10 Tips on How to Succeed at Online Dating as a Middle-Aged Man

How to succeed at online dating as a middle-aged man? Basically, the same rules apply to people of all ages. Anyway, there are some tips to be kept in mind.

According to statistics, the divorce rate in the United States is 53%. As a result, the number of single people, especially middle-aged people, is only growing. Middle-aged men find it difficult to start new relationships as some of them are afraid to repeat an unsuccessful marriage. Others have children from their first marriage so they fear that their children will not get along with the new wife. Therefore, the search for women via the Internet can be very arduous and long. We have prepared ten useful tips on how to succeed in online dating and find your love to live happily ever after.

  1. Upload Your Photos

In online dating, you should always use real photos of you, which should also be of good quality.

However, the person in the pictures should still look like you. If he does not, the expectations may not meet reality when the two of you will finally go out on a date in real life.

You should only use a few photos, and they should be cool. If you don't have the right photos yet, you can go to an event where they will be a professional photographer taking pictures of guests. Then you just need to find your photo on the website and download it. Now you have great photos to work with!

  1. Fill out the ‘About Me’ Section Wisely

All women, whether nice American or cute Russian brides pay more attention to the information in the profile while men are primarily interested in photos.

Therefore, it is very important to describe yourself in the best way possible so that a woman would want to get to know you better.

Write about yourself briefly and in an appealing manner. This part of your bio is like a cover, which is the first thing people get to see. An appealing ‘About Me’ section usually contains:

  • a brief description of your interests and hobbies

  • a few words about what your friends think about you

  • a list of things you are hoping to find in a potential partner

  • five things you can't live without

  • last good book you’ve read


Your conversation with women will be based on what you wrote about yourself. Therefore, do not write too much and let the woman ask questions and express her interests.

  1. More Swipes to the Right

Swipe to the right is like establishing eye contact in the bar. Don't be afraid to mark women that you like. The more swipes there are, the more choices you will have.  Do not swipe all women and focus only those you like. Otherwise, the app will recognize you as a bot and block your profile. You have a choice, to whom you can write. You can choose the most interesting women and chat with them. If it is clear that a woman is uninteresting, rude, or just doesn't suit you from the first words spoken, you can always change your choice.

  1. Start a Conversation

If your profile is interesting enough, then it’s easier for you to start a conversation as interesting profiles have a 70% success rate. View the profile of a woman, meet her interests, and ask something about her hobbies or work. For example, a woman writes that she likes to travel. In this case, you can start a conversation like this: ‘Hi! In your profile, I read that you like to travel. What trip was the most unforgettable for you?’ Thus, you will show the woman that you are really interested in her.

Do not be too impudent and don't start a conversation with indecent topics. An example of a bad start to a conversation and how to redo it: ‘Hello. Tell me how to go straight to your heart.’ You should better write, ‘Hi. I know something about you.’ This will show sincere interest in the woman and allow you to then tell her your interesting conclusions you reached by viewing her profile.

Do not be too cute and do not overdo it with compliments at the beginning of the conversation as this will most likely bore the woman than attract her attention.

  1. Individual Approach

When you try online dating, sometimes you can have a number of conversations to keep up with at once. No matter how many women you are chatting with, every single one of them should feel special. They are all different personalities, and you should respect that.

You have to be flexible and creative. Women love attention. So, try to show her how interested you are to know more about her. It's easier to do this on the Internet: you don't get lost and have time to select the most accurate phrases to attract her.

  1. How to Continue? Topics for Communication

When communication is established, choosing a topic for a conversation isn't difficult. Learn about the interests of the woman. Tell her about yourself. Talk about movies, books, travels, pets, weather, favorite places in the city, food and drink preferences. You can share childhood memories or plans for the future.

If a woman is an educated one, you can discuss history, art, or philosophical questions. Of course, it will work only if you have some knowledge of these topics yourself. For example, you can discuss an exhibition that has been opened recently, or talk about an artist or a writer who made an indelible impression on you. The main rule is don't dwell on yourself but be more interested in a woman’s opinion.

  1. Confidence is the Key to Success

What always attracts a woman? Confidence. Do you have it? Start developing this quality right away (there are many courses, books, etc.). Without confidence, it will be very difficult to impress a woman. Women feel men’s confidence on an intuitive level. Male confidence attracts women like a magnet as it is a guarantee of protection, prosperity, and security, which women are looking for in a man. This is especially important for middle-aged women that already have a lot of experience in dealing with different kinds of men.

  1. Think These Points Over in Advance

If you expect to have a long-term relationship, be sure to take everything seriously. Do not avoid talking about creating a family or opportunities to live together in the future. But if you only want to have fun with a woman, don't hide it! This way a woman will not have false hopes and won’t make a tragedy out of your breakup. Neither you nor she needs these problems. So think carefully about what kind of relationship you need.

Another important point is the woman’s family. Decide for yourself whether you are ready to bring her children up or spend weekends with them. If that's a problem for you, explain it to a woman before your relationship becomes more serious.

  1. How to Invite a Woman on a Date

The first thing you should decide on is whether you message a woman or call her. If you have already exchanged phone numbers, it would be better to call her. If you still do not have a woman’s number, you must first get it. For example, as you are ready to go on the first date, you can write: ‘Let's exchange numbers to stay in contact.’ If you are serious about a date, you can also ask some online dating questions before meeting.

A woman should not just be invited on a date but she should be interested. Invite her to go see a movie she has been waiting for, a concert, or a cafe with her favorite cuisine, to the gallery where her favorite artist is having an exhibition. You also can choose one of these options:

  • Choose a quiet cafe where you can have a nice conversation and get to know each other;

  • Walk through a farmer’s market. There you can find tasty meals to go so you can enjoy their company, satisfy your hunger, and do some shopping;

  • Visit a comedy club. It's a perfect place to determine if both of you fit together. If you laugh at the same things, you are a perfect match.


You need to make sure that the woman knows how to get to the place.

It is not necessary to say directly that this is a date, but you can come up with some more veiled reasons and phrases:

  • I know a great place where they serve perfect hot chocolate. Have you tried it? Let's have a sweet tooth day!

  • Next week there will be an exhibition of Rembrandt’s rare works. I remember you saying that you like him. Do you want to keep me company?


If a woman is busy the day you invited her, then suggest another date, but don’t use an abstract ‘someday’ because you may never meet if you don't set a fixed day.

  1. How to Prepare for a Date

Remember that the first impression is very important. Therefore, carefully prepare for the first meeting. Spend some time creating your look. You should be stylish, neat, and smell good. Do not forget about fresh breath as it affects the quality of the conversation.

In addition, think about the topics that you can discuss with a woman in advance. It is better to focus on common and positive topics during the first date. Try not to argue with the woman, especially if you have a hot temper. Do not discuss previous relationships. If a woman decides that you are comparing her with your ex-lover, she will not like it.

  1. Brief Recommendations on How to Behave on a Date

Give all of your attention to the woman. Treat her as if you are already dating. Do not think about the possibility of a second date not to get flustered and not destroy the atmosphere of mutual understanding that has arisen. If a woman has agreed to go on a date, then she’s okay with the thought of dating you. A date will establish how mutually sympathetic you are.

Your main task is to interest a woman so that she will want to continue in a relationship. But remember that it is important to be yourself, enjoy communication, and not be too stressed out.

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