Readers: To read more on this topic check out: Dating in my 20s as a single mom?  or a personal account from Sabrina, “Dating as a single mother.” 

To read about cultural differences within relationships check out:

Why is he hiding our relationship from his family?

Cultural Differences Part 2: Am I being used? 

Dear Guys,

I’m a 24-year-old single mother of one child, and am interested in a guy who is in his late twenties, never married, and has no kids. I am currently a student intern where he is employed, so we have similar educational backgrounds and related professions. I will be finishing my internship soon, and would like to get a feel for whether or not he would be interested in getting to know each other after I am done. I’m concerned that he would be overwhelmed by the fact that I have a child. I’m not looking for a father-figure for my son necessarily since he has a great relationship with his biological father (we simply are not right for each other), but more so for companionship and someone to make sure that I take the time to have fun once in awhile. He seems to live kind of a bachelor lifestyle; however, in speaking to him it seems that this is because his life right now is able to afford him one. Do you have any good tips to see if he might be interested too? Also, what is your guy’s take on dating a single mom?
Thanks for your help!


Dear Rachel,

Thanks for writing. We’re sure there are plenty of other single moms, and dads, wondering the same things. We’ll just speak for THE GUYS here.

Hopefully this guy will decide to date you or not, based on who you are as a person, not the fact that you have a child. However, dating a woman with kids is not the first choice of most guys, especially guys who’ve never been married before, or who don’t have their own children. But each person is different, so nothing ventured nothing gained.

This guy is in his twenties, so he’s still a young man. He SHOULD be living the bachelor life because that’s what most guys in their twenties do, whether they have money or not. But this doesn’t mean he couldn’t fall for you, it just means he’ll be faced with a decision that he might not be ready to make. Does he really want to be a father figure right away? (It doesn’t matter that you aren’t looking for a daddy for your child. The fact is, you have a child, and whoever enters your life will have to embrace that to some degree in order to be with you.)

It sounds like you have a solid relationship with your ex which is great for your son. It’s also easier for a guy to walk into a situation that’s positive rather than dealing with a hostile and combative situation. We commend you for that.  But the truth is, having a child and an ex, could scare this guy away. (It would scare a lot of guys away.)

But many couples run into obstacles that are difficult. Religion. Ethnicity. Class. All of these have been known to create confusion and conflict. In fact anytime two people come from different backgrounds or have different experiences, there’s more of a chance of potential conflicts.

But even with potential issues out of the gate, this guy might not care. Here are a few reasons that guys in general might be open to dating a women with kids.

1. If a guy is super attracted to you he won’t care if you have a child. Or if he finds you fascinating.  Just make sure his intentions are true. Be careful.

2. If a guy has been married before. Or has a kid of his own. Now you both have similar experiences and the playing field is even.

3. If he’s just a cool guy who’s very secure with himself. This is a stretch for guys in their 20s but it’s possible. You’re more likely to find this with a slightly older guy in their 30s or 40s or older certainly. But it doesn’t hurt to explore all your options.

So that’s it in a nutshell. We hope we haven’t scared you off. If you’re into this guy, we say go for it. You’ve got nothing to lose really. But our biggest tip to you is be direct. Invite him over for dinner. If that scares him off, well he’s not the right guy for you anyway.

Hope this makes sense. Good luck and keep us posted.


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