Dear Diary,


When I moved to the Cayman Islands, I told my father I wanted to run a marathon.  He laughed.  Not because he thought I couldn’t reach such a goal, but because he knew what it would take to cross the finish line.  In the past, he ran a half-marathon and clocked six or seven-minute miles during training.  Once he put a marathon into perspective for someone who never ran anywhere unless you count running late, I realized I should shoot for a 5 or 10K instead.  I downloaded motivational music onto my Ipod, strapped on a runner’s watch and tied up a pair of sneakers, which promised that I would burn more calories with every step than regular shoes.  Along the way, I had a couple coaches cheering me on and yelling for me to not pass out in the hot sun like I claimed I would do if I didn’t stop this nonsense immediately.  I never made it to the marathon–full or half–but I did improve my health, completed an 8-week session of boot camp, came in third in a workplace fitness competition and ran a mile in under 9 minutes.  Ok, maybe it was 9:30.  At any rate, I learned that I couldn’t wake up one day and run a marathon without the proper training.


The same is true for dating.  I’ve been out of the game for four years.  It was a wonderful break, but it didn’t turn into a marathon relationship or marriage. Now, I’m jumping back into the dating game–this time with a new member on my team…Baby C.  I’m a little rusty.   While talking to a really hot guy before going out to eat together, I mistakenly called my “ex” my “boyfriend” and then the guy asked if I was ready to date, since my daughter was only five months at the time.  I wasn’t, but didn’t tell him that.  When I got something from my car, I had to sift through a backseat of boxes from a mega toy sale. I don’t have to be a dating expert to know it was not a sexy look.  Now, that my little girl is almost one, I decided to enlist a coach.  Not just any coach, but Damon “The Champ” Young, Editor at, relationship guru and one half of the talented team at Very Smart Brothas.  I reached out to him for blogging advice but it quickly turned into me getting free words of wisdom on the guys I’m meeting as a new mommy.  It was a long talk, but it’s well worth your time!

Heather: Thank you for hanging out with us here at Diary of a First Time Mom. Let’s get right to it.  What advice would you give a new mom concerning dating?  Should she wait until her child is a certain age before she jumps back into the dating pool?


Damon: I’d advise any new mom to wait at least until her child is a year old before they start seriously dating again.  Sure, there will be times before that when you can go out and have fun, but (I’m assuming) the demands of being a mom — a new mom, at that — in the first year are going to be too time/energy/spirit consuming to put forth much of an effort with dating.  Also, new moms entering the dating game have to be cognizant of the fact that each man she decides to bring into her life will eventually have some type of interaction with the baby, and they need to ask themselves if the guy in question is the type of guy who could impact the baby’s life in a negative manner.


Heather: Good point.  I wanted to wait a year, because I was so focused on my daughter.  At the end of the day, I didn’t have enough energy in me to sustain someone else.  And I was still getting over her dad, who I did love dearly at one point in time.  That’s usually not the case for the child’s father.  He moves on quicker than the mother.  How can a woman get over her ex in order to heal and prepare for future relationships?


Damon: I believe that you only truly get over someone when you totally convince yourself that you don’t want to reconcile. If even a tiny part of you still holds on to the hope that things will eventually get back to how they were, you’ll stay stuck on the relationship, and stay checking his Facebook page and getting sore every time a woman comments on one of his picture. To heal you have to find a way to kill the hope.


Heather: Kill the hope. Well said. You also have to change your expectation and look at the guy as your child’s father not your man.  Sometimes men think single moms are looking for fathers for their children when often that isn’t the case at all. How should this be communicated?


Damon: Every time you go to a club or on a date, wear a baby tee with “I’m not looking for no damn father for my children” written on it.


Heather: Funny. Are you going to start selling those shirts for $5? Moms tend to look at their children as part of the package, but sometimes men look at kids as baggage. Do you think women lose or gain points when they become a mother?


Damon: There are exceptions — some guys don’t care, and some guys do prefer dating women with children — but, generally speaking, the more children a woman has, the more “points” she loses in regards to dating and desirability. I would never call a child “baggage,” but it is a reality that most single men (and most single women) would rather date someone who didn’t have kids.


Heather: Do any other communities have a dating game with a point system? B.C. (Before Baby C), I bought into this line of thinking. Then I realized, you’re not a higher quality person because you don’t have children. That doesn’t mean you’re not having sex. It just means you happened to not get pregnant. In your last answer, are you referring to single men with or without children?


Damon: I’m referring to most single men without children and majority (a smaller majority, but still a majority) of young (under 40) single men with children. (Yes, these men would be hypocrites, but that’s another topic for another day☺) Thing is, although having a kid is a deal-breaker for some men and some women, for most, it’s just one of the dozens of “things” that factor into how interested they might be in someone. A thing and not THE thing, if that makes any sense. Also, as shallow as a “point” system may be, everyone has their own way of accessing how interested in/attracted to someone they might be. The good thing about it, though, is that it’s a living and breathing scale. Things that may be looked at as negatives initially can be positives if you get to know/like a person, and vice versa.


Heather: Does the dating pool expand in a way for those who now have children and are more open to dating someone with kids as well?


Damon: Yes and no. I mean, if you’re a person (man or woman) who was hell-bent on not dating anyone with children, I don’t know if having a child yourself is going to automatically change that mindset. I guess it should, but people tend to be slow to change regarding things like that. At the same time, perhaps having a child helps you recognize the importance of certain qualities in a mate, and maybe this recognition helps you consider people you might not have before you had a child.


Heather: Ok, so once you’re dating, just how much information should a woman reveal about her child’s father? Should she avoid discussing her ex altogether when entering a new relationship?


Damon: I don’t think that’s a subject that can or should be avoided. Should the woman say things like “Well, Derrick used to call me Coffee Brown in the bedroom.” Probably not. But, the new guy will have some questions about your current relationship with your ex (and even questions about why you broke up). If this is a person you’re serious about, you should answer them.


Heather: When should a woman introduce the man she is dating to her child(ren)? Is it wise to bring the new man to family functions, such as birthday parties?


Damon: It would probably be better if she waited until she was convinced that the relationship was on a certain, long-term track.  Introducing the new guy to the kids before that is inappropriate, irresponsible and, frankly, dangerous. But, once a certain period of time has passed and trust is established, I don’t see the problem in bringing him to family functions. I’m sure her aunts and uncles will have a good time picking on him.


Heather:  My maternal grandparents were married 65 years and had 15 children together.  My uncles will definitely put fear in a man if need be….lol…So, what are the negatives of dating a single mom? What are the positives?


Damon: The two main negatives would be the knowledge that you’re always going to be second on the totem pole as well as the fact that there will probably always be another man in her life — a man she, at one point, (presumably) cared very deeply for. The main positive is that a guy may be able to see first hand what type of mother the single mom is. You don’t have to draw assumptions about her “mothering potential” the way you have to with a childless woman.


Heather: I can think of some more positives:)


Damon: I wouldn’t add any positives as much as I’d say that anything that was a good quality while she was childless still should be a good quality after she’s had the baby. I mean, if you were an awesome person/great catch before you had the child, you’re still going to be an awesome person/great catch afterwards. Yes, the baby changes things, but it doesn’t really change things that much.


Heather: Right! Sometimes people make you feel like now that you have a child you will have a harder time finding a man. I had just as many men approach me pregnant and later pushing a baby carriage as I did without children. A cute kid can be an icebreaker…lol. Speaking about that, some men are more attracted to women with children. Maybe they think we’re more nurturing, unselfish and perhaps even good cooks. How does having a child/children work to a woman’s advantage?


Damon: The things you mentioned definitely count.  Also, if you’re dating a guy who already has kids, perhaps he’ll look at your child/children and think “Whoa. If we get together, we can create our own AAU basketball team or group of tiny Avengers!” Whether he has kids or not, I’d advise any guy dating a single mom to be patient, considerate and, most importantly, treat her like a woman…not a “mother.”  Her having a kid doesn’t mean she still wouldn’t like to be approached, courted, respected and desired just like any other woman.


Heather: True!  What are some other misconceptions are about single moms?  I was worried about being seen as a stereotype when I am NOT a statistic.


Damon: When a woman has kids, I think many people (men and women) automatically assume that the woman ceases being a “person” and becomes a full-time “mother” whose every thought and action revolves around motherhood.  Basically, people think that a woman having a child means that they just won’t be interested in the same things, have the same personality or even be attracted to the same type of people. While I’m sure new parents do experience some slight personality alterations, if they liked Tarentino movies, traveling and T.I. before they had children, they’ll likely still like Tarentino, traveling and T.I. afterwards.


Heather: I still LOVE Tupac (who I think is still alive by the way:)  Before Baby C was born, I took trips to Thailand, Columbia, Jamaica and lots of places in between.  Now as a first time mom (who is back to my high school weight…woot woot!) I’m ready to break out my bathing suit and dust off my passport.  I adore spending time with my daughter, and now that she’s almost a year old, I realize it’s OK to want “me time” that doesn’t involve a baby gym or a children’s festival.  Will I still take Mommy & Me yoga?  Of course!  But I’ll also take a breather from the day-to-day stresses of single mommyhood.  And when mommy is happy, the whole house is happy!


Thanks again Damon for all of our conversations, which I couldn’t possibly include, which means you’ll have to come back to visit us again here at Diary of a FIrst Time Mom and perhaps some of our hot mommies will be featured on your new Very Smart Singles page.


If you want to hear more from Damon, you can virtually date him anytime by logging onto


If you enjoyed this article, check out Stuff Single Moms Say.  You may remember the viral video Damon and comedian Jason Russ put together called Sh!t Boujie Black Girls Say.  Well, Jason stopped by Diary of a First Time Mom and  put a smile on our faces.  Click here to read what he had to say.  

About The Author

Vlog Mom/DFTM Creator

Not long ago, Heather Hopson hosted a television show in the Cayman Islands. Today, she's back home writing a different kind of story as a new mom. In her 15 years working as a professional journalist, this by far is her best assignment! Growing up, she dreamed of becoming Oprah Winfrey. She was the features editor for her school’s newspaper and a teen talk show host for her city’s most popular radio station. She went on to earn a bachelor’s degree in Journalism from Michigan State University. After graduation, she worked as a television producer and reporter at CBS, NBC and Fox affiliates throughout the U.S. Instead of heading to Chicago to join Ms. Winfrey on her set, she bought a plane ticket to the Cayman Islands instead. She arrived five days before a category five hurricane! She lived in paradise for seven years, hosted an award-winning television show and traveled the globe with a government delegation. She also served on the Board of Directors for Big Sisters Big Brothers and spearheaded a Send a Kid to Camp Campaign. Then, she relocated to Washington, D.C. to obtain a teaching certification and instruct 8th grade reading at a high needs middle school. She later returned to her hometown of Pittsburgh, PA to raise her daughter Caitlynn, now 3-years-old. During her 10-month-stint as a stay-at-home mom, Caitlynn inspired her to create this blog, and Diary of a First Time Mom was born on Mother’s Day 2012. Two years later, she expanded the family to include 40+ writers. Currently, Heather serves as the communications director at Allies for Children. In addition, she is the owner of Motor Mouth Multimedia, which ranked #49 in Startup Nation’s Home-Based 100 Competition sponsored by Discover Card and Sam’s Club. Recently, The Pittsburgh Foundation and The Heinz Endowments selected Heather to receive an Emerging Black Artist award to develop Diary of a First Time Mom.