Awesome You Be


David and Merril 

How to Succeed in Dating When You Are Over 40

By Jeffrey Baumgartner

In 2009, my wife of 14 years and I separated and soon after divorced. This meant that for the first time in a long time, I was dating again − as a 47 year old single father with two children. Part of me was excited. Although the divorce was an amicable one, it followed a couple of years of less than marital bliss. Dating other women who might like me was something to look forward to. Also, in the past, I had had a strong professional interest in the Internet and eBusiness, so was keen to experiment with on-line dating, which I had heard a lot about, but had never experienced. Part of me was also apprehensive, of course, it had been a loooooooooooooooong time since I had been on a date; I was out of practice! Since the divorce, I have been on a number of dates, had one relationship of two years that did not quite work, had a couple of very short relationships and have been with mu current sweetheart for the past three years. Along the way, I've learned a lot from experience and by talking with other other middle-aged daters. I am delighted to share today what I've learned with you.

Your Status

Before you start dating on-line, you need to review your current relationship status: are you married, in a committed relationship or single. Only if your answer is 'single' should you be dating again. This seems a very easy review to make, but apparently a number of married people, especially men, are so enthusiastic about the on-line dating scene that they have started dating again without telling their partners. The recent hacking of  Ashley Madison (a hook up site for married people to have affairs) and publication on-line of members' personal information shows how dating while married (or in a committed relationship) can lead to disaster.

However, if you are married, your main concern should not be about getting caught − though there is a good chance you will get caught − your main concern should be that you are being unfair to your spouse, any children you might have and your date (unless she is also having an affair).

Moreover, not only is there a good chance you will be caught by your spouse, there is also a good chance you will damage your reputation in your preferred on-line dating community. Then, when your spouse leaves you and you are ready to start serious dating again, you'll start with a bad reputation.

So, here's my suggestion. If you are married and fancy dating again and, perhaps an affair, do it with your spouse! Ask her (or him) out on a date, treat her like someone hot you've just met and ask for another date afterward. Work towards seducing her. If this doesn't appeal, I suggest seeking couple's therapy sooner rather than later. Therapists specialising in relationships tell me that by the time most couples come to them, it is already too late.

If therapy does not work, separate legally from your partner before you start dating. If nothing else, this demonstrates good behaviour in the event of a non-amicable divorce.

Rebound Relationship

If you are coming out of a long marriage or relationship that failed, it is all too easy to fall for the first respectable person you meet while dating. If you've felt neglected or unloved for some time, being with someone who is interested in you, who is affection to you and who desires you can be irresistible. The thing is, such rebound relationships are a quick cure to heartbreak, but often do not last when you eventually realise that the two of your are incompatible.

Unfortunately, rebound relationships do not feel like rebound relationships until they've failed, at which point it is too late. The best thing to do, if you're coming out of a failed long-term relationship is to take things slowly. Date a few people and take your time before getting into a real relationship again.

On-Line Dating

Cartoon: "I'm sure your incisors looked smaller on TinderOn line dating is pretty much the standard for meeting potential dates these days, especially if you do not have a  social circle full of single people. Moreover, it is a very acceptable way to meet people; a vast proportion of new marriages and great relationships (as well as some dismal ones, of course) started via on-line dating.

If on-line dating interests you, start by taking a look at the various sites − there are a lot out there. Some are general dating sites, some focus on a niche, like vegetarian dating or single parent dating. Most will let you do some browsing free, but will require payment if you actually want to contact someone, see more pictures or get more information. Others are always free. The advantage to the paid sites is that you know the people you meet there are serious enough about dating to pay to use the site. So, there is likely to be less riff-raff and fewer time wasters.

When you are ready to start your search, you'll need to create a profile. Find a nice photo or get one taken. Avoid using an arms-length selfie; the wide angle lens setting at close range will distort your features. Ask a friend to take some pictures or visit a professional photographer to get pictures taken. You'll pretty much need an image in order to be taken seriously by potential dates. You will also need to complete a profile. Okcupid, a mostly free dating web site, also publishes a lot of research into dating. Take a look at their Oktrends for insights into preparing your profile.

I won't give you a lot of advice about using dating sites − there is plenty of information out there already. Just three tips. Firstly, be honest in your profile. If you use a picture that is 10 years old, you might get more initial queries, but dates will be disappointed when they meet you in person, not because of your age but because of the obvious deception.

Secondly, be realistic in your expectations. If you are 50, don't aim for dating sexy 25 year olds. For the most part, they are looking to date other sexy 20-30 year olds. Those keen to date older people (especially men) are often involved in scams, which I'll explain in a moment. Thirdly, if you meet someone interesting on-line, have a real life meeting soon. This is not to say relationships with an age difference do not work; only that you probably will not find such a relationship on-line unless you are famous, rich or both.

Thirdly, if you find someone interesting, arrange a face to face meeting soon. If you spend too long in a chat-based relationship before meeting, you are both likely to form expectations about the other that will be disappointed when you finally meet up. Better to find out early if you are compatible.

On-Line Dating Scams

Watch out for scams, especially on the free sites. Typically, if you are a heterosexual man, a scam involves a very attractive younger woman showing interest in you very quickly − probably unreasonably quickly. For women, it is usually a senior and very handsome person in the military. The aim of the scam is to build a relationship with you on-line. Eventually, that person will need some money. Maybe her mother is very sick. Maybe he is stuck in Iraq and has had his passport stolen. Probably, she is in another country and will ask you to send her money to buy her a ticket so she can fly to you. After you do that, there will be some visa problems that need money. And something else and something else until you realise that she is never going to visit in spite of all the money you've sent her. At this point, she disappears.

One of the telltale signs  of a scammer is that she will want to move the conversation to email immediately, that's because she knows that she's likely to get caught if she uses the dating site's messaging service. So, be doubtful of a very interested prospect who seems too good to be true, refuse to take the conversation off the dating site until you've met in person (this also ensures she does not get your email and share it with other scammers) and do not send money to anyone.

I've never been a victim of such a scam, but I've heard of cases where na├»ve people have sent thousands of dollars to fraudsters. 

Tinder, Grindr and Similar

A few years ago, Grindr was launched for gay men. It was so successful that a similar app, Tinder, was launched for the heterosexual community. They are mobile apps. You sign up, often through Facebook, make a profile and add some images. Then, you flick through pictures of potential dates. If you are not interested, you go to the next picture. If you are interested, you swipe to indicate you fancy the person's picture. If that person also fancies you, you are notified and connected so that you can follow it up. If she does not swipe, she will never know that you expressed interest.

Tinder seems to have a reputation as a tool for easy hook-ups and casual sex rather than serious dating, so bear that in mind if you experiment with it. Tinder came out after I got involved in my current relationship, so I have never used it.

Off-Line & Semi-Off-Line Dating

With all of the on-line dating options, it's easy to forget that you can meet people off-line and semi-off-line. By semi-off-line, I mean a relationship that was somehow initiated off-line, but was enabled thanks to Facebook or another social networking site.

For example, if you are newly single, check out your Facebook friends from school and university. If someone whom you had a crush on years ago is also single, suggest a friendly meeting. You may well find that she once had a crush on you too and would love to get to know you better. I've seen two such relationships occur between people who went to the same international school I went to in the late 70s.

If you are newly single, think about joining clubs and groups that interest you, both to occupy the extra time you have as a singleton and as an opportunity to meet people. One of the problems with on-line dating is that it is based on compatibility, so you are likely to meet people with similar interests to yours, but you are less likely to meet someone whose interests and background are so different to yours that you'd never be connected. At the Brussels Imagination Club, a group I co-manage with a friend, we've seen a few relationships spark and grow. My ex-wife met her current partner at a badminton club they both belonged to.

I believe another problem is lack of smell on-line. Smell is apparently a very powerful element of attraction. Yet it is one that cannot be replicated on-line or in an app − at least not at present.

I first met Inge, my current partner, a dozen years ago when she was the remarkably attractive second year teacher of my eldest son. She was also a great teacher. But she was my son's teacher and I was still married then, so I kept my thoughts to myself and interacted with her as the competent teacher that she was. A little over three years ago, we met up again and I learned that she had also found me attractive all those years ago and likewise kept her feelings to herself. As we were both single, a lovely relationship soon developed.

So, it is perfectly possible to meet dates without the Internet, although Facebook, email and Skype help those relationships develop.

First Date

Unless you already know your date well − for example: she's a part of your social circle − have your first date in a public place such as a coffee shop, pub or cafe. That way, if your date turns out to be a lunatic, you will be relatively safe. I suggest that you agree to meet for a drink in the early evening. If it goes well, suggest going out to dinner. If you are not impressed, keep it to the drink and claim you have another appointment if your date wants to go out for dinner.

In traditional dating, the man was expected to pay for the drink and dinner. But, when I was dating, I found that most women preferred to split the bill. I believe this is in part to demonstrate independence and to ensure there is no sense of obligation towards the man. I also understand the matter of who pays varies depending on where you are dating. My suggestion to men is to offer to pay (not doing so may be perceived as being cheap), but graciously accept if the woman wants to split the bill. If she should insist on paying for the entire evening, accept under the condition that she lets you pay next time. If you are a woman, I would suggest splitting the bill.

Sex on the First Date

As a rule of thumb, if you have sex together on the first date, there will be no second date. I am not sure why this is the case, but it is my own experience and the experience of others. So, if you are really attracted to your date, but do not necessarily want to explore a relationship with him, feel free to have sex on the first date, provided that is what you both want. To this end, avoid drinking too much alcohol on your first or early dates − when you are drunk, you may agree to do things you do not really want to do.

If you like date a lot and want to get to know him better, curb any immediate desires and tell him you'd like to see him again.  In any event, if there is even the slightest possibility of sex, bring condoms, even if you are sterile. You don't know who else your partner may have had sex with and you do not want a sexual transmitted disease a souvenir of your one and only date!

Second and Subsequent Dates

As you get to know your date better, you can be more relaxed about where you go out. But, if you have any question about the safety of your date, keep dates in public places.

By about the third date, I recommend a daytime activity date such as a hike, a bicycle ride or a visit to a nearby attraction. It will be different, fun and you spend time with your date in a completely different atmosphere than night time dates. It also ensures your date is not a vampire!


A lot of people worry about when is the right time to have sex with a new partner and the answer is, whenever is right for both of you. That might come after three dates or it might come after months. If you are religious, you might even feel a need to wait until you marry, though I think that's dangerous. It's better to find out if you are compatible in bed before making the commitment of marriage.

Kids and Dating

If you are in your 40s or 50s and dating following a failed marriage, one or both of you is likely to have children and this can complicate things. You may find yourself in the position of sneaking kisses on the sofa when your kids are out of the room and recall that you used to do the same thing when your parents were out of the room.

If you have kids, I suggest introducing them to your partner relatively early in your new relationship, but introduce her as a friend. Likewise, meet her kids early on or organise an activity in which both families do something together. Because, let's face it, if your new partner and your kids do not get on, your relationship will not work either. The good news is, however, that your kids want you to be happy, so they will be easier to win over than you may fear. Provided your date is a nice person − and she surely is − and she is respectful to your kids, it will be okay.

However, over the longer term, there may be some challenges. As a parent, your first priority and first love will always go to your kids (or, so I would hope). This can be difficult for a childless partner to fully understand and he may feel neglected, especially when you have to cancel a date because of a child related issue. This is also something to bear in mind if you have not got children but are dating someone who has got children. Unless those children are grown up, they will always come first.

If you both have children, that will be less of an issue. However, as your relationship develops, you may run into conflicting rule sets. If your children normally stay up late on weekends, but hers go to bed at eight o'clock, that may prove difficult when you are all together. Generally, the kids will want to follow the partner with the more relaxed rules in any given situation!

Fortunately, in my case, my sons are respectively 11 and seven years older than Inge's son. So, there is less comparison of privileges and rules than there would be if they were all of a similar age.

It's Not Changed that Much

All in all, dating rituals have not changed a lot over the years. What has changed is how you meet people. And that can be a problem. On-line dating and dating apps present a seemingly unlimited choice of potential dates who could become life-partners. As a result, it is easy to keep dating hoping to find the perfect partner. But the truth is, the perfect partner only appears when the two of you undertake the commitment and effort to make your relationship work.

Good luck and share your dating stories with me!




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