I’m fairly certain he wasn’t expecting me to tell him I needed a week’s notice. We’d spent several weeks chatting on the phone and exchanging flirty text messages and going out was the next logical step. He was the first guy I had been receptive to going on a date with following the loss of my spouse over four years ago. Adding to my jitters was the fact that I’d never dated with a child so I was in unfamiliar territory.

The first step in making the date a reality was to decide what to do with my kiddo. I can count on one hand the people I’ve entrusted to babysit her. Plus, 95% of those times have been due to a work-related conflict, attending a funeral or making a trip to the cemetery. I chose to have her, so I make it a priority to not ask family to babysit too often.

I was surprised that my “one week” response didn’t send him running for the hills. It takes a special person to understand all that comes with being an “only parent”.

Kimberly, a member of the Young, Widowed & Dating online support group, finds dating with minor children challenging as well.

“I have no family support,” she explained. “Every time I go on a date, it costs me $10 an hour. Plus in addition to paying a babysitter, I don’t expect the man to pay every time we go out so sometimes I pay. A movie, dinner and sitter can easily add up to $100-$200. I can’t afford to do that.”

Even with support from family, member Giselle is discovering that dating requires lots of pre-planning.

“My son is about to be 10. When I go on dates in the city (New York), I drop him off at his grandmother’s house the day before so I don’t have to rush back,” she said. “The weekends tend to be my only option. On a weeknight, it’s too much back and forth.”

In addition to coordinating a babysitter, many young widows walk a fine line between wanting to find love and companionship again while reassuring their children that their father isn’t being replaced.

Giselle said her son kept begging for a replacement dad not long after she became widowed. As he got older however, he said he didn’t want a new dad and began to fear Giselle would love her potential new partner more. Like many other widows, she now dates secretly.

Another member, Jill, finds her son, who lost his father when he was six years old, has appointed himself the “man of the house”. She said he tends to butt heads with her boyfriend and attributes this to his feeling his role is being challenged or because of jealousy. She works to reassure him that he simply needs to be a kid and that her love for him can never be diminished.

Having lost one parent, children of widows can be fearful that they will lose the surviving parent and at times may become clingy, posing yet another dating challenge.

“My 10 year old feels like he needs to be with me all the time so he knows I’m safe, which makes most everything difficult,” said Sarah.

Quite often, even when things are perfect between a widow and new suitor, there is hesitation to introduce him to her children. Having dealt with the loss of their father, “only parents” worry about causing further trauma should a relationship not work out.

“My kids get very attached once they meet a guy…whether I do or not,” said Kimberly. “If we break up, they assume he has died since they can’t see him.”

Fellow YW&D member Julie understands the heartache that can come with a breakup.

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While a few of these concerns are shared by non-widows, there are certain aspects of dating that are exclusive to the widowed community.

“I imagine dating in your 30’s is complicated for many people,” added Julie. “As a widow with a young child, it’s exhausting and overwhelming.”

Despite the challenges, a man worth inviting into your life will understand the special circumstances that come with being a widow raising young children.

Member Katie has met a wonderful man who knows the unique role he plays in her life as well as the lives of her children.

“My children were both extremely accepting and it really it warms my heart so much to see them all together,” she said. “My boyfriend said early on that he’ll never replace their dad, but he’d step in where my late-husband can’t be. He went with us to the first day of school and we’ve done things together like going to the zoo. Marriage has been discussed and honestly the kids are thrilled. We’re still just taking each day as it comes though.”

Mom to a feisty preschooler, Kerry Phillips became widowed at age 32. She runs an online support group for young widows and widowers venturing back into the world of dating and is a blogger for The Huffington Post.