Dating Again: The Re-Entry Checklist

Dr. Pepper Schwartz
Dr. Pepper Schwartz

I had the pleasure of talking to AARP members about being single and dating after 50 at their annual member event Life@50+ in New Orleans. Here are some of the key points from our discussion:

  • When you want to date again, first consider the non-online possibilities: friends of friends, single events, hobby groups, places of worship, etc.
  • Go to busy places to find a potential mate, such as airports, concerts, political groups, volunteering opportunities. Don't be afraid to chat up people! I figure, go up and talk to someone. If they aren't interested, whatever ... it's their loss.
  • Consider boutique dating sites -- interest-specific sites such as Equestrian Singles, FitSingles, Duet or JDate. JDate is great. You don't even have to be Jewish, you just have to want to date someone who is.
  • Scam alert. It happens rarely, but be aware that some dates are only interested in scamming you. If anyone ever asks you for money, stop and report him or her to the dating website that you are on.
  • Not a connection. If someone tells you they want to be free and don't want to commit, believe them and move one. We are adults; you're not changing them.
  • Pre-date jitters. Make sure you exchange a few emails via the dating site before meeting in person. Don't fall in love before you meet. Take the chance and meet to find out. We come from a time when we think that if we date someone he or she  is just dating us. Don't assume. Ask if you want that.
  • Bad dates. The worst date makes the best story. Have a sense of humor about it. Try not to take dating so personally. It's not going to be perfect all the time. Sometimes it's not about you at all. Move on.
  • New dating rules. There's still a lot of traditional "boy-girl" stuff. Who calls? Who pays? In the United States, sex is expected after a short time of dating, generally four to six dates. Know where you stand and what you want to do. Give people a chance. Initial lack of attraction can be misleading. It might just be that day, that moment.

More tips:

  • Start with a friendship. Don't fall in love too fast.
  • Pace yourself about what you disclose and how quickly you do it. You don't have to tell about your illness, your troubled child. And you should not talk about your ex!
  • Remember to listen. When people are nervous, they talk a lot. Show curiosity, ask questions, smile, be open.
  • Stay yourself. Don't "mirror" and become someone different to try to charm someone.
  • Have a support system. Friends can help give honest feedback. Let someone be your wingman or -woman.
  • Create new fun together. Don't just replicate what you did before you met each other. Try new things!
  • Be cautious with "I love you." Men and women use it differently. It doesn't necessarily mean monogamy or marriage.
  • If it's not right, don't stay. If you've been a pleaser in past relationships, don't do it again. You don't have to settle.
  • Don't let age make you feel that you have to settle. If you go and have fun with someone and it doesn't work out, that's OK.

Highlights of audience Q & A:

Q: I was dumped via text. I find guys want to text and talk sex before getting to know me. What's the deal?

A: You have the wrong guys. Don't wait for guys to look at your profile. Go find the guys you like. Reach out to them and just say, hey, I liked this about you.

Q: I just recently met someone that I view as a friend. I didn't want to hurt his feelings. What do you feel about brutal honesty?

A: Don't trap yourself in relationships you don't want. Be nice but be honest. Say something like "Thank you for the time, I thought this might be something, but for me it isn't. I'd like to be friends if you want to."

Q: How do you do due diligence so you don't get creepers?

A: Get details from their bio and ask more questions. Google them. It's pretty easy to track. Meet for the first time in a lighted place with people around. Take it slow at the start.

Q: I'm dating multiple people on one of the big dating sites. Should I tell them?

A: On a first date, no. But be honest if they ask. It's OK to say, "I'm dating other people, but I'm enjoying getting to know you. I'd like to give it a little time before we decide."

Q: I have a friend with breast cancer and body changes, and she has scars. If you date and start to get intimate, how should she handle that?

A: That's a great test of what love is. If someone really loves you, they want you, not your left breast. You have to be brave. I wouldn't lead with "Hi, I had breast cancer and have scars." That doesn't define you. Let them get to know you first.

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