along.

Which is what I am trying to get at with all these signs. In each case, I knew that these guys weren’t dating material. I don’t know if it was my desire to be in a relationship or my general self-doubt – but something made me ignore these clues. Don’t do the same!

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