20 Tips for Dating After a Breakup          

by Connie Jo Holmes

No matter your age, the idea of dating again is hard. Even if you are somewhat excited about it, it is scary. Before I even get into the list of tips, my advice from personal experience is to take time to get to know yourself again. Especially if you were in a long-term relationship, you have to get to know YOU again and remember what YOU like and what YOU want out of life. When you do this, it is amazing what you will learn about yourself.

My personal experience with this is that both my current husband (the absolute love of my life) and I, ironically, took one year off to figure ourselves out before dating again after a divorce and a rebound relationship. When you take time to “date yourself” you are not only doing yourself the biggest favor possible, but you are doing your future partner the biggest favor possible too. You come into the new relationship confident as hell, knowing that you can stand on your own, and aware of what you stand for and believe in. These are all positive qualities that will take you far in life and provide you with a strong foundation for a new relationship.

You, too, will find love again if you so desire. Please just take the time to identify what love means to you before you start dating again. Let me end this section with this — you must love yourself in order to love another — and it is during your time of self-discovery that you will grow to love yourself.

  1.  Give online dating a try. The beauty with this is that there is a huge pool to select from.  Much larger than your place of employment, the restaurant down the street, or the dog park in your neighborhood.
  2. I have found dating, especially online dating, to be a numbers game. What I mean by this is the more people you talk to and choose to meet the more your odds are of finding a person that is worthy of you and your time. I do not claim to know the percentages, but if you have to date 10 people to find someone who is “just ok,” then maybe you need to date 20 people to find someone who is “ok, he is pretty decent,” to maybe needing to date 50 people to find someone who you want to be exclusive with to see where it can go. Again, I am making up these numbers, but this is what I mean by a numbers game — the more you date the more odds you will have in finding someone worthy of your beautiful self.
  3. Stay anonymous! NEVER let anyone you do not know pick you up at your house or your place of employment.
  4. Stay safe. ALWAYS meet someone for the first time at a public place that you both drive to yourself.
  5. Be smart. ALWAYS tell a trusted family member or friend where you are going, the person’s name and a photo of them if you have it. This is not being paranoid. It is being smart!
  6. Put yourself out there. Whether that is joining an online dating site, telling all your family and friends that you are ready to date again and are open for them to introduce you to people, or whether it is flirting with the single person you run into at Home Depot or a restaurant, do it. With the time you took to get to know yourself again, you should be confident in yourself and know that you are quite a catch yourself.
  7. No pen pals. For me, with online dating, I personally did not want a pen pal. If I was remotely interested in a person, I wanted to immediately meet you in person so I could determine if there was in-person chemistry. I cannot tell you how many people came off my list immediately after I met them in person. For this reason alone is why I give this advice. Why build up excitement and hope only to be highly disappointed after meeting?
  8. Establish early on in the dating what you learned when you were dating yourself. Hopefully that means high standards for how you are treated, honest with what you desire out of a relationship, and no fear to state your needs. A specific example of this is do not fall into the habit of, “I don’t care what we do. You pick.” You do care, or you should care. If you want to go sing karaoke, tell him or her that you want to do this. Do not hold back because it is through dating that you inform the person you like what you are about. Learn early on if it is not going to work out, and by not standing up for what you want, you will never show them.
  9. Start brief. Always have the first date be over coffee or a beer. No meals. A beverage is long enough to get an idea of chemistry and a meal is much too long if you have just met someone you do not connect with at all.  If you like them, there are plenty of meals to be had down the road. Always leave them wanting more!
  10. Give a second chance. If someone was “ok” on the first date, consider giving him or her a second date. Since both people are nervous and have too much going through his or her mind on a first date, with a second date you can concentrate more and decide if it is a go or no-go. This practice hurts nothing and is worth a try.
  11. Always be honest. If you have a second date with someone and decide that you do not want a third, simply tell them that you do not see a match or a connection and sincerely wish them well. You do not need to over explain your reasoning, simply thank them for their time and wish them well.
  12. Be upfront. The same holds true as above but even if you don’t want a first date. If someone approaches you and you simply do not want to pursue him or her for whatever your reasons may be, just tell him or her you appreciate their interest, but you are not interested at this time and wish them well. No apologies necessary.
  13. Do not spend too much time talking about why you are divorced or newly single. If anything, maybe share what you learned from the relationship, the breakup, and the person you are now. THAT is what matters. Telling someone new that your ex cheated on you, emptied the bank account, and has three children with his mistress now does nothing for your first date. All of that can come out in time when you begin to get serious with someone, but the first date is not the time for trash talk. You have your friends and counselor for that!
  14. Take nothing personally. If you like someone and they are not feeling it as much as you are, DO NOT take it personally! I realize this may be hard, but please trust me on this one. You really have no idea where they are in their heads and in their healing process. You may be the best thing since sliced bread, but maybe their last love was a croissant and that is what they know and, therefore, desire right now. Silly analogy, but hopefully you get the point. Do not push a relationship at all.
  15. Leave room for the right one. I dated a couple of people that I thought had great potential and #14 above happened to me. I was bummed at first, and I did take it personally, but what was actually happening was a favor. A favor in that I was not spending my time with the wrong person because that allowed the RIGHT person to come into my life at the RIGHT time. Please believe in this. It is so true!
  16. If you are a woman, do not be afraid to pick up the tab! Although I do believe in manners and respect, I do not believe the man always has to pay for dates. It is no longer 1937 where women do not work or have “lesser” jobs than men. Do not be cheap and do not be greedy. Give of yourself and your money a bit.
  17. Do not play games and ask your friends for the “rules” of how many days should go by before you call or text them. Screw that! If you like someone, tell him or her. If you had a wonderful time on the date, tell them. What does it matter who reached out first? This is another good way to clear out the not so great potential relationships. If you had a great time and texted them that when you got home, and you did not hear back for two days, well you have your answer then, don’t you? Apparently, you had a better time than they did — do not take it personally! — and now you know to keep on looking.
  18. Be warm when you first meet someone. A date is not an interview. A date should not be a vision in your head of walking down the aisle with this person. A date is not sizing them up to see if they would be good in bed. A date is simply a meeting of someone who you want to get to know a little better. If you view it this way you will be much more relaxed, then on subsequent dates you can wonder if they may have serious potential.
  19. Have fun! Look at it as an experience and a moment in time in your life. It is also further self-discovery, which is always a beautiful thing. If they like to hike, but you have never done it before, try it. Even if the dating does not work, maybe you will find a new hobby. Look at it, too, as an opportunity to look forward to something and to get out. Your attitude with dating — and in life! — is everything!
  20. Remember your worth at all times! Being alone yet happy is a million times better than being in a relationship and being miserable. You are worthy. You are enough. Stay committed and focused and the right person will come around when he or she is meant to. All of your life has led you to this moment. ENJOY IT!