Dating Tips for Single Moms (and other singles)


When I first started dating after my divorce, I realized dating was not as fun as I had imagined. I met my ex-husband Troy in college at 17, was engaged at 19 and married at 20. Teenagers don’t really date, they hang out. So I had never really experienced dating. Shoot, I didn’t know anyone who didn’t live in Northern Kentucky and Troy was the first person I had ever met who wasn’t raised Catholic. Yes, I was sheltered.

So here I am, 27-years-old with two kids (1 and 3) and I really had no idea what to expect when I started dating but thought it would be fun. I went out with a guy who worked at a store nearby my house, a few friends of friends and family, guys I had met while out at bars and even tried Internet dating. I quickly learned that it’s not that fun and you have to have rules… lots of rules. I would have never thought to ask guys certain questions before the initial date until these things started coming up. So in no particular order, here are some of the questions that must be asked.

  1. Do you have a valid driver’s license? I actually went out on three dates with a guy before realizing he did not have a license. We met initially through mutual friends at a bar so I left with my friend at the end of the night. As far as the dates, we had met out each time. It wasn’t until the third date that he told me he had a DUI and couldn’t drive.
  2. That brings me to number two. How many DUIs have you received? If they tell you they have a DUI, you might want to look it up. I discovered that guy actually had four DUIs.
  3. And that brings me to number 3. Are you facing criminal charges of any kind? While researching his DUIs, I found that he had criminal charges against him for assault. No, he had not told me this. Yeah, this guy was a winner!
  4. Do you do drugs? He might actually be honest.
  5. Are you an alcoholic? If they are going out drinking every night, they might not be the best or most loyal guy for you.
  6. Have you ever served jail time? Oh you would be amazed…
  7. If they have children: Do you pay your child support and see your kids? You probably don’t want to be with someone who doesn’t care about his own children.
  8. Are you racist? A friend of mine went on a blind date and the girl actually used the word “colored” to refer to an African-American like it was normal. That wasn’t the worst word she said.
  9. Are you actually divorced? Seems obvious, right? NO! You won’t believe how many men just got separated or PLAN on getting separated.
  10. Do you have a job and what is it? Court-ordered community service does not count!
  11. Do you live with your parents? There is nothing worse than a 40-year-old man who lives with mommy. Remember Failure to Launch? It doesn’t always end up with the happy couple duck taped to chairs.
  12. Do you own a car? I don’t care what kind of car it is but I hate to drive and I’m not letting their mommy drop us off at the movies.
  13. Are you okay with the fact that I have kids? Amazing how many guys will start a relationship and then decide they can’t handle that.

Once you have prescreened your date, you have to watch out for some other things. I had a guy ask me to lunch on a weekday for our first date. I met him at a nice local restaurant. He was a pilot, had two kids and seemed to have life in order. At lunch, he told me that he thought it was important to have sex on the first or second date to make sure the compatibility was there. I couldn’t believe he was so blunt.

 I had another guy ask me to meet him for the first time at the mall indoor play area with his kids. He said I could bring mine. I passed.

I was on my cell phone with one man who I had been on one date with. I mentioned I was in Meijer. He showed up there not even 10 minutes later just to say hi in person. CREEPY!

One guy told me after the third date that he wanted a serious commitment and saw us getting married in the near future. Actually, I have probably had something similar to that happen at least a half dozen times.

I work for a library and am pretty liberal. I met a guy on eHarmony and was very clear about both of these things. We had a very nice dinner and then walked over to the local bookstore. We passed a book about the Tea Party and I mentioned my frustration with this group (yes, I’m blunt). He immediately started telling me how he didn’t believe in the public school system (even though his children attended one), libraries or any other tax supported institution or program. Hey buddy, I work at a library!!! In fact, I am the public relations person for the library and am very passionate about my job. You knew this before you asked me out. Really, why waste my time? LOL

 I had been on about six dates with a guy who I really kind of liked. He called me from work one day and asked if I could check his private email for him because he was expecting something important and couldn’t check from work. I was hesitant but he insisted. He gave me his password. I couldn’t help but look at the email with the subject line “Hot Asian Women.” I thought for sure it was spam but discovered he belonged to several sites like this and um, they were pretty graphic.

One guy went back and forth from wanting to date to just wanting to be friends. Once I finally said I couldn’t be part of that, he confessed his love for me and told me what a “B” I was all in the same sentence.

I had a guy tell me on a first date that he wanted to find a woman to take care of his kids and didn’t care about anything else.

I had been dating this guy for a while when he took me to the Olive Garden. We had been waiting for a table for quite some time when they finally called for us. They were getting ready to seat us when he yells “no” and runs out of the restaurant. I noticed a girl nearby was laughing. I was so embarrassed. I walked out and asked him what was wrong. He said he dated that girl before and things didn’t end well. We went to another restaurant but it was just weird.

We all love a good laugh so what is the craziest thing that has ever happened to you on a date? What tips do you have for single women and men out there looking? I think I am ready to start dating again (not that guys are banging my door down or anything) but I need your tips and stories to make sure I avoid the crazies!

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18 thoughts on “Dating Tips for Single Moms (and other singles)

  1. I talked to a guy online for some time and finally decided to meet, he showed up at my door… now his online profile said 5’11 but this poor lil feller was maybe, maybe 5’5 WITH rolls of quarters in each shoe!! Now anyone that’s met me, knows im 5’8 barefoot… add 3-4 inch heels…. It looked like i was dating my child. OH, why cant people just be honest.. i would have at least worn flip flops!

  2. One time I went on a date and the guy reminded me of the WB singing frog! He was absolutely lying about everything!
    First of all he was 5’5, had a huge scare that wrapped around head (said he was hit by a train) and wouldn’t stop touching me! I thought I was being PUNKED!
    I felt sorry for him, so I sat with him for about an hour then tried to leave…he proceeded to follow me to my car and beg to come with me to meet up with my family. I agreed, but had to convince him to drive separate. I then proceeded to loose him and drove the entire 275 circle, just to make sure he wasn’t behind me!lol
    This was before cell phones! He called for about 3 days before he got the hint and stopped calling!
    Internet dating is a crap shoot!

    • Thanks for the comment Justin. You are right, not all men are dirt bags and there are definitely some crazy women out there too. Feel free to add your crazy stories. We all need to be able to laugh.

  3. When I was tending bar during college I had a guy who’d been in a couple of times during my shift ask me out. I was hesitant so I agreed to just meet him for a drink at a restaurant near by. Well apparently he got a pretty good head start and when I arrived, he was WASTED. So drunk that he tried to kiss me as I greeted him and then asked if I’d drive him home so we could have sex. All of this happened within about 10 minutes of me arriving. I left immediately. Horrible.

  4. Tried internet dating and one of the replies I got was from a woman talking about taking a long walk in the park and raking leaves into a pile so my daughters could jump and roll around in them as we watched enjoying the experience. My profile mentioned I had kids but not what they were and that was just a sample, this was her first email to me and it was 4 paragraphs long. Several women from out of town also contacted me to tell me they were coming to Cincinnati in the weeks ahead and wanted to know if I was interested in some fun. Yes there are plenty of crazy women out there too. BTW, yes I have a job, a car, no arrests or DUI’s, and I make my house payments. Oh and I’m really divorced. Good luck ladies. 🙂

  5. here is another question to ask perhaps before or durring the first date: if you could do it all over again/life that is what would you do differently? if he or she doesnt give you a load of bull but actually shares a part of thei humanity withyou. a second date might not be a bad idea. another question that you may want to use is: where do you serve others or how do you spend time making a difference and what do you do to make this world a better place? he/she may not be doing anything other than working really hard and trying to survive. nothing too wrong with that but people who are really thriving in life seem to be serving in some capacity.

  6. I am married and I am not looking, just ran across a post of yours and liked it.

    Today o try and remember the definition for insanity, is when you continue to do the thing and expect different results. You sound a little old fashion with good scrupulous, just don’t give in or compromise your basic self.

  7. A couple of these seem more sweet than creepy to me, but it’s all about your comfort level! My boyfriend gave his email to a few too many of those “Hot Asian Women” websites when he was single. They all go to spam now, and he keeps trying to click the unsubscribe thing on them and it doesn’t work. Hands down the grossest thing, though, is that his dad sends him porn. Straight up pornographic photos and videos. He’s done it since my boyfriend was a little boy. He’s asked him to stop but his dad always just ignores him!

  8. I guess some of these must depend on where you live… In many major cities, not having a car, or even a driver’s license, is really common and not considered at all weird. Where I live, even most drivers don’t want to drive downtown, because parking is exorbitantly expensive and you can get anywhere you need to go by public transit anyway. Most people in my circle of friends don’t have cars, and quite a few don’t drive – it would never occur to me to consider that any kind of an issue. But I expect it’s different in small towns and suburbs…

    • I never thought of that Miss Lynx. I live in Northern Kentucky, just 5 minutes south of Cincinnati. We don’t have public transportation options other than a public bus. No train, no subway… So the majority of people own cars. But my bigger issue was that he let me think he had a car and a license… when really he had so many DUIs that he had neither.

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