Difficulty Dating After Divorce

People write in to ASK MIDLIFE BACHELOR with questions.  An index of all Q&As is located on the ASK MIDLIFE BACHELOR INDEX page. Email your question in complete confidence to [email protected].

I have been separated for 2 years now. My husband left me and our small family, a 2 year old then, and a 5 month old baby, for another woman he met at work. We had been together for 10 years, and I followed him overseas because his career took off, and since we had a small family it made sense. I stayed out of work for about 3 years. I spent about one year of my life very sad, and it has been really hard to put it all behind. I have since graduated with a graduate degree and gone back to work while also being a full-time mom. I look after my children closely since I have no family nearby, and I want them to grow up as happy as can be, and not missing a father. The father’s relation-
date escape

ship with that woman failed, after he left from that country he took her with him into his next country and that didn’t work out. Now he is with someone else in another country. In any event, I have started online dating, and I think it is not going too well. I am good looking, smart, educated and friendly, so what goes wrong?

My question is: Is my story so pathetic that I cannot get asked on a second date? Should I just keep it to myself. I feel rejected often, and it is a bit hurtful. I have had 3 dates when the questions start: so why are you separated with such little children? Do you have a nanny? How are you going to be able to date and spend nights away? etc etc. My first date was the one I liked the most, don’t ask me why, I guess I was just attracted to him after emailing back and forth and talking. He seemed educated and charming. SO when he asked me stuff I was honest, I don’t come into these dates flashing my pitiful story, I just answer questions; should I lie?

After he gave me long talks about how I should sue my ex, and make him pay, and how much was he passing me every month, he practically shoved me in a cab and sent me home. I felt so bad so I called him and asked what happened tonight, he responded go to bed you have to go to work tomorrow. And he never called or wrote to even say, sorry blah blah blah.

The second guy we were chatting really nicely, I didn’t get into too many details about my past but did have one too many wines, and we ended up kissing, and he texted me several times, but never again.

The third guy wanted to get into my pants 2 hours after we met. Literally said let’s go into the bathroom and touch. (of course he was out the door and didn’t even get a kiss out of me). The fourth and fifth I haven’t met. At the moment I am writing to two. One is starting with the nanny questions. How frieken annoying. Please advise.


Thanks for writing in – I am sorry to hear you are having a rough time out of the starting gate of midlife dating. Trust me when I say that over time, you will find your equilibrium – and things like what you describe will either no longer happen, or they will no longer bother you.

Here’s my take. You might be sharing a little too much information too quickly with these men when you first meet them. Remember that YOU are in control of what you tell them … so I’d suggest leaving things vague and abstract at least until you get to know them better, and figure out if they are even worth sharing personal information like that with. Another thing to consider is how you actually convey certain messages. For example, instead of saying “My husband left me for another woman” (which makes it sound like something could be wrong with you) … instead say, “My husband had a problem with respect to fidelity” (which sounds like HE was the one with the problem). Both are accurate statements – but the latter won’t make you appear vulnerable.

When someone asks how you are going to date and spend nights away … I would suggest responding with something like, “My children are my first priority – and with respect to everything else, I’ll figure it out when the time comes.” Trust me when I say that any man who either questions or belittles that statement would not be worth spending any additional time or energy with.

My overall advice is that you focus on the “here and now”. Continue to meet people online, and in person – and see if any good chemistry develops. If they annoy you in any way when you first meet them – then believe me, they will annoy you even more later … so just thank them for their time, and say good night. Dating is hit-or-miss … and I suggest not getting offended or depressed if you go through a number of dates without anything good really coming from it. You’ve heard that old expression that states you have to kiss a lot of frogs before you find your prince? That is very true! Each date is a good learning experience, if nothing else.

You might consider reading the section of midlifebachelor.com entitled Midlife Dating Advice. Most of it is written from a man’s perspective, but as a woman you can adapt it, as appropriate. In the Fundamental Truths section, I talk a lot about things like:

Be Happy and Comfortable with Yourself
Don’t Take Things Too Personally
Be Careful Right Out of the Starting Gate

You are in a phase where you are trying to figure out what makes you happy, and you are actually fairly susceptible to a Rebound Relationship right now … which could be a lot of fun in the short-term for you. [See Rebound – Does Fear of Being Single Drive Your Behavior?] Just be careful, and keep your guard up at all times.

You were kind enough to email me a photo, and I will say you are an exceptionally good-looking woman. I am positive that once you find your equilibrium and confidence that you can probably have any man you want. Yes – you are that hot ;o)

Hopefully this was helpful. I encourage you to consider joining our Midlife Forum here on midlifebachelor.com … where we talk about a lot of things, including dating issues. We’d be happy to have you as a member of our community. Here is a link to it:


Take care!!!

Avatar of Greg Smith
About the Author

Midlife Bachelor chronicles lifestyle, dating, and relationship experiences and advice to avoid a midlife crisis. Readers like you are often beyond young adulthood in their 30’s, 40’s, and 50’s that want to understand how dating, sex, relationships, and love fit in with our lifestyles.