Q & A Wednesdays: How many dates should I go on with Mr. Ho-hum?

Posted by in dating after divorce, first date success, love after 40, online dating after 40, single women over 40 | 0 comments

Dear Sandy,

I went out with a guy I met on Match.com last week. He was sweet, the conversation went ¬†pretty well, and he seemed to enjoy my company. We have some things in common, such as living in New York City during our twenties. But I’m not sure how compatible we really are. I feel like I need to give him another date or two, but I’m just not sure if it’s worth giving this ‘ho-hum’ guy another try. What are your thoughts? Should I cut loose now or give him another shot?


Dear Erica,

Knowing how long to give a person before moving on is one of the toughest things about dating. Especially for women. We want to give people the benefit of the doubt. We feel it’s wrong to judge someone too harshly before getting to know them.

And while I encourage you to continue being open and kind towards your dates, it’s also important not to waste time when you know things are not clicking.

If you had told me that the conversation was dynamic, but you weren’t physically attracted, I’d tell you to get to know him a little better and see if the attraction grows.

It sounds like your date was not exciting, and no real connection was made. All you need to do is follow these simple steps to know whether to stay or go.

The “Three 5’s” Filter

1. List your top 5 values. List the top 5 relationship values that are most important to you. Some examples are: financial responsibility, living within your means, agreement on religious values, where you want to live (country life/city life), parenting style. If you end up in a permanent relationship with a guy, it’s critical that you share common values in order to have success. Find out what his relationship values are early on in the relationship by asking questions.

2. List your top 5 emotional needs. To make sure your emotional needs are met in a relationship, it’s important to identify what they are. Here are some examples of emotional needs that are important in a loving relationship: Being cherished, understood, nurtured, connected, intimate, kind, affectionate, stable. Use your gut responses to your own emotional needs and make a list. See if your date has potential to honor those needs.

3. List the 5 things you can’t live without. This is the non-negotiable list I’ve often written about. What are the five qualities you MUST have in a man in order to make it work? Some examples are: compatible sense of humor, grounded, cultured, well-read, passionate about life. After each item on your list, ask yourself, “Why is this important to me? Is it imperative that he has this quality?” Make sure your list doesn’t include things you actually could live without. You don’t want to narrow your chance at finding love because you’ve included something that actually is negotiable.

Erica, if you’ve completed your three lists of 5, you should have an easier time deciding if your date is worth another chance.You just need to go back and check your list after each date. You’ll quickly know whether to give the date another chance or to move on.

It’s important to spend time developing relationships that have potential. It’s equally important to move on from relationships that are merely a DETOUR on your path towards real love.





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