Category Archives: dating advice

Jackie, I’m recently single and I’ve been in a relationship for so long that I forgot how to talk to women. Also, will I have patience for the games?   Recently single is a tough place to be. It’s scary, your self-esteem probably isn’t...

Jackie, I need some dating advice. Say you go out on two first dates on two consecutive nights and they’re both awesome. How do I not F* this up?   Do you realize how many men and women would KILL to be in your shoes? Over and over aga...

Jackie, I need some dating advice. I’ve been on a handful of dates with a woman, who my gut says is a truly sweet, genuine woman. We’ve had great dates, talking, laughing etc. for hours on end.  I’ve expressed to her that I want to see her...

Ever been on Cyber Dust? Try it out! I have had a lot of fun on the relatively new social media outlet, which is partially owned by Mark Cuban. I have made lots of great connections with business owners offering advice. In my opinion, Cyber Dust is s...

A single dad dating asked me this question:   Is it wrong to not want to go out on dates unless you feel there is potential for a long term relationship? As a divorced dad who has full custody of my 13 year-old daughter, I don’t have time to...

I received this email from a divorced man who is about to start dating after divorce. How do women feel when they hear that a man is divorced? I feel that when I start to date, they’ll turn away, thinking that there is something wrong with me si...

What dating advice would you give a recovering womanizer who ruined a 23 year marriage? Developing a relationship has turned out to be much harder than having affairs with single and married women. Not proud because I hurt a lot of people in the proc...

If you’re a young, single guy in your twenties, who better to get dating advice from than a middle aged divorced woman? (me.) Think about why it makes sense. I can talk about the mistakes I made, I can tell you what I liked and didn’t like, both ...

What do you think? Should this divorced dad go on dating websites?   Hi Jackie, You have had some good advice in the past and now I am at another point looking for some help.  About a month ago I broke off my relationship with my girlfr...

When it comes to dating after divorce, everyone has his or her own timetable. There are so many reasons that can cause apprehension: the lingering hurt from the divorce, kids, bitterness, fear of feeling awkward, shyness, insecurity, or the worst one...