Posts Tagged ‘dating a single mom’


Last night, after work, a group of friends went for appetizers and drinks at our favorite watering hole, Flanagans. After the 3rd round had passed our lips, and the world was good, and every girl looked gorgeous, our server (whom we all have known for a while) sat down and posed the following question to us. It was, would any of us ever date a woman with children. Sounded simple enough, but posed more questions than answers. Enough that half of the bar crowd joined in on the now debate. It became a round robin discussion, with everyone putting their two cents in on it.

First off, let me state that our waitress is a single mother, aged 30something, with 3 young children while at my table, we ranged from the mid 40’s to the mid 50’s, and were all single males, me being the oldest. After the initial MILF jokes, we actually, seriously, started an intelligent debate on the subject at hand.

What we first said was unequivocally NO F#@king WAY! OK, that was the alcohol causing snap judgments. Upon further discussion, we all had a similar take on the question. While we really felt that it didn’t matter to us if the girl had children, we first wanted to know if she had any contact or attachment to the children’s father. This was to see the degree of baggage that could possibly follow if dating her. The second point that came out was a consideration as to the age of the children in question.

When you are in your 40’s-50’s, there is a very good chance that her kids might be in the 20’s, and that is not a kid, that is an adult! And furthermore, chances are that an adult kid might not like the idea of mom seeing someone who is not their father! Valid point, huh! So we first are seeing the possibility of baggage, followed up by drama. Alcohol or not, we all agreed that our answer would be NO to dating older women with older kids. Baggage and drama were too much to deal with. Then some younger people joined in to the discussion. They ranged from 21-maybe 30. They had a different perspective on the issue. For them, being younger meant that the children would probably be a lot younger, and a lot easier to win over if they dated mom. Good point!

So, when our waitress came back to our table to have our answer, we retorted with, We would like another round, please and wish to remain single!


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