How To Date a Single Mother with Children

Boy kissing mom

There was a time when single mothers were a rare sight in society. Some were widowed, some sought divorces from abusive spouses, and some were abandoned. With the advent of 'starter marriages' and planned single parenthood, however, it is not unusual to meet an 18 year old single mother with two children. A woman in her thirties may be ending her third or fourth marriage. Eligible men today are often faced with the challenge of instant fatherhood in their mid-twenties. While there may not be the same social stigma attached to single motherhood as there once was, these women still face some significant challenges in the dating world.  If you've found a single mother that you want to date, I recommend you check out How to Attract Women before asking her out on that first date; single mothers often have high standards for their romantic partners and you want to be certain you make the grade!

For many single men without children or ex-wives, the revelation of single motherhood status can unfortunately become a romantic dealbreaker. Fears of a loss of independence or instant fatherhood responsibilities can come crashing down. There is also a financial concern, since instant families can have instant needs for support. This is assuming that a jealous ex-husband or boyfriend isn't lurking in the shadows, or a deadbeat father isn't living up to his responsibilities. Dating a single mother can be a challenge for even the most well-intentioned suitor, but it doesn't have to be impossible. Here are some tips for dating single mothers with children.

  1. Remember that you are dating the person, not the role. A woman wants to be noticed and appreciated for ALL of her qualities, not be judged by a role she didn't necessarily plan on playing. It's important early in the relationship to establish your interest in the fascinating, desirable young woman sitting with you on the couch, not the single mother who had to call three babysitters before the date. If you really want to explore a long-term relationship with this person, you must concentrate on a one-on-one level of intimacy first. There will always be time to meet her children and redefine your relationship later. Early on, it's about getting to know and trust the person she's always been.
  2. Accept the fact that her children's needs are a priority at times. She doesn't really want to cancel your date or take a raincheck on dinner, but she can't leave her sick child with an untrained babysitter. Single mothers often worry that all of their cancellations and postponements will be seen as a sign of disinterest in the romantic side of things. Be prepared for last-minute changes in plans or early departures due to an emergency at home. If she sees that you are flexible and understanding, she won't have to be so concerned about the occasional change in plans. Don't just pretend you understand what she's facing as a single parent -- actually put yourself in her position before becoming too disappointed.
  3. Don't be afraid to mention the 400 pound canaries in the living room. A single mother does have a past, and now a present and future with children. Talking about her ex-husband or father of the child shouldn't be seen as completely inappropriate. The trick is to discuss the things you really need to know and try not to bring up things you don't. You have a right to know if the ex-partner is still an active presence in her life, either as a custodial parent or friend or deranged stalker. Are there still some loose ends such as child support or finalized divorce papers to sign? You don't need to editorialize too heavily about an ex's personal shortcomings, however. She knows him better than you do and she may not be so impressed by your displays of bravado.
  4. Meet her children on her own terms and schedule. Put yourself in the shoes of the children for a moment. They've already lost a meaningful relationship with their own dad, and now mom wants to bring someone new into their home. This guy could be the nicest man in the world, but he's still a substitute, a step-dad. Children of single mothers may have a tremendous amount of anxiety about meeting mommy's new boyfriend. "Boyfriend" isn't a word in their vocabularies. Mommies don't have boyfriends -- they have Daddies who see them every day and live at their house. Allow her some time to sit with her older children and tell them all about how good you are to her and how much you want to meet them.
  5. Don't expect too much too soon from her children and extended family. It would be easy to become a big brother who does nothing but play catch and take kids to the arcade. It's easy to become the best fake Dad around. What's harder is to become someone worthy of the title. How are you going to handle discipline if a child misbehaves? What happens when you want to go on a date with Mommy and her child wants her to stay home? Sooner or later, you will meet her parents and siblings and other family members. Always remember that they have been through the same difficult transition period as your girlfriend. What they want to see most from you is true compassion and true intimacy, since they may have witnessed the opposite first-hand in the past.


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Great work, especially the advice on getting to know her children and giving them time.

By Kashy Ali