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Dating A Single Dad?


Are you really what he’s looking for? Listen in as 5 men reveal what women must know before they go out with a guy who has kids.

By Lambeth Hochwald

For single dads, life isn’t exactly like Sleepless in Seattle, in which Tom Hanks has a son who is so determined to set him up that Dad ends up on a first date atop the Empire State Building with Meg Ryan. Fabulous in fiction but not exactly realistic. Instead, single dads say they spend far more time explaining their custody agreements and kids’ soccer schedules to the women they see. To help you navigate the idiosyncrasies of dating a single dad, we put together a panel of five fathers and asked them to be 100 percent honest about what they’re looking for in a woman.

The Dads:
Robert Grand, 39, special-education teacher; Phelan, California
Divorced for three and a half years; has a daughter, age 10; now engaged to a single mom
Dan Grogan, 42, engineer; Albany, New York
Divorced for less than a year; has a 12-year-old daughter and a 10-year-old son
Mark Kasserman, 47, video producer; San Rafael, California
Divorced for 11 years; has two sons, ages 11 and 13
Patrick Morris, 43, public relations director; Saratoga, New York
Separated for two years; has a son, age 6
Darryl Wooten, 50, actor; Boston, Massachusetts
Divorced three years ago; has four children, ages 16, 14, 12 and 9


What’s the most important thing for a woman to know when dating a single dad?

Darryl Wooten: Any woman who dates me must know that my kids are everything to me, so if a woman isn’t into my children, it’s never going
I’m going to talk about my kids on a first date.
to work out. But she also has to be genuine about them—I don’t want her pretending that she likes them only to get me to go on another date. Believe me, I can tell if she’s sincere.

Patrick Morris: I want a woman to know that I’m going to talk about my kids on a first date. I once went out for a date with a woman who didn’t want to know a thing about my son. Every time I brought him up, she changed the subject. I’d never go out with her again. When you’re a parent, your life revolves around your child.

Robert Grand: Any woman who dates a single dad needs to scale down her expectations and not expect to meet a single dad’s kids right away. Also, a lot of people, including single dads, have crazy exes. I personally have broken away from my old life with my ex-wife, but there is a lot of stress when it comes to dealing with an ex, and any woman dating a single dad needs to know that.

Do you prefer to date another single parent and why?

Mark Kasserman: I’d go out with both but there are pros and cons for each scenario. If a woman has kids, she knows that you can’t just bail and go out for sushi whenever you want—a single woman without kids might not understand that. On the other hand, it’s harder to get together with a single mom because you both have households to run, and it’s often hard to find time in your schedules that works for both of you.

Robert: Let’s not forget about the fact that when you’re dating a single mom, she understands what the dynamic is about. For example, she may be dealing with the same issues as you are — like custody or trying to organize schedules — and she’s likely to be more empathetic.

Dan Grogan: I think what might be a sticking point with a single woman without kids is the fact that I don’t know if I want to have more kids. So, if she wants kids, that’s going to be an automatic conflict. On the flip side, most single moms are done having children, so that makes dating them a lot easier for a guy like me.

Patrick: If I’m looking for a long-term relationship, I would prefer another single parent because she has a better understanding of what your own life is like. She gets the fact that sometimes you really do need to cancel something at the last minute because something really did come up with your child—and you understand that the same thing can and does happen on her end. She also understands that sometimes you’ve been running with your child all day and you really want to see her, but you’re hoping it would be OK for the two of you to just order a pizza and curl up on the couch with a movie.

At what point do you introduce a woman you’re dating to your children?

Robert: I think it’s important for women to know that we as single dads want women to let us figure out when the timing is right to introduce them. It’s not that we’re keeping you a secret from our kids but we want to be sure we’re going to be serious. I usually introduce a woman when I think things are going to work out long-term.

Mark: I used to introduce my kids to my dates but now I wait a little longer because my kids are at an age where they bond really quickly to people. I also think it’s not a good thing to keep bringing people in and out of their lives.

Dan: Right; I wouldn’t just bring a date over to say hello. I’d have to be going out with her for at least six months before I’d invite her to meet my kids—I just think it’s best that way.

Should your date take on any kind of parent/mothering role?

Robert: I think it’s important for a woman to start slow when it comes to mothering a single dad’s kids. It’s
If you see that a kid isn’t warming up, be yourself.
good to show that you’re interested and that you’d be a good mom but you don’t want to take on too much too fast.

Dan: And another thing—I think any woman who dates a single dad needs to keep in mind that there’s also a real mom in the picture and if you take on the mothering role too much, that’s not going to play well with the kids. You absolutely have to ease into that role.

Let’s talk about public displays of affection. What, if any, is appropriate and when?

Mark: I think showing your affection is the best thing you can do in front of kids, but my situation is different because their mother isn’t involved in their lives at all. Sons tend to be very possessive about their moms and, obviously, I don’t have that dynamic. I really believe most kids want their parents to be with someone.

Robert: I don’t have a problem with PDA as long as it’s not inappropriate. I kiss my fiancé all the time in front of the kids but that only started once I knew we were going to be getting married. In fact, before I proposed, we always slept in separate bedrooms—I thought that was the right message to send to my daughter and my fiancée’s son.

What should women know about sleeping over? What works and what doesn’t when it comes to the kids?

Mark: I think you incorporate that into your relationship. I’m very much into the fact that this is normal and healthy. It’s only bad if you traipse seven women into your house over a two-week period. That’s not healthy.

Robert: Honestly, I didn’t ever have a sleepover in the beginning of my relationship with my now-fiancée, Lisa. We slept in separate rooms until we got engaged. Once we got engaged, we explained to the kids that sleeping in the same bed was OK. It also helped break in her son and my daughter in stages. You don’t want to shock them.

Should a woman you’re dating ever approach your child on her own and make plans?

Dan: I think it would be OK for a woman I was dating to invite one of my kids to do something together. I’d have to trust her and, fortunately, my kids are old enough to decide for themselves if it’s something they feel comfortable doing.

Robert: Yes, but I don’t think a woman should make plans directly with the kids. When this woman I once dated started approaching my daughter to make plans, I had to talk to her and remind her that we’re casually dating and that we have to see where the relationship is going. She was way too overzealous for my taste.

Mark: One last thing: It’s also crucial for a woman to watch out for potentially hot-button topics. For example, I was getting to know this woman and had brought my kids along with us for dinner. Right in the middle of dinner, she started talking about her younger partying days and how she used to smoke pot. I’m as open-minded as they come, but no one should ever talk about anything that’s politically questionable in front of my kids. She was off the list right away. It bothered me because you first need to know the parent’s take on a subject before you bring it up. For example, a parent might not think that watching a movie that has two people kissing in it is appropriate, but the person you’re out with might not think of anything of it. You should know what your date’s feelings are on these subjects and you shouldn’t try to buddy up to the kids.

How do you handle a situation when your kids just don’t warm up to your girlfriend? What can the woman do to ease into a relationship with them?

Mark: If my kids don’t warm up to a girl I’m seeing, then she’s out. I’d certainly ask my kids why they don’t like her, but if they don’t like her, there’s something wrong that I don’t see.

Robert: But a lot of times kids are trying to manipulate you or test you. So my biggest advice to women is that if you see that a kid isn’t warming up, be yourself. I think that if you almost ignore it, eventually the kids come around. Also, I think it’s important to note that you shouldn’t take it personally. Kids are coming in with their own baggage and they may be afraid of being hurt or getting close.

Patrick: What I would do right away is sit down with my son and find out specifically what his issues were and if they were real issues or was he just feeling insecure. If it was insecurity, I would do whatever I could to reassure him that I love him more than anyone in the world and that I want him to get to know my girlfriend before he decides that he really doesn’t like her. At that point, we’d have to play it by ear. You need to listen to your heart but you need to listen to your kids, too.


Lambeth Hochwald is a writer based in New York City. Her work appears regularly in Marie Claire, Redbook and Real Simple, among other publications.
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