Should I Give That Guy One More Date?

A few weeks ago I wrote a post about chasing vs. pursuing.  I’ve already decided we need some new language to make all of that more clear, but that is not the topic for today.

I received a note from one of my female leaders asking a good question in response to that post.  In actuality she asks a much more important question, perhaps without knowing it.  I don’t typically write specifically to women here because, well I’m not one, and I don’t come from that experience.  But I think this is important and merits an post.

Her question

In follow up to the post on chasing vs pursing, may you write a refresher on how women should appropriately response to being chased or pursed? I think that for the well liked, popular Christian single lady, it may be easier to differentiate the two and act accordingly, perhaps due to exposure or experience. For other women, especially when requests and invitations are few and far in between, or even non existent, it can be hard to tell what is a good and noble pursuit versus what is simply a chase because we are a woman. Sadly, I have fallen for this one, and I would appreciate insight on how a woman should respond to such encounters in the future.

This question brings up a few very important points that we need to consider.  So let me take a crack at them here, while hopefully helping answer the intent of her question.

I think what she is really asking is not so much how to understand the difference between knowing when guy is chasing vs pursuing, but instead how to know who to respond to. How do you know who is noble regardless of their approach?

This is a vitally important thing for women to get a hold of.  Because here is a gigantic truth.  Ok ready?  Both noble and ignoble men can be chasers and both noble and ignoble men can be pursuers.

This is what I’ve been telling men here for four years.  Being a good Christian guy or even being a guy who would make a great Christian husband does not necessarily help you attract the girl you want.  It doesn’t hurt, but it’s not typically what causes or doesn’t cause attraction.  It doesn’t get you in the door – it should help you seal the deal.  It’s the difference between marketing and managing.   Two totally different skill sets.

In the Church we only teach one skill set – that’s being a married person. It’s killing us.

So let me actually answer the question as best I can for the ladies that are interested out there.

First, you need to understand that initial attraction, while nice should always be checked with some qualifiers.  Now that doesn’t mean you have to figure out all the qualifiers before you go on a date.  But it does mean you are looking for some things. And you are looking for them quickly.

I say quickly because if you let attraction grow with someone who isn’t qualified you can end up in a bad spot in a hurry.  Pretty soon you are saying things like, “I know he’s not a Christian but I can’t help what I feel“.  Bad.

What you need to have clear in your head is that for most women, what is attractive about a guy initially is how he carries himself, how he talks to you, how he “makes you feel”. Again there is nothing wrong with feeling attracted, even to the “wrong” person.  But that attraction does not make the guy noble or not.

There are a lot of guys who would make great husbands who come off less attractive at first.  But if you want a good marriage, then you need to think about not just how you feel, but what kind of man this guy is.  Is he deep?  Does he lead others?  Is anyone following him?  Do people respect him?  How does he treat people?  What does he do with his time and money?  Is he a hard worker?  These are all good questions that show you more about him.

A great example happened recently to a gal I know pretty well.  She came to me after being on a few online dates. She said that one of the guys seemed like a really good guy, with a really good background.  She “wanted to like him” but she didn’t “feel” that attraction.  Now realize this is after one, maybe two dates.  She asked me what I thought.

I said, if you want to get married then I would maybe give this guy another couple of dates.  The truth is that a lot of Christian guys aren’t super comfortable and confident right out of the box.  There are many reasons for this (which we’ve talked about ad nauseam here) but if you think he is a high quality guy, then I’d give it another go.

She did and they are well on their way to marriage.  As they dated more, he got more comfortable and therefore she grew more attracted.

Now that won’t happen every time.  I’m not suggesting here that you marry someone you aren’t attracted to – although you could.  What I’m saying is that how someone pursues you has to do with attraction, not how noble they are.

Bottom line, if a good guy seems awkward at first, I’d give him another chance.  See if after a couple of dates you feel different. If he stays weird then yeah, maybe you bolt.  And if a guy charms you and you are paying attention and figure out that he isn’t a good guy, forget what you “feel” and bolt.  In a dream world, you are instantly attracted to a good guy.  But we live in the real world.



11 thoughts on “Should I Give That Guy One More Date?

  1. The game (for lack of better term) changes for men and women……especially the “never married Christian single” as they age. We are held to standards that are way above and beyond the world’s view. It’s not easy. Secular culture has not only been welcomed into the church, but it has now taken root. In too many cases, accepted as “normal” behavior.

    Women have to be careful; because for the woman who “always” was asked out at twenty and had a few dates a month at that age….by her mid-thirties she usually is down to maybe a dozen a year….and by her forties she might have a one or two a year…….

    Don’t cut the man off at “one” date. Especially if you are into your forties. Now, if he behaves in a very boorish and un-Christian manner. Sure. Drop him…..

    Otherwise, accept that the “game” has changed. Not by you, or the society at large….but due to the plain fact that you are “just older” now. You should have a “tad” bit of wisdom from your Christian walk that demonstrates your faith, walk, and what you thought you wanted at 25 isn’t what you want at 45 *in your situation now*. Justin has mentioned several times that being married for the first time in your forties *isn’t* the same as being married for the first time in your twenties. It isn’t. You cannot compare, or expect that. The same should be for dating. A Christian woman dating or trying to meet a future husband in her forties cannot; let me say this again, CANNOT make the date a job interview. You know…”So what do you do, why don’t you have a house, you’re nice….tell me why you never got married…love ’em and leave type……..where is your car…where do you see yourself in five years. What are your objectives. Have you thought about going back to college for a better job?”

    The guy may indeed drop you for future dates. You’re in your forties now. It’s okay. You both have been around and seen a lot by this point. The goals, and expectations will come in a few dates. It’s not a race. You waited long enough for a husband, just enjoy few dates with a man for what it is. A date. You want him to lead? Then let him lead, and not by “conditions” of what you determine what leadership is to you at that moment. Leadership is a loaded word. Everyone wants to be “the leader” but I have witnessed very little leadership from self-proclaimed “leaders” (men and women) in my walk in life.

    Plenty of Christian men (speaking for myself here) don’t have a clue here and we can go on and on for the next decade about “what we should have been doing all along” but remember too; they might have had some hurts, bumps and scrapes along the way too with Christian women. No man is going to Jesus, and soulmates don’t exist. You’re both pushing into middle age now. The game has changed. Clean slate. Time is on the plus side now……erase the board. Start fresh.

    Men have to understand at this age that no woman in her forties is going to look like she did when she walked on to campus in 1989. This is a fact. Single Christian men at this age need to start fresh as well if they want a wife at this age. Erase the board. Start over. You don’t have anything to lose in your forties concerning asking a fellow Christian woman out. Sure, at 20 it’s nerve-wracking and it can be heartbreaking, destructive to self-esteem, but now…..if she says “no” well, so what? Leave her alone. Watch and wait in a Christlike manner when you are ready to ask someone else out. Sometimes solid discernment is the overlooked aspect of leadership, even in church. Men have to pursue, I understand that….but if the woman doesn’t want to be pursued by you, or let you attempt to lead? Don’t waste her time or yours. Be polite and keep moving.

    Since I am single and not married….and I hear DAILY advice from Christians who are married about being single, I have figured I have my opinion counts just as much concerning these matters. I have no idea “what women want” because everytime I get advice, I witness the opposite behavior for countless people. Dating is just subjective in these matters. A woman likes you or she doesn’t. A guy likes you or he doesn’t.

    Every generation when they come of age thinks they will be the first one that stays eternally young and has all the time in the world. The wisdom we have in our forties now should actually help us at this point with meeting someone……..if you want to be married. Drop all your misconceptions about the opposite sex because obviously they were wrong.

    Great post Justin

    • This situation came up for me recently when I was set up on a blind date with a guy who from all viewpoints, seemed like a great catch. Although we didn’t click the way I had hoped, I opened myself to going out with him again. Turns out, he was the one reluctant to pursue a second date because he didn’t see much interest from my side (despite the fact that I tried to be engaged (laughing, smiling and participating in the conversation) and open minded). I texted him a thank you note and told him I had a good time. According to the couple who set us up, he’s got some confidence issues which is probably something I sensed and why we didn’t initially click. At the end of the day, there are personality types that work together and others that don’t. Men who have confidence issues typically don’t ask me out so any decent man gets points just for making the effort.

      While I’m on the subject, I see men, including on this site, complain about women’s preferences for tall men and how it shouldn’t matter how tall a man is. Well, I’m a tall woman and I can tell you that men make it very clear that they have height issues as well. They very vocally complain when I wear heels – even the men who are married and shouldn’t care. It’s super annoying because I like to wear heels, so I hear it all the time. One guy I met online asked me how tall I was and being allegedly 2 inches taller, he said he wasn’t sure if he was comfortable with that. Too be honest, I was glad he said it first. Yes, I prefer tall men too, but I think men complaining about women’s preferences should be honest about the fact that men have height preferences too.

      As for being older, keep in mind that not everyone ages at the same rate, as well as some younger men are attracted to older women, so being a single woman in your 40s isn’t necessarily a liability, I have a friend who married for the first time at 45 to a man 11 years younger than she. I have another friend in her mid-40s engaged for the first time to a man 8 years younger. I’m also a much better dater than I was in my 20s, and much more confident, so I have higher hopes than I did when I was allegedly a better catch.

      Finally, my faith that God is going to lead me to the right guy is much stronger than it was when I was younger – and yes, I don’t need reminding about the non-existence of soulmates – but a guy out there is right for me. I only need one.

    • I dont know any Christian women in their 20’s who have been asked out on a dozen dates a year, I don’t know any Christian woman who have been asked out on a dozen dates in a decade. Unless, you are counting the non-christian guys who ask them out. I know attractive, personable Christian woman in their mid to late 20’s who’ve never been asked out by a Christian guy ever.

      • To subjective to reply fully to that comment. I could easily turn that around and say “I know plenty of handsome, polite, attractive Christian men and every Christian woman they ask out says “no” or tells them that “Jesus is their boyfriend right now”

        We have a problem in our church culture, and both women and men are to blame for it and it’s sadly not going to get any better in the near future.

  2. I never said it was a “liability” to be a single woman in your forties. I am a single man in mine and facts are plain: I can’t ‘keep up’ with a man who is 26, fresh outta grad school with a full-head of hair and just has “youth” on his side. It’s unfair a bit arrogant to think that I can; and men who pretend they can with their “confidence” look pretty silly.

    The game has changed that’s all. I didn’t say it was “over” nor did I imply they was “no hope” but in your forties as a Christian, and a single…..and if you indeed want to be married….the game changes. Sure you may have a guy who falls for an older woman……but it’s not common.

    I mentioned offhand once offhand at one of our church potlucks that “I could date a woman younger than me”

    Pastors wife heard what I said and spoke up “Brother, you should be looking at women your own age, plenty of single mom’s in this church need a man. I don’t know what’s wrong with you men all wanting a woman younger than yourself.”

    She assumed I wanted a woman who was twenty or something. I know better. Totally OUT of my league btw, and creepy if truth be told. Sure, five to seven years younger……five to seven years older…..fine.

    Look, I don’t know you and I mentioned “soulmates” for the fact that YOU may not believe in them as well. Applause, and I meant zero offense. However, WAY too many Christian women DO believe in them.

    I liked your reply, and I hope you have a good day!

    • Thank you Jason.

      I agree that the game has changed, but it’s just different – not better or worse. I think most of us who have been single for a long time have done extensive soul searching into why we’re single for so long. For me, I’ve done my soul searching and made some changes in my attitude and approach (in life, in general).

      For being in your 40s, or anything else for that matter, I think you can stand on your own merit. You can still have confidence in what you bring to the table and it’s not arrogant to recognize that.

      I think this all has to do with perspective. Is dating in your 40s a glass half empty or half full?

      I agree that there are some major issues with our church culture regarding dating, but I don’t think it has to get worse before it gets better. We’re trying to make it better now by having these conversations.

  3. “confidence of what you bring to the table”

    There is a very fine line between confidence and arrogance, we Christians actually have an advantage over the “secular world” because we know from our beliefs about true humility, repentance and rebirth. These factors right here should be helping us in our discernment of what “confidence” means and what it really is.

    Do we practice this in our dating lives? No, we don’t. We have dragged the secular world’s view of what “confidence” means into church culture. Accepted it, and then juiced up with Christian theology and “christianized it” and we wonder why men in Christ are failing terribly at this when it comes to dating, and trying to be confident. Our confidence looks like a cheap piece of IKEA furniture. Looks great in the store, fun to put together…then when applied to real Christian life (dating and possible marriage)….it breaks and falls apart. Fast. We got what we all supposedly wanted in church-culture. What was fun and cool a few months ago; we’re now trying to ditch or pawn off on someone else (blame). This ties into SO much today in church communities….and we all wonder why men don’t come to church, spiritual growth by women turns colder as they age alone, and teens as soon as they turn 18 and go FAR away to college ditch church……

    Sorry, I ramble….

    Ah, yes! Confidence. We all have been told that Christ was confident.I agree. Christ though was confident in what he brought to the table. He didn’t have to be “proved” in all areas. He didn’t have to explain or tell people “why he was confident” or “how smart he was” or prove it in the looks department (according to the Word, he was just a plain looking man) about His confidence there. He didn’t even have a real job for the three years of His earthly ministry (in today’s church culture, he would be called a bum and freeloader from too many pulpits in conservative, “bold” evangelical churches for that matter). His confidence was in His Father. His mission, and the news He proclaimed.

    It wasn’t material possessions, or a cultural lifestyle… was standing firm in the Father.

    In my men’s fellowship, the one pastor likes to talk about how “bold” Jesus was about “getting what he wanted” (He uses the worn out “Jesus turning over tables and equating that to real manhood” analogy).

    I just see a sorrowful Savior, who washed His disciples feet, openly wept for His friends, wept for the Jews and paid the price CONFIDENTLY of what he stood for.

    This topic needs to be dug and really opened deeper than just by men like me (who am I?). The right man who is articulate or charismatic and is a solid believer could really do wonders for this….

    But I am “confident” that the confidence we push on men in our church-culture today, and right now……..isn’t working. Would you as a sister agree with this???????

    I like this banter btw, and thank you for your reply above

    • You’re welcome. I think conversation helps.

      My definition of confidence includes the man (or woman) who may be plain looking, but still is secure in what he brings to the table. It’s not about how much you have, but about the assurance that you’re “enough” regardless of what you have or what others say about you. It’s the understanding that you don’t have to prove anything. Confidence falls all over the attractiveness, intelligence, education level, career spectrum. I know some very confident people who don’t meet certain superlatives, and honestly, confident people make the best friends and colleagues because they’re not busy trying to put you down – they’re just living life. Arrogance is thinking you’re better than everyone else. I don’t think they’re the same thing.

      As a woman, I like to think of “boldness” in Christ too. Christ gives us confidence and encourages boldness. I can see how men are beaten over the heads with the idea that they have to fit into a proscribed definition of manliness, but people can confuse that definition with confidence and it’s not right.

  4. eh…that’s just having a thick skin, by not caring what people say think about you or what you have / don’t have……arrogant people have that too and actually practice it better than confident people….

    this is where it IS a fine line.

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