Midlife Dating: The Good, the Bad and the Ugly

One thing that I never set out to become is an expert dater.  In my youth I was always in long-term serious relationships, but at midlife, I found myself divorced, out in the dating world again, and can safely say I have become somewhat of a reluctant expert.  There’s no point in developing any expertise, if you don’t share it, so that is what I am setting out to do here.

One thing that I never set out to become is an expert dater.  In my youth I was always in long-term serious relationships, but at midlife, I found myself divorced, out in the dating world again, and can safely say I have become somewhat of a reluctant expert.  There’s no point in developing any expertise, if you don’t share it, so that is what I am setting out to do here.  What follows is a summary of the various ways I have put myself out there to meet prospective dates and my own analysis of the pros and cons of each approach.  I am hoping that someone can benefit from my years of trial and error.  I should add that this summary is based purely on my own experience and someone else may have a very different experience.

Online Dating:

Pros:

 

It is cheap, easily accessible and almost everyone is doing it.  There are many free sites so the only cost is your time.  You can do it from the comfort of your own home, chat with people at your own comfort level and you have complete control over the process.  You don’t have to respond to messages if you don’t want to and it is easy to block someone if they are bothering you.  I have met many nice people from all walks of life, education levels and various incomes.  Most of the people on the paid sites are also on the free sites so there is really not a lot of reason to join the paid sites, and I personally have not found them to be any better.  It is an easy way to meet people that you otherwise would not have the opportunity to meet.

 

Cons:

 

It is cheap, easily accessible and almost everyone is doing it.  This means that in addition to the nice, normal people, there are many weirdos as well.  The only cost is your time, but this can be a big cost because it can become very time consuming reading through endless messages from people you have no interest in, or sending endless messages to people who never respond back and you have no clue why.  Unfortunately, there are a small number of people who lie on their profile about their age, size or marital status so you don’t always know if you take the time to meet someone if the person you were expecting will be the one who turns up.  There is also still a bit of a stigma about online dating and some people are embarrassed to admit that this is how they met.

Overall Recommendation:

If you keep your expectations manageable and don’t take it too seriously, it can be an easy way to meet someone nice who turns out to be just what you are looking for.  In this day and age, it is definitely an effective avenue to meet people.

Matchmakers:

Pros:

 

Candidates are screened to some degree so you can be more confident of meeting the person that was described to you.  The fact that there is a fee involved eliminates some of the riffraff that you have to sort through with online dating.  It doesn’t require a lot of time as the matchmaker matches you with people who then contact you to set up a date.  Ideally you specify exactly what you are looking for and are matched with others who meet your criteria.

 

Cons:

 

It can be very expensive.  Matchmakers I have used ranged from $1000 to $5000.  Many of the people that I was matched with, I have later come across on online dating websites so I could have possibly met them for free.  In my own experience some of the matches were very good and some were terrible.  One company I used seemed to have no rhyme or reason to the matches they sent me. The companies that I used described the matches to me over the phone, I was never given any photos, and I could say yes or no to receiving a call from the prospective match.  If you turn too many people down the company will be upset with you, so you are encouraged to be open to whoever they recommend.  Although candidates are supposed to be screened, one match who I was sent that I spoke to on the phone described to me how he had outstanding charges for domestic violence and what a joke it was.  I couldn’t understand how someone in this situation had made it through any screening process especially given that my job at the time was the lead prosecutor for domestic violence offences in my office.

Overall Recommendation:

Save your money.  You are just as likely, if not more likely, to find what you are looking for through one of the other approaches.

Speed-dating:

Pros:

 

If you go with a friend or group of friends, it can actually be a fun night out.  You don’t get stuck with someone you don’t enjoy talking to since each mini date only lasts for a few minutes.  You spend enough time with each prospect to assess whether you feel any chemistry and whether you would like to get to know them further.  You will only be contacted by those who expressed a mutual interest so you don’t have to worry about being bothered by those you have no interest in.

 

Cons:

 

Speed-dating events tend to be held more for younger age groups.  It is very difficult to find an event that is open to women who are 50 and older.  It is easier for men.  The event is only as good as the quality of the attendees.  I did one speed-dating event that was great and another one that was terrible.  If there are too many people, it can become a bit of a blur trying to figure out who you liked the most.  Also, you are sitting down when you chat with everyone so if height is important to you, it can be difficult to notice the other person’s height.

Overall Recommendation:

Go with a friend or two and make it a fun evening out.  You may just find what you are looking for.

Singles Events:

Pros:

 

If you go with a friend it can be a fun way to spend time.  There are singles parties, wine tasting, cooking, hiking and a wide range of events that can be attended through Meet-up or Match.com.  If you pick an event that is of interest to you, chances are you will have fun even if you don’t meet Prince or Princess Charming.  It is a way to find a partner with similar interests.

 

Cons:

 

Often these events have a younger crowd and if you are over 45 there may not be many people in your age bracket.  Check to see if there are events with a suitable age requirement.  Early on at an event you can get cornered by someone who stakes you out as theirs and it can be difficult to extricate yourself from this and meet other people.  I attended a dance with a girlfriend and we both got “claimed” early in the evening and few other men would approach us as it seemed like we were with the guys that wouldn’t leave our sides.  If you attend many of these events, you can become too much of a regular and there is less interest in you.  “Fresh meat” is always the most desirable.

 

Overall Recommendation:

Pick an activity or event that you enjoy and go with a friend.  You can always leave early if you aren’t enjoying it and at the very least, you know your will enjoy time with your friend.

 

Whichever approach you decide to use, the most important thing to remember is to just have fun.  If you can use some coaching on returning to dating after being newly single and over 40, let’s chat.

Leanne Townsend Lawyer and Divorce Coach
Leanne Townsend is a multifaceted entrepreneur and attorney experienced in the areas of family law and domestic violence. She provides a full range of family law legal services in addition to running workshops and other programs to support people as they go through divorce.

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