Advice on returning to the dating game for the second or third time

When you are in your 20s or 30s, dating is fun and exciting. You have never been married and you are looking for someone to build a family with and begin a life together. However, on the second or third time around, you most likely have been married and may even have a few kids. Dating is very different. You look for different things than you did the first time around. You usually know exactly what you want, and you are not as likely to settle for anything less.

The problem is that this attitude excludes many people and includes very few. You may begin wondering if there is any hope for you at all. The following dos and don’ts will help you get out the door and engage in dating again later in life—whether you are looking for a life partner or a spouse.


Cartoon with check mark

  • have fun
  • keep dates simple
  • put your best foot forward
  • remember that the date is about you

Cartoon with x mark

  • claim or unpack baggage
  • be critical
  • compare dates to your ex
  • have sex until you establish a relationship

[publishpress_authors_data]'s recommendation to ExpertBeacon readers: Do

Do have fun

Remember that the first date is only to see if there will be a second. You are not interviewing for marriage. Have fun and be curious. Dates are lessons in disguise. As a general rule, the person you end up forming a relationship with may not look or be anything like the sort of person you had envisioned. Also keep in mind that a date is NOT a relationship. Don’t scare yourself away from dating because you are not ready for a relationship.

Do keep dates simple

Meeting at a coffee shop is easy and safe. It will give you a clearer picture of who this person is and whether or not you want more.

Do put your best foot forward

Don’t be someone you are not. But do put your best foot forward when meeting the person. A sloppy presentation is never as well received as a put-together one.

Do remember that the date is about you

The date is not about them, it is about you. How do you feel? Is this someone who you believe you would like to know more, or are there red flags flying everywhere?

[publishpress_authors_data]'s professional advice to ExpertBeacon readers: Don't

Do not claim or unpack baggage

People tend come with baggage, which is brought on by years of experience. Don’t claim the baggage of others and don’t try to help them unpack their baggage on a date.

Do not be critical

Always remember that the people who are opinionated or judgmental tend to have less successful relationship opportunities.

Do not compare dates to your ex

There are times when you see things in others that you don’t like. However, assuming a man or woman who does something similar to your ex is exactly like your ex is a big mistake.

Do not have sex until you establish a relationship

No matter what you hear, sex is never a good idea until you have a relationship established. Dating is not a relationship. The best time to have sex is when you are ready to deal with the possible consequences—and that is never on the first date.


It is vital to keep dating solely about the experience, rather than the end goal of finding a partner. If you can do this, you will be more likely end up with both: A great experience and a wonderful partner.

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