Dear Michele: How to Make the First Move?

Dear Michele,
As a guy, I’m totally confused on how and when to make the first move. And how can I make it clear that I’m interested in pursuing a romantic relationship (in stead of “just friends”) without seeming too pushy? I hear women talk about “that guy” who is all over them, and I don’t want to be him, but I think sometimes I end up waiting so long to make the first move that the woman has “moved on” because she didn’t think I was interested. What’s the right balance? How do you approach a Catholic woman?

Signed,
How to Make the First Move

Dear How to Make the First Move,
Thanks for your question, because I get letters all the time wondering exactly how to let a woman know you are interested. I can understand the challenging being is anticipating the perspective of someone you don’t know. So, what can you do? There are several possibilities.

If you are on a site like this one, when you find a profile you like, you can send her a “smile.” It’s the perfect way to invite her to look at your profile, and then if she’s interested, she can respond. If you don’t receive a response, one short email asking her to read your profile and then get back in touch if she is interested would be appropriate. This is a dating site, so chances are pretty high that a woman would understand that you are interested in a romantic relationship. In your profile, and in hers, you can list if you are looking for fellowship (friendship) or a soul mate, or something in between. That’s the wonderful part about this site, it takes away a lot of the guess work.

Ok, so now you are communicating via email. My advice is after 3-4 email exchanges at the most, set up a time to talk on the phone. You don’t want to establish a relationship over email, you just want to determine if she is interested. If she responds to your email within a day or two, with descriptive answers, then she is interested. When you do move into phone conversations, don’t get caught in the “phone trap,” where you are having lengthy conversations without moving to the next step. If you live within a few hours drive, I would suggest that it’s appropriate to ask for the first meeting at the end of the first or second phone conversation. You may talk several times before actually meeting, but to let a woman know you are interested you need to move the process to the next logical step.

I think sometimes Catholic men tend to want to be too “nice.” It’s ok to be interested, it’s just not ok to be pushy. What’s the difference? A man who is interested shows his interest by asking for the phone number, or the date, and then respectfully accepting the answer. The pushy guy follows up with a “why not?” or “what are you afraid of?” If you can’t ever see yourself asking those types of questions, then you’re pretty safe that you will never be “that guy.” What you risk in being the “too nice guy” is that you send a mixed message, and the woman on the other side is never quite sure if you are interested.

What if you are not on this site, and you meet someone in church or out at a social gathering? You can show your interest through your time and attention. If it’s a setting where you think you will see the person again (ministry event, work event, friend of a friend), then introduce yourself and have a casual conversation. If you don’t feel comfortable asking for a phone number at that point, then the next time you see her, make sure that you stop and have a conversation. Don’t let an encounter go by without some direct conversation, one-on-one. And give her your undivided attention. She will know that you are seeking her out, and after the second or third time (at the most), I think most women would expect you to ask for her number, or ask her out on a date right there. The reason you give your attention is not only to show your interest, but to discern if she is interested in you. If she stops and talks, without making an excuse to “get away,” then she is likely interested.

When women ask me, “how do I know if he is interested?” I always respond by saying, if he’s interested, he will ask for your number. And he will call. And he will ask for the date. And he will ask for the next date within a week. So, if you are interested, pursue. It’s ok, if she is not interested, then it is her responsibility to communicate that to you. If you are not sure, you can always simply ask her. We are adults, and if a potential date can’t respond in a mature manner to your interest, then that is not someone you want to try to date.

And to the women: if you’re not interested, don’t play games. Just politely tell him. Please, make it easier for the woman that may be interested. Don’t send mixed messages. If you don’t like him, don’t give him your number (or a fake other either). Simply tell him that you are not interested, or you don’t see it as a match, whatever is easy for you to say naturally. Don’t add to the stress of dating by trying to be “too nice.”

I hope that helps, and I hope it encourages you to respectfully pursue when you are genuinely interested.

God Bless,

Michele Fleming, M.A.