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Three strikes but not out

Updated: September 5, 2013 4:33PM

Greg is the 43-year-old divorced man with custody of his kids. He’s the teacher with the 9-year-old minivan with suspicious stains on the carpet. He’s the one who can’t get a date once women find out The Big Three: kids, teacher, minivan.

It’s not just that he has kids, it’s that he’ll only date every other weekend when they’re with his ex-wife, and he won’t introduce a woman to them unless there’s a good chance for a long-term relationship. If women aren’t turned off by that, then the teacher salary usually does it. The minivan is the coup de grace.

They never stick around long enough to find out that Greg has a large inheritance that makes his life very comfortable and allows him to live in an upscale neighborhood.

Things weren’t looking up for Greg, romance-wise, until he became reacquainted with Joy at a friend’s barbeque.

“She’s very successful and well-educated. She never told me of her Ivy League education until I asked, and she could care less that I went to a junior college and then transferred to a state school. “She isn’t at all pretentious, and if you saw her walking down the street, you wouldn’t know that she’s very successful and wealthy.”

As far as The Big Three go, Greg’s kids were at the barbeque, and so was his minivan, and Joy knew he was a teacher because they’d met 10 years earlier when her now college-age son was in his class. And she was still interested in him.

He was very open about having custody of his kids and having strict rules about dating. She was still interested in him.

“She respected all my boundaries regarding my kids, and that was really important to me.”

Greg says, “I’m nuts about her, and I knew that I was head over heels three months into the relationship. I think it took her a bit longer, but she’d been really hurt in the past and was guarding her heart. She says that so many men she’d dated were either scared off by her success or were trying to freeload off of her.

“She didn’t meet my kids again until 10 months after we started dating. The best part about waiting was that we were easy with each other and my kids could sense it. That made it easy for them.”

They’ve been dating for a year now and they still see each other mostly when the kids are with their mom, but occasionally they all do things together.

“My kids really like her and know that she’s my girlfriend. We’re taking things slowly, and I swear this is the healthiest, most fulfilling relationship I’ve ever had. While I’m in no hurry, I do think I want to marry her someday. This is a change for me, because after my divorce, I didn’t think I’d ever want to marry again.”

Greg says he thinks he knows the secret to what makes their relationship work despite the fact that Joy is wealthier and better educated.

“We’re both confident and secure about where we are in life. She didn’t feel the need to mask any insecurities by flaunting her prestigious education and stock portfolio, and I felt no need to try and be anything other than who I am.”

How do you handle having kids and dating? Send your tale, along with your questions, problems and rants to And check out my new website:

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