I can’t wait to read the comments on this one. Sorry, no advice for you since I’m not even remotely close to being in the same situation but it does scare the crap out of me.

I also worry about my boy meeting my ex’s significant other when that time comes. Ugh, I don’t even want to think about it.

Ugh. This one is a toughie - and one I’m experiencing in reverse since my ex is wanting our son to meet his girlfriend right now. Here’s how I did it:

I had been dating Dan for a couple of months, we had hit it off immediately and knew from the first time we were together (we met online and conversed via email and phone for about a month prior to meeting) that we were a good fit. I brought the topic up with him first and then with my ex. I gave the ex the heads-up on what was going on, and he asked if he could meet Dan before Duncan did, to vet him, I guess. I agreed, they met, and they met again without me involved (I call it their man-date). Once the ex gave Dan the ok, it was up to Dan to decide when he wanted to meet Duncan. It probably took him another month of reflection until he was really ready - not because of any cold feet about our relationship, but because he wanted to be absolutely certain that he was willing to come into Duncan’s life and stay there, he didn’t want to be one of those men just walking through his life, which I appreciated. I think he had to get used to the insta-family aspect of it all too. When they finally did meet, he was “my friend Dan” coming over for dinner. I worked up to it a little so he wasn’t sprung on Duncan, but didn’t make a big deal out of it, and they got along beautifully. Now he’s Daddy #2, so named by Duncan when he was ready to call him that.

You may want to modify this approach a bit because I have a pretty decent working relationship with my ex and I didn’t want it to sour over this issue, but giving everyone involved time to get used to the idea before it happens was key for us. Good luck!

I have been in your shoes and let me tell ya, there is no one size fits all answer to this question (kinda like everything else having to do with parenting). I can however offer my experiences for your reflection. I tried to be cautious, but still ended up making mistakes. Take from it what you will.

I became a single mom just before my son turned seven. He was familiar with a couple of men I had platonic friendships with so when I began dating someone and it lasted about three months, I felt comfortable with the idea of introducing him to my son as a friend. This meant that I had to ask this man not to touch me, kiss me or call me anything that remotely resembled a pet name. He was understanding about it, so we proceeded with the “friend” introduction over dinner at my place. We continued scheduling our dates two times a week when my son was at his dads as to not interrupt my family time with my child. However this proved to be very difficult because the time I was now using for dates used to be the time I spent cleaning, grocery shopping, shaving my legs, reading etc… In order to date this man and keep the rest of my life together, I had two choices; farm my kid out to family or a sitter when he was around or start including my son in our relationship. We tried out both. If I used a sitter on date nights I felt like I was short changing my son out of time with me and if I brought my son on dates I felt like I was short changing the date. You can’t exactly gaze into one anothers eyes, eat a slow romantic dinner and have adult conversation when a seven year old is around. So after several attempts at “kid friendly dates” (going to the swimming pool, PG movies) and feeling uncomfortable with it for various reasons I came up with a solution. I started making late dinners/ watching movies/drinking wine at my place after my son went to bed. But, the late nights caught up to me and I was exhausted within a month. We never did find a balance and the relationship ended after 6 months.

The next relationship I had was with my new hot, next door neighbor…there was lots of sneaking back and forth late at night. I felt like I had found a balance of family time and romance. We included our neighbor friend in more activities than the previous man because he lived close by and he could stop by casually and the fact that my son took to him as a playmate the first time they met. They would run across the street to the park and play and make Lego structures while I cooked or did chores. I met his family, he met mine, he was the perfect man, or so I thought. Great job, great family, chivalrous, smart although he was significantly younger. I hadn’t been this happy in ten years! After almost four months of dating he started distancing himself and he ended it at the six month mark saying he hadn’t been happy with the situation for a while and no hard feelings blah, blah, blah. That was the last time we spoke. He avoided eye contact with me whenever he saw me, didn’t respond to my texts or calls. I couldn’t figure out what went wrong or when. It was very abrupt and confusing. A couple weeks later my son asked me where his buddy was and could he go over and see what he was up to since he saw his car parked outside. I sent a text saying he was on his way over, sorry, he ran out the door before I could stop him… Dude didn’t answer the door. When his lease was up a couple weeks later, he moved… turned out there was another woman…she didn’t last long either. I talked to his best friends girlfriend and she said, “Don’t take it personally, this is what he does. We were surprised you were together for so long. We thought you might be the one.” Umm, a little warning please? Almost four years later my son still asks about him.

I agonized over the feeling of being the worst mother out there EVER and how could I have done this to my child, let his love be given and disregarded… how could I let him become the victim of my love life. I shed many, many tears and there is a place in my heart where I still mourn this.

So after that I vowed I would never, ever introduce him to anyone again until at least after the six month mark. When the “courtship” period was pretty much over and devotion has been explicitly expressed. Also, I decided I would never date a guy who was younger than I or wasn’t ready to have his own children. Needless to say I couldn’t find a guy in his thirties who wasn’t either, already married, or freshly divorced with kid/s of their own… that’s a whole new topic, but dating men who have children already is very, very hard and when you add that to the difficulty of dating a woman who has children …well, I found it ovewhelming. Time and financial commitments and emotional ties Oh my!

There is a happy ending… Two years ago (while I was still man-hating after my last bad experience) I was supposed to meet up with three people I worked with when my son was a toddler. Well, two of them canceled last minute and I ended up on what turned out to be a first date. We had such a great time rekindling our friendship that he drove about two hours every other weekend when my son was at his dad’s for the next six months. Then he started coming every week and that’s when I introduced him to my son as an old friend from when he was a baby. My son loved the fact that this person had “known him” that long and they got along fabulously. After that he decided to move to be closer to me. We had grown up dates when my son was at his dad’s and on the weekends when he was with me we did kid friendly things as well as grocery shopping, washing cars and doing laundry together. Things just started to fall into place naturally. Largely (IMO) due to the facts that he has an amazing family, parents that are still in love and really wants that for himself. We’re getting married in September and my son will be walking me down the aisle.

I wrestle with this topic all the time…but I have soon come to the realization that we are a team - my daughter and I. We are a package deal. You cannot love one over the other - it’s just that simple. It’s up to you when you think it’s time to introduce N-funk to the new dude. If it were me, it would be casual, at your house having dinner - be in your element. Kids, at this age do ’sense’ things, but they are young and flexible - but it’s totally up to you. Good luck.