Dear Cindy ~ Initiating Contact Online

Dear Cindy,

     I am writing for advice. After taking a year off from online dating, I just signed up for Catholic Match. In the past, I did eHarmony and Match, with no luck. I also realized that any time I initiated contact with a guy (a wink or “liking” one of his photos), we might end up messaging, but nothing has ever come of it beyond that. So my online dating strategy has been to write the best profile that I can, then just wait and hope. Most of my friends think this is crazy to be so passive when one is paying for a dating service. Can you tell me what you think? (especially since I’m pretty sure you said you met your husband via Catholic Match)?

 Thank you,

Patiently Waiting


Dear Patiently Waiting,

I believe that the need for the guy to initiate contact is the same no matter whether it is online or in real life.  Maybe even more so and here is why:

The two of you have joined the online dating site for, hopefully, the same reason:  Marriage  If a guy is going to pay money to have access to hundreds (thousands?) of potential wives, it only makes sense that he would be aggressive in his search.  If he is sitting back and waiting for girls to initiate contact, then that, to me, indicates that he is missing one or all of the three R’s.

The Three R’s

Resourcefulness:  He is not very resourceful and this will drive you craaazy in a marriage.

A resourceful man will spend time searching for his love and with online dating, it could not be easier.  It takes his search from several billion (in the whole world) to several thousand (on the site).  And, if it is a Catholic site, his search is narrowed down even more because every single girl is of his same faith.  All he has to do is read profiles, look at photos, send an email and decide if he wants to pursue her.  Easy peasy.  If he considers this hard or too difficult, then this says something about him.  He is not resourceful (read: lazy). A lazy man in marriage is the worst. No, no you do not want this!

Readiness:   He is not ready for marriage and this will drive you craaazy as you ‘date’ him.

Like a toddler who plays with his food by moving it around on a plate, some guys just play with the girls on the site by texting, emailing and even dating.  But, his efforts have no end goal behind them.  It is just something to do until he is ready.   The toddler is not hungry nor does the food on the plate inspire his taste buds.  Same with the guy who is on the site but is not ready for marriage.  He is not hungry nor is he incentivized to seek out someone to satisfy his hunger.

Realistic:  He is not realistic and this is a huge turnoff.  Or, it should be. Some guys see online dating as a source for young, perfect and holy women to pick from. They are hoping for girls who are, dare I say, out of their league.  For example, he is 45 and his filter is for girls age 20 – 30. He is not attractive yet he only initiates contact with the girls who have many guys fighting to get their attention. The problem is he has not properly assessed himself. He is just not realistic.

He Picks You, Then You Decide

A man who is resourceful, ready and realistic will use the site to his advantage to successfully find his wife.  He knows himself well enough to know who he can attract and who, most likely, will not be interested in him.  This man will make you feel cherished and pursued.

Once he picks you, then you are in a position to decide if he is right for you.  It is a horrible feeling to “pick” a guy only to have him decide against you.

The Problem With Female Initiation

When girls initiate contact online, they feed the beast and they weaken his resourcefulness.  Like a toddler, he feels justified in playing with his food (you and your feelings).  Besides, he didn’t even have to get up to put the food on his plate.  It just arrived. And he wasn’t hungry.  In his mind, this is not his fault!

A wink or a ‘like’ seems harmless and maybe it is.  But, would you wink at a guy in real life just out of the blue? It puts the guy in the role of the pursued rather than the pursuer.


Finally, when girls initiate contact, it prevents the man from assessing himself truthfully.  It makes him think that he can get a girl without even trying and that he is highly sought after.  This is not good for him nor is it good for your sisters in Christ.  Rather than being humble and realistic, he is full of himself.  Rather than pursuing a sister in Christ and marrying her, he is stuck in fantasy land because you have contributed to the trend of female initiation.

Let Him Suffer Through It

There is nothing better for a man than solitude and honest introspection. It is good for him to take risks and it is good for his future wife as well.  He will always think “I did it! successfully wooed her! Isn’t she amazing!”  It is good for him to exhaust himself in his search only to finally find the pearl of a great price.


I kid you not, this superabundance thing is your secret to attracting your husband.  The supernatural power of Chastity makes you like a magnet for the right guy.  Keep in mind that there is physical Chastity (the right application of our bodies and fertility) and emotional Chastity (the right application of our emotions).  Let’s add one more:  Behavioral Chastity.  This could be described as the right use of your mind, intellect and actions.  This includes not allowing yourself to believe that you have to compete as if you are ‘of the world.‘  No, you belong to the Lord and you must think and act in accordance with that belief.

It Is Not A Competition

God’s will does not require you to compete for your husband.  You will not need to become the aggressor in order to get your man’s attention.  Your Father in heaven may be saddened at the idea of his precious daughter acting like you have to control something that is not yours to control.  You can trust in the Lord.

Go here for more online dating advice: Mr. Online Man

God love and bless you!

p.s.s. Check out all my posts listed by category here!

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18 thoughts on “Dear Cindy ~ Initiating Contact Online

  1. Pingback: Analyze This, Over-Analyze That – Becoming Perfectly Myself

  2. I agree with this Cindy. However, what is your opinion on extroverted women initiating contact in real life with multiple men as part of being social or mingling? Is this out of bounds or if done with mostly platonic/ fun intentions – pretty okay?

    • Hi,
      I think it depends upon what you mean by ‘initiating contact’. Do you mean that you call these men and invite them to social events? If so, then again I think it depends. If you or your close girlfriend are hosting the event, then sure, initiate contact and invite men. But, if not, then I think too many of these invitations (to a ball game, a movie) can make it a little too easy for men. If you are socializing with a man who is interested in you, then he will want to get your attention and let you know that he has set you apart from other girls. Now, you say you are doing it for mostly platonic/fun intentions and if this is true then I think it is fine. Please write to me anytime. Blessings, Cindy

  3. Pingback: When He Writes, “Feel Free to…” | The Veil of Chastity

  4. I too am back in online dating after several years’ hiatus and find it VERY confusing to navigate. This post confirmed a lot of what I thought. . . and I gladly will read anything else you have to say on the subject!

  5. A very reliable, smart, Christian, married man friend of mine insists that women should have very brief, consice profiles for online dating. You may be very proud of your accomplishments, promotions, that you’re a partner are your firm, or the author of a book, but, he says, this is too intimidating. Let them learn that impressive stuff AFTER he’s met you. (Let’s face it, most men are lousy spellers, so if you’re a book author, that’s intimidating.)

    In his words … “The only things a guy on [dating site] should know about you is that 1. you’re single 2. you have a job 3. your profile pic is recent and accurate.”

    Sure, this means you have to weed out a bit more, but you can’t weed if nothing’s in the garden, I guess.

  6. I think you are right, Cindy.

    I don’t do online dating, but I keep hearing about men who are in their forties or above who will not consider dating someone their own age. Look, if you are a man who is 40 and you think you have a chance with a 25-year-old, you don’t have a grasp on reality. I’m a 24-year-old woman. Women my age who are attracted to men that much older are the exception. I mean, if I were a 40-year-old woman, I would never expect men in their 20s to be attracted to me. It’s not impossible, but come on. I’m not Sofia Vergara, and chances are that Mr 40 is not George Clooney.

    Recently my 18-year-old sister and her friend (also 18) have both been unwelcomely pursued by the same 36-year-old man. He has three children by three women, and also has a live-in partner. (N.B. He is not Catholic, and they did not meet him through a dating site or church or anything.) This man is an example of a man who is totally lacking in self-awareness, and who does not have a concept of reality. He also lacks the ability to reflect on how he might appear to women HALF HIS AGE. I don’t know how one ends up in his 30s without those abilities, but it needs to stop. It is officially creepy.

    If a man cannot be attracted to women his own age or thereabouts, he needs to seriously consider not trying to date.

  7. I’m not currently doing online dating though I still have a profile but I always felt weird about waiting to be contacted like I was wasting money but this post really put some things in perspective for me. I’m not ready to jump back on that bandwagon but if I do I have a little more knowledge to work with. Thank you for all your writing.

  8. I NEEDED this! I always worried that I was too passive online but the few times I initiated contact, it never worked out!! Even at a recent singles conference, a man said that on AveMariaSingles, the man decides to pursue. It stung a little because I wasn’t being pursued by the men I was interested in, but it made sense. Welp, I’ll continue waiting…

  9. Cindy!!! Thanks for the great advice – sometimes it’s frustrating being in the middle of the waiting game. I am so appreciative of the kind, supportive words you provide – thanks for allowing the Holy Spirit to work through you!

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