Should You Go on a Second Date_Ken Solin Header

Eavesdrop on people talking about their new love interests and you’ll likely hear a laundry list of what’s wrong with the people they’re dating. While there’s no magic to prevent this, those lists can be shrunk and sometimes eliminated. A second date should depend on whether your date on the first one exhibited a fair amount of relationship potential, and a coffee date can be telling if you know what to ask. I don’t ever consider settling as an option.

The stakes are too high to waste time in a relationship with someone who doesn’t embody all your requisite ingredients. There will be plenty of issues in a relationship that require compromise, but the answers to the following questions indicate basic interpersonal skills. They’ll narrow the field considerably, and that’s the point! Dating smart doesn’t mean kissing lots of frogs. It’s not a numbers game.

People out of long-term relationships may feel date-rusty and find it difficult to decide if a second date is warranted. And a dating dry spell can contribute to fantasies and projections about a first date based on little information, a lot of hope, and a powerful drive to be in a relationship again. The answers to these five questions relate to relationship potential, and this isn’t a best three or four out of five either since they’re all reasonable.

The ability to identify appropriate dates is worthwhile. Virtually any man or woman who has done some amount of inner work should be able to answer these questions handily. Your success depends on dating smart, and this one way you can be your own best friend.


1. What’s Under The Hood

Has your date done any type of personal growth work, individual or group therapy, been in a men’s or women’s group, attended any workshops or lectures about personal growth or relationships, read any books or magazine articles about relationships, or done anything at all that indicates an interest in co-creating a successful relationship? This is critical since every relationship runs into trouble, and knowing how to work through it is learned behavior. These aren’t skills that are second nature to many people, but someone who’s done some personal growth work will be reasonably skilled at problem resolution.

2. Friends Matter

Does your date have same-sex friends? This is important because it points to trust, and someone without friends isn’t the best candidate because they likely have trust issues which will show up in a relationship. And dating a loner means you’ll become that person’s entire universe, an onerous burden. Having close friends suggests relationship skills since every friendship faces issues that need resolving from time to time. Remember that the best relationships are also the best friendships. Knowing how to be a best friend takes a willingness to trust and be trustworthy.

3. Boring?

Did your date show interest in you and your life? Did he or she ask you a fair number of questions? A frequent complaint is a first date that didn’t stop talking about his or her life and failed to ask their date anything about theirs. This is a red flag because it suggests a self-involved person, and self-involved people don’t make good partners for obvious reasons. There are no excuses for rudeness, and a second date will only confirm that this date wasn’t a good prospect.

4. Generosity? Maybe Not

Does your date have some means of support? Unless you’re okay with financing the relationship, this matters. And, the inequality of lopsided financial relationships rarely works. I’ve noticed too many relationships based on one person supporting the other, and few worked out. This is in part because there’s nearly always a quid pro quo, whether verbalized or not. This doesn’t apply to married couples, but in general, there’s no free lunch.

5. Hot Or Not

Physical chemistry is vital, although I’m not suggesting sex too early in a relationship. Not becoming sexual until both partners feel confident the relationship is viable makes sense. This helps avoid the hurt feelings that accompany a rocket ride, a failed relationship that became sexual before both partners’ feelings were clear. A satisfying relationship embodies a powerful physical chemistry that’s usually obvious from the start. Don’t sell physical chemistry short. It’s too important to simply hope for the best. Relationships are difficult enough without becoming enmeshed in one that lacks passion.


If you’re skeptical or shy about asking these questions, think how you’ll feel after wasting months with someone inappropriate when you might have discovered their issues simply by being up front and honest. Whether or not to have a second date will be much clearer. The only people who might find these questions objectionable are likely those who can’t answer them well.

Of course there are other factors involved in determining a first date’s second date potential, and these questions certainly aren’t going to work perfectly every time, but asking them beats throwing darts at online photos.

Ken Solin is a dating expert for , and writes about sex, dating, and relationships for He has worked with men in groups for thirty years, helping them to move beyond the issues that prevent them from enjoying successful relationships. Ken is a father, grandfather, and an entrepreneur living in the San Francisco Bay Area. His book, Act Like a Man is available on Amazon; he also just completed his latest book, You Gotta Have Heart-To Meet Your True Love Online.
  1. Love #1.

    But disagree with #2. As long as a person has good friends, why must they be same sex? Many same-sex friendships between unmarried women can be competitive (sad but true), so to make the “same-sex” part of it a requirement is unfair. As long as people have outside friendships, the gender of the friend should not matter.

    #3 absolutely.

    #4 is odd as many people will have a relationship intending it to lead to marriage so … “this doesn’t apply to married couples”? .. not understanding this.

    #5 yes.

  2. “The stakes are too high to waste time in a relationship with someone who doesn’t embody all your requisite ingredients.”

    C’mon! For a GD second date???? Nothing like pressure for an already-neurotic breed of humans.

  3. “And dating a loner means you’ll become that person’s entire universe, an onerous burden.” — This seems a “bit” judgmental and condescending or was this a typo which should have said, “And dating a loner *may* mean you’ll…” Otherwise, nice article.

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