The SharpMan’s Guide to Dating a Single Mom

Submitted by SharpMan Editorial Team on Thursday 14th October 2010
In this article
  • Why dating a mom is different.
  • Tips to impress her.
  • What NOT to do.

With more than 11 million single parents (at least half of whom must be women) in America today, there is a good chance that at some point you may meet a sexy single mom and, if you are lucky, land a date.

What Do We Mean By "Dating?"

What do we mean when we say the word "dating"? You first meet someone, maybe through a glance at a party and some casual flirting. We all have experienced that introduction where you think, "Yikes, she’s hot!" Then maybe you take her to dinner and a movie, and perhaps some dancing. (But if you do, you haven’t read The Case Against Dinner and a Movie.) If things work out, you have the first kiss, and then: the first "overnight."

Things may progress, and you have a first weekend trip together. Then, as you get to know her a little more, you learn her idiosyncrasies. You become more comfortable, less cautious, more willing to share your feelings, yourself, and maybe you even learn new things about yourself. You could develop a routine with the person, and particularly discover the kinds of things about which you are going to have to compromise. That is dating.

The Difference Between Dating a Single Mom and a Non-mom

Understanding the difference between a single mom and a single non-mom is key. A mom cannot be as carefree, flexible, free-spending, spontaneous or risk-taking as a non-mom. While you may find a single mom at the most hip, happening nightclub in your greater metropolitan area, dressed to kill in thigh-high black leather boots and a mini-skirt the size of a postage stamp, that’s only because she spent the previous 48 hours making arrangements that enabled her to leave the Planet of Motherhood.

With all of that in mind, check out a few specific tips on how to treat that hot single mom in a way that will have her begging for more:

Making It Work With a Single Mom

Be understanding about where she’s coming from. For most single moms, dating and sex after having kids is stressful. The needs of her children define her boundaries. Understand that she is juggling roles, tasks and emotions that are different from those of a non-mom.

A mom needs to be available to her kids. This often means lack of "alone time," little-to-no parental relief and balancing the demands of family, career, economics and dating. Understanding all of this is the first step to success in dating a single mom.

Be understanding of her need for flexibility. Understand that spontaneity and motherhood do not always mix. A single mother is not necessarily carefree and may not be able to make spur-of-the-moment plans. Surprise outings may seem romantic and fun, but are difficult for most single moms to manage. Just when she thinks plans are set, there are many reasons why she may need to cancel, change plans or reschedule.

For example, she may need to help her kid with homework or any number of extracurricular activities (i.e. a talent show, a science project, dance class or baseball practice) and she may not know about them until the last minute. Be flexible and ready for an extreme change of pace when necessary.

Be understanding about how expensive it is to be a single mom. A single mom may not have a lot of money and often has a budget to which she needs to stick. One of the biggest expenses a single mom with a young child has is babysitting. Keep this in mind when planning dates or extending invitations. While your hot momma may want to see you often, she may only be able to pay for a babysitter once a week.

SharpMan Tip: With this in mind, consider that one way to see her more often is to offer to pay for the occasional babysitter.

As an alternative, consider planning activities or outings that may not require a babysitter. For example, if your hot momma shares custody with an ex-husband or other family members, coordinate a date on the weekends when her kids are away.

On the other hand, if you have already met them, plan an at-home movie night or an outing with age-appropriate kids’ activities that everyone can enjoy. Although this will take more coordinating on her part, she’ll appreciate it and you’ll score some major points.

Be understanding about the boundaries of your involvement with the kids. If your single mom of choice does not want you to meet her kids immediately, be patient. Don’t take it personally or assume that she does not like you enough to introduce you to her kids. She may want to get to know you and give you the opportunity to get to know her as an individual and a woman before you meet her kids and see her "mom role." In addition, she may not want the kids to meet every man she goes out with and wants to wait to see how your relationship develops.

Follow her lead about dos and don’ts in front of the kids. Accept her boundaries about how much affection to express in front of the kids, and at what pace. Talk with her about the comfort level of all involved and proceed with caution. And let her do all of the disciplining. If you have an issue with the kids’ behavior, discuss it with her when the kids are not around. As a rule, do not try to be a father or a father figure to her kids, particularly in the beginning. They may end up resenting you.

Be open to her need to include the kids.

After you’ve been dating for a while and you both feel there could be a long-term relationship in the works, be open to her bringing the kids on some of your outings. If the kids come along, then be playful, light and fun. Do not take it personally if her kids act as if they dislike you, decline to participate in any activities with you or express jealousy. Just hang tight. They will likely see what she sees in you, and come around eventually.

Do not get in between her and her ex. Dealing with her kids’ dad can be tricky. Let her handle all the communication/miscommunication and/or primary interaction with him. Listen when she wants to talk about him, but do not ask probing questions. The break-up may have been a difficult one and it may be difficult for her to talk about it. Hostility or bad-mouthing will not win you any points. Extend common courtesies whenever possible, but know your boundaries.

Armed with these SharpDating guidelines, get out there and woo!

This article last updated on Thursday 14th October 2010
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