Pressing Love Questions

by mssinglemama on December 12, 2008

Too urgent for a video, and I want your input.

Single Parent Dating Question #1

You know her as Tracy or Little Man’s Mom, she writes the blog A Brand New Day. I fell in love with Tracy the moment I discovered her blog because she has this spirit you can feel. Always light, airy and optimistic and she’s been a single mom for years.

If you follow her blog you know she’s found someone – very, very special. For the first time, circumstances surrounding weekend plans mean it’s time for a sleep over. Her son is 9-years-old and as she says, “he knows stuff.”

The Question: “Should he sleep in the guest bedroom or my own? And how do I explain it to him?

My two cents: Honesty, is always the best policy. Kids aren’t stupid and it’s okay for them to see their parents in healthy, adult relationships. But I know nothing of the Land of 9-year-olds. I’m still in Toddlerville where not much explaining is necessary. Mr. Man took off on a space ship by the way – to the moon. It’s a very happy place where Mr. Man still thinks of Benjamin fondly and he loves the story. I’m trying to laugh about it… in reality, Mr. Man is devastated.

Single Parent Dating Question #2

This one comes from a single dad to a 6-year-old girl. A single mom of four has caught his eye at their children’s school and well… read what he had to say (tell me this isn’t completely adorable):

She is always looking at me from across the school yard. When we get close to one another, we make direct eye contact, I mean eye contact, we will stare at each other for one or two seconds directly and say “Hi” or something silly to each other. Other times she is stand-offish, I am thinking she likes me and then she goes into reality mode.

I am not a whimp and I do have a backbone but I am a bit shy. I hold my eye contact with her to let her know I would or I could be there for the long haul if she wanted me. Its when she goes into reality check mode that scares the crap out me. That and rejection.

I am so afraid of asking a girl out. I have been in the Canadian Armed Forces, been overseas as a peace keeper, been in the Rocky mountains hunting Grizzly and yet I can not find the courage to ask a girl that I like out, I do not understand myself. I know I am not a coward or run at the first sign of trouble. Do you know why guys like me are like that? I know I’m not alone.

The Question: How do I make the first move and ask a single mom out? Am I the only man afraid to ask a woman out?

My two cents: Nope, Mr. Single Dad, you are not alone. I have only been asked out by men a handful of times. Ladies, take note, this is why I encourage all of you to ask them out yourselves. So what do you think? Does she like him (I think so)? And how should he break the ice, take it to the next level, and ask her out?

Thanks in advance for your fantastic comments, I know you’ll be able to help.

[Photo: Ingrid Bergman (my favorite) in Kiss of Death – 1947]

Related posts:

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  2. Single Moms and Love
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  4. Love at first sight.
  5. Love vs. Lust

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