Second chances are tough to figure out. In some cases, a second chance is exactly what you need while in others, it’s a total disaster. Here are answers to some of the most common queries about second chances in the dating world:


Q: If you were me, would you have gone out with some of the guys who I decided not to contact?

—Danielle, 35, Washington, DC

A:  It really depends on the reason you didn’t want to contact them. No attraction whatsoever? No need to email them (or email back). One thing in the profile that potentially seemed iffy? Go for it since there’s nothing to lose. My philosophy is to open all the doors at the outset. You can always close them later if you want to (after a few emails or a date), but you might as well give yourself the chance.


Q: Is it worth it to go out with someone you’re just ‘meh’ about from the profile? Is it encouraging or discouraging?

—Randi, 52, New York, NY

It’s both. Sometimes you walk into the bar/coffee shop/restaurant, and you know immediately that there’s just no way this is going to work. That’s discouraging, of course. But even the bad dates make for great stories sometimes. Remember that you never know if you’ll have chemistry with someone until you meet in person.


Q: I just want to make sure there’s some potential there before we jump into a date. I don’t think she is my type. You probably hear this a lot. Maybe you will be able to teach me to expand my perspectives and I can go with the flow a little more.

—Larry, 46, Charlotte, NC

A: My philosophy is to open many possible doors (go on many dates) before you decide whether or not to close them rather than closing doors before giving people a chance and getting to know them. You just never know the “type” until you meet in person, and in my opinion, more dates are better than fewer. I actually liken it to clothes shopping for myself. I’m only 5’1”, so it’s hard for me to find pants that are the correct length. Rather than finding a pair I like and then being disappointed if it’s not in my size (only emailing women you like and then being disappointed if they don’t respond), I search all of the clothes just to find my size and then decide if I like the pants (email and go out with more women and then decide if she’s for you). It makes the pool larger, and it’s all a numbers game.


Q: I did not at all like the sound of him from his profile. For one main reason, he admits he’s had two significant relationships, yet he can offer no lessons learned. Nor can he delineate what he’s looking for in a partner. To me, those show a lack of introspection. Either he’s unreflective (which is definitely a non-negotiable for me), or he’s emotionally closed off. I think my assumptions in this case are reasonable. But if something seems glaringly unfair, I welcome your feedback. Thank you!

—Larissa, 39, Washington, DC

A: I think some of your assessments are fair, yet I also think you’re reading into things too much. You can really only make these assessments after meeting someone. For example, while I personally may write in a very jovial way, that doesn’t mean I don’t have an introspective side. It simply means my profile didn’t show that side. I’m not saying you have to like this guy, but I wouldn’t put too much thought into analyzing every word of the profile. Just because he didn’t write it doesn’t mean it’s not present.


Use the tips described here to help you figure out whether it’s the right time for a second chance or it’s time to let go after the first try.


  1. Sometimes it takes an expert to steer us in the right direction. Thanks for the advice Erika, I know I’ll rethink some of my dating decisions.

  2. Hi Erika – I’m an older woman (70) with the brain and looks of a 50 (well maybe the brain is even more ridiculously childish) … anyway, it’s hard to find matches in my age appropriate group who are also interestd in me. I made a 50-100 mile geographic limitation and, realistically, think that’s the best way (otherwise how can one readily get together for a date) but find that within the few I might like to meet, some live in other states. Normally long distance relationships are a total deal breaker for me but in this case, with age availability so restricted, what should I do? Contact or not?

  3. I am 66 and feel the same way – however I would not uproot myself for someone living far away. I have my family and friends and a job and a network right where I live – unfortunately no decent man but I would still hold out for someone close by. And I certainly am not interested in someone moving to where I live from another state or country to be just with me. Too much pressure – I think it is important that two people have their own lives which includes friends and family and activities that the two of you don’t necessarily will do together. Now if you don’t mind travelling or having them come to you then go for it.

  4. To the ladies who refuse to relocate or to have someone move to them, you aren’t seriously looking for a relationship. Open your horizons. If your comfort zone is your top priority don’t complain about there being no guys just knocking on your door. I live in the Atlanta area but realized if I don’t want to settle I need to open my geographic boundary to find the right woman. Neither of you are willing to compromise, so you aren’t really interested in a relationship, you are looking for a convenience.

    1. Brian,

      It sounds like you’ve had some bad experiences, and for that, I’m sorry. But, saying that women who won’t relocate are not looking for a relationship is a gross generalization. Many people (men and women) are firmly planted due to children, jobs, etc. While it may not be your preference, it’s a perfectly acceptable reason not to start a relationship if that is someone’s priority. For your sake, I hope you find someone with her bags packed!

      Best of luck,

  5. I wrote one and find that I want a permanent relationship with someone to hold my hand & have easy conversation about his life before me & our dyn-o-mite relationship now

  6. I’m 70 and am looking for someone 50 to 60. I never look at profiles of women under 50. I’ve been writing someone for well over a month.. We seem to hit it off incredibly. She admitted today that she’s 42 not 54 and has a 14 year old son. I’ll admit that I am crushed. I’m an old fool! Is there any way, short of asking for a birth certificate, to check this out.

    1. Leonard,

      First, I do have a comment about the age range you’re looking for. Why not expand to women your own age? It’s important to think this through:

      Now, for your question, it’s certainly rare that a woman for like about being *older* than she is! I would set up a meeting over coffee. And if that’s not possible, Facetime or Skype. In the end, age is just a number. If there’s a connection, it’s worth exploring.

      Thanks for reading,

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