Dating An Old-Fashioned Guy (15 Things To Expect)

If modern dating is all you’ve ever known, being with a man who leans towards the old-fashioned way of life can be… new. Unlike the former (which, like almost everything else these days, is driven by instant gratification), an old school man can wait in a dating relationship.

In a society where most people want to enjoy the benefits of a relationship with little or no responsibility, dating men with old-fashioned values can be a refreshing change of pace. Unless you prefer non-committal, casual relationships, or consider yourself a non-conformer, in which case you should probably stick with the modern dating scene.

Since you are here, I assume you are already considering a man with old-school preferences. And though I can’t categorically say how your relationship with men with such inclinations will turn out, I can tell you a thing or two to expect. Read on.

15 Things To Expect When Dating An Old-Fashioned Man

1. He will want to wear the pants in the relationship 

Men who prefer the dating style of times past often have the desire to lead in a relationship in common. And while I’m aware of the sexist undertone, many of them aren’t that way because they think a woman cannot take the lead, too.

Instead, they do it because it comes naturally to men to take initiative, and leaning into those roles brings out the best in them in relationships. And no, this doesn’t translate to him doling out orders while you, his woman, timidly obeys every word, either. It just means he’ll readily take on responsibilities of the man of the house like initiating conversations and tackling challenges. 

2. Gender norm leanings

As you can probably already tell from the previous point, old-fashioned men are often partial to the traditional stereotypes about how men and women should behave. While it may not be fair to put them all in a box, you shouldn’t be surprised if he expects or even encourages you to ‘be a lady’. 

He won’t let you split the bill and will readily get his hands dirty, so you don’t have to. He takes these as his role as a man, and in exchange, he might expect you to be submissive, gracious, home-oriented, nurturing, tactful, and other qualities culturally attributed to the feminine.

3. Dates over hangouts

Another thing you can look forward to with old-fashioned men is a lot more official dates. Anyone who’s been in the dating scene for more than five minutes knows how our modern men love their hookups. It’s what most of them are looking for, steady knacks and vibes.

However, when he truly likes a woman romantically, he prefers to get to know her first, and dating gives him a proper chance to do that the right way. Also, dates are less ambiguous than hanging out, a testament to where they stand on making their intentions known.

4. Old-fashioned men go all-in when they date

old fashioned men go all in when they date

He pulls all stops when he pitches his tent with you and might expect the same of you. Flowers, serenades, apologizing with gifts, sending a dress along with the invitation, we all know these guys are the best in the wooing business. 

They usually don't date for fun, so if you go out with one, you can expect him to commit to you and your relationship. Often right from the moment, he realizes he likes you. But that it happens quickly doesn't mean they are fickle. Men with old-fashioned values are some of the most detailed oriented folks you'll ever meet in the dating scene. 

Before he even approaches you to ask you on a date, he must have done his homework and be convinced to a reasonable degree that you're it. 

5. May not kiss on the first date

Even when there's all indication of undeniable chemistry between you and you can tell he really wants to, a traditional guy may not initiate anything physical on your first outing. Because he is a sucker for propriety and wouldn’t have earned it yet at that stage.

More so, they don't take relationships lightly, so when an old-fashioned guy dates, he prefers to lay an emotional foundation first before everyone gets carried away with the physical. And it probably won't stop at the first kiss, you may have to say yes to a couple of dinner dates before he attempts to go to the other bases.

6. Patience

This god-like self-discipline (compared to an average modern guy) that makes them resist going in for that kiss too soon can extend to other areas of their life also. Maintaining composure is something of a second nature to a typical old-fashioned guy. 

He takes his time and doesn't like to rush anything, whether it's fixing himself up or dating. So, you can rest assured knowing he won't pressure you into anything you are not ready for, milestone-wise. (Of course, there are always exceptions so always watch your 20, sis.)

7. Gentleman behavior

The best old-fashioned men to date are the gentleman kind, and thankfully, that makes many of them. You know the type who holds doors, pulls out chairs, lets you go first, kisses your hand, who continues to prove that chivalry yet lives. 

These men have a deep respect for women, and you would see the signs in not just how he relates to you but also with others. You can expect even more queenly treatment if you date one because old-fashioned gentlemen tend to take romance personally.

8. Loves to look good and may expect the same of you

loves to look good and may expect the same of you

You know what they say about gentlemen, they are never caught unfresh. Not every old-fashioned guy you meet will always pull up in a three-piece suit, but you can expect to see a class in whatever they wear. These ones really take the saying about being addressed the way you dress to heart.

He knows how he presents himself reflects on his significant other as well, so you won’t ever have to worry about him embarrassing you by the way he’s dressed. The only catch is, he will judge you by the same yardstick and expect you to be just as interested in looking presentable. 

9. Meeting the family is a big deal

You can’t separate an old-fashioned guy from his family values. Men like this usually hold their family in high regard, especially the one who groomed them. If you’re the type of woman to try to compete with your boyfriend’s love for his mom or sisters, don’t try it with this one, because he most likely won’t choose you.

His root means everything to him, and he will wear that proudly like a cloak. He probably wouldn’t casually ask you to attend a family event with him, let alone meet the ‘rents unless he’s sure. They are that important to him, and so will you if you ever become family.

10. Likewise, his friends

Meeting his friends is, no doubt, an important relationship step for most people, but doubly so for traditional men. This is because they tend to place a premium on their friendships and thus believe those closest to them wouldn’t steer them wrong. 

Now those first few run-ins with his friends are lowkey evaluations. And they usually happen early on in the relationship too, before things get serious, you must have crossed paths time and again with his buddies. If you don’t pass the test, it doesn’t bode well for your long-term compatibility.

11. Marriage

Old fashioned men’s dating style follows a predictable pattern: He likes you, woos you, asks you out, and then arranges a date if you say yes. If all goes well, the first date turns into the second and third… If you agree to go out with him and seem genuinely interested, he may assume that exclusivity is implied and not expect you to see anyone else.

He enters every relationship with marriage and starting a family as the big picture (and typically makes that clear from the onset.) So, if you’ve been dating for a while, you can expect him to pop the question sooner or later, and if he doesn’t, it wouldn’t be because he doesn’t want to get married.

12. Children/parenting style

children parenting style

This may seem like a far cry, especially if you’ve only just started dating an old-fashioned man but while we’re putting things out there, you should know this too. He will most likely want children because as I said, family means everything to this lot.

More importantly, he may opt to raise those kids the traditional way too, with one parent taking care of them while the other works. And unless he’s a mix of modern and old-school, the stay-at-home baton will very likely fall on you as the lady of the house.

13. Direct and clear principles

So no games, you can expect him to communicate his intentions, needs, and feelings as necessary. Usually has and follows a set of philosophies too, about romance, adventure, culture, and life in general. An average old-fashioned guy lives for these things, right after family and country. 

He prides himself in loyalty and not just in his romantic dalliances, but also with his guys. Especially with his guys. All this talk about principles might make these men seem rigid and outdated, but that notion changes when you meet one with no internalized issues against women (sexism, misogyny, etc.).

14. Financial responsibility

You can count on the male ego to keep an average traditional man financially responsible. One of his biggest fears is being in a position where his woman has to get her hands dirty to keep the family afloat. He believes as a man, it is his responsibility to provide for himself and his lady, not the other way round.

He takes pride and strength in his work and takes from his ability to get things done independently, so the last thing he’ll do is willingly walk into money traps. Not if it means jeopardizing his standing as a provider, or worse, becoming a liability to others.

15. Will always do things by the books

Old-fashioned guys aim to be culturally straight as an arrow and are at their best when things go as they should. Look at everything from his obsession with manners and etiquette to never being caught inappropriately dressed to even his approach to relationships, and one thing stands out – order.

A man with such values won’t appreciate seeing the lady he’s dating swear profusely or acting rude to staff because that wouldn’t be proper. He would never raise his voice or hand to a woman, even if it means the end of him because gentlemen don't roll that way. 

And when it comes to love and family, these are the most important things in life as far as he is concerned, so he sees that as even more reason to follow the standards. 


How do you know if an old-fashioned guy likes you?

When an old-fashioned guy likes you, he goes all in. He would approach you and ask you out on a date, take his time to organize them, and treat you to a new romantic gesture each time. Things may be a little slow on the physical front, but that’s because of how much respect he has for women.

What is a traditional guy?

A traditional guy is a man who leans towards the old-fashioned way of doing things from dating to his taste in women and general approach to life. He stays close to his roots and can be a little hard to sell in modern culture.

What does an older man want in a relationship?

An older man typically wants things like stability, companionship, intimacy, and peace of mind in a relationship. At certain ages, dating becomes less about playing games for men and more about the real stuff.

How do you know if a guy is genuinely interested?

Men who are genuinely interested in you can’t do much to conceal their feelings around you. They would pay you more attention, and be more tender and protective of you. You’d know that you are a priority to this person from the things he says and he does.

How do you keep an older man interested?

To keep an older man’s interest, you need to be more than a pretty face. Aim for classy in your dressing, be able to hold an interesting conversation, make him laugh, and bring your youth to the table.

In Conclusion

So, has this list done anything to change your view of dating an old-fashioned man? Remember, everyone cannot fit in the same box when it comes to old-fashioned dating, so if you really want to get to know retro men, the best way is to befriend one. Or a couple, lol. Let me know what you think of the article in the comments and do well to share, if you enjoyed reading it.


Leave a Comment