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]

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{ 8 comments… read them below or add one }

PT-LawMom December 12, 2008 at 7:56 pm

I love that you sent him to the moon. Great way to keep it light, lady. :)

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Frank December 12, 2008 at 8:56 pm

I would ask about something casual, like getting a cup of coffee together. Or, look for a lunch restaurant that is close to the school yard where you see her. Simply ask her if she wanted to get lunch sometime.

I had always been worried to ask someone out!

It’s not for everyone, but I like to make fun of myself, or use humor to open up the conversation to something more.

If that doesn’t help, I’ll show up in the park and say totally stupid things, so you look good. Then, just ask her out, so you can get away from me.

Something like that!

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SnowWrite December 12, 2008 at 9:26 pm

For Mr. Single Dad – Many of us women are very unsure of ourselves and the “reality check” could just be her thinking that she’s imagining your interest. Simple, be yourself and ask her out. Rejection is never easy but it’s a healthy part of living a vibrant life. So she says no, big deal. Swallow that pride of yours and do what could be the most important thing in your whole life, or not. Either way it doesn’t hurt to try!

For the mom unsure what to tell the 9 year old. All I can say is be flat out honest. At 9 years old (these days) kids know a lot more than we did at 9 (I have six kids of my own ages 12 yo to 23 yo). He doesn’t need to know details and most definitely set boundaries. It’s hard to date as a single mom especially as kids get attached very quickly. He doesn’t need to know details of course, but let him know you care about this person. Be careful though and watch for the revolving door effect. Kids are very observant and if you date many men and bring them home this is another issue altogether.

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Star December 12, 2008 at 10:46 pm

For Mr. Single Dad,
How about bringing her something…”read this article about kids our age and thought you might like to read it, finished this great book and thought you might like it, made too many X-Mas cookies and thought you might like some”…etc. That way you can test out the waters by letting her know that you were thinking of her but not putting any pressure on the situation and you’ll have something to talk about next time you see her. Good luck!

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LTP December 13, 2008 at 2:09 pm

Mr. Single Dad….as a single mom that has only had the courage to ask one man out since I’ve been on my own, I know it is hard….but I also know that I would be thrilled for a single dad to ask me out!! For me, I only want to date single dads…only a parent can truly get another parent (in my opinion). She’s probably just being cautious but I say go for it….you might be pleasantly surprised!!

The sleep-over: this is tricky but I agree with Alaina…kids know more than we give them credit for. The few times that my now ex-boyfriend stayed over when my boys were with me, we went to bed after they were in bed and we woke up before they were up…so it kind of solved itself. Good luck!

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O Solo Mama December 13, 2008 at 9:34 pm

Every time I think about leaving a comment for Tracy, I change my mind! But unless this is going to be a one-shot deal, I say stick to your own bedroom. Gotta move there one day. My daughter would be rolling her eyes and wouldn’t want to know anything. I suspect that’s where the 9-year-old who “knows stuff” is at too. Kids don’t care about your sex life as long as it doesn’t affect your relationship with them.

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Tyler January 29, 2009 at 11:28 am

I say go ahead and ask. I’m in a similar situation. We had the glances, we had some good conversation, she put me through a few simple tests. At first I hesitated because I too was affraid of rejection but eventually I asked her out for lunch, she said she’d love to… hopefully that’s where your story begins. Either way it’s worth it, single moms are the evolution of women, there’s the single women phase where they are naive about life, relationships, love and the trials and tribulations that life brings. Then there are moms, the ones that are still with their significant others and life is seen through rose colored glasses and for some of them they can eventually take of the glasses and their world is good and there’s nothing wrong with that, but then there are single moms… strong, courageous, inspiring, understand that life is tough and and unfare at times but still have an endless capacity for love inspite of it all. They are exotic beauties that deserve respect, and commitment. I too have been hurt quite deeply, from a 15 year relationship. Single moms in general rock! My mom did! And this one that I have fallen for is no exception. So, rejection or no, we can only succed in life if first, we are not affraid to fail! Ask her out soldier! That’s an order! :)

Myself, she never called, I thought my fears were realized, but before fit class the other day I over heard some conversation with her single mom support group friends, generally a group of friendly, high spirited ladies, but that day I got sideways glances and they were all telling her to stay single forever… test number 2, never give up, never surrender. Tell me if I’m wrong, but I believe this is the point where I have to hang it all out there, wear my heart on my sleeve so to speak and somehow prove that I’m not out to hurt her or steal her from her friends. I’m starting by not harrasing her about why she didn’t call, as a matter fact I haven’t mentioned it at all. I’m staying friendly and keeping up the conversation, even though she is in cautious mode. I bought her a “Single Moms rock the play dates” shirt and I know her two daughters are learning to snow board so I’m getting them some day passes to the local hill. I suppose giving them to her on Vallentines day would be over the top? I know she’s been down the Isle twice and is most likely discouraged about future relationships, but walls are ment to be broken. I believe it was mother Teresa that said; “I have found the paradox, that if you love until it hurts, there can be no more hurt, only more love.

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Miami Air Conditioning April 3, 2011 at 7:04 pm

I guess he just need to be honest, when they are having eye contact, he need to take courage and tell her> would you like to go on an date with me?
thats it….

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