But just because you were her age once, it doesn’t mean that dating a young woman is always plain sailing. Whatever the age gap, here’s how to date a younger women successfully. Youth might imply less experience, but it doesn’t mean a lack of empathy, nous and emotional intelligence.
And remember, it's kind of sexy when a man feels empowered enough to discuss his feelings.
If you don’t ask her out — no matter how innocuous or considerate the reason — she will assume you don’t want to see her. Leave the ask to the last minute, she has to scramble to find a sitter and that’s really uncool. This shows interest in one of the most important things in her life. Sounds cliche’, but I always appreciate it when a guy goes on about how much he adores his niece, or spends time with a friend’s baby. This isn’t necessary, and especially after you have been involved for a while you will likely sort out the who-pays-when conundrum. Which you may be – but if you ask too fast, she will know.
Plus, it tells her (and any other woman, for that matter) that she was your Plan B for the evening. But if you really want to see her, give her plenty of time to sort out her schedule. In fact, if you DON’T appear interested in her family she’ll think that you’re not into kids. When a guy laughs at my funny-kid story, or is sympathetic about my mom worries, I’m in. But if you tend to take turns picking up the bill, but she sometimes rearranges her life to get out of the house and pays for a babysitter so she can spend time with you, acknowledge that.“You look great for a mom.” That. But she wants to feel like you’re interested in her in every part of her womanhood — including motherhood. If it has been more than a few months, or things get very serious very quickly, and she hasn’t brought up introducing the kids, bring it up.
At the time, it felt so long but looking back I feel like it was the perfect amount of time. While it is hard to make the decisions such as how much time you want to invest in a relationship before things become official; it’s important to give it some thought.
With regards to my own situation, being together so long made the transition of mommy’s friend to mommy’s boyfriend to mommy’s fiancé to daddy (something she began doing on her own) to mommy’s husband much easier. Your past does not define you but it did help shape you and had a huge impact on the person you are today.
Further, if you’re not a kid person or don’t want kids, you should not date a woman with kids to see if you’ll change your mind.
I go out with single dads and childless men alike, and some of the latter admit (while others appear) to be uncertain about the logistics of dating single moms.
While the age of the child plays a factor, if you’re not looking for anything serious, you shouldn’t play the “I’ll figure it out” game with a ready-made family.
Don’t assume she’s not free when her kids are home. If you’re interested and want to see her, ask her out. They have a dad, regardless of whether he is in the picture, in the can, or in and out of the psych hospital. Of course you want to know when she is free, if she has the kids all the time and whether the dad is involved.
If she prefers not to go out when her kids are home, or doesn’t like to hire a babysitter on school nights, she’ll tell you. If you’re out and she is paying for a sitter it is really nice if you get the check. But if you explicitly ask these details on the first or second date you will appear reluctant about dating a woman with kids.
From salt-and-pepper George Clooneys to silver-fox Harrison Fords, young women are swooning over smooth older men more than ever.
These days the idea of young women dating older – often significantly older - men barely raises an eyebrow. A long stints in an asylum for the criminally insane? But just because she hasn’t shared a similar experience, don't feel that she wouldn't relate to your life or your issues; open up and you never know what wisdom she could offer.