How to Get Your First Girlfriend at 40 (5 simple steps)

May 7th, 2023

If you're around 40 and have never had a girlfriend- this post is for you.

I reached out to a dozen guys on Quora and Reddit who were in this same position and overcame it. We discussed what the biggest challenges were for them personally, and any advice they had for others in a similar situation.

One person in particular, going by the name of Aaron, helped out a lot and contributed to most of the information I've included here.

Circumstances that lead someone to be in this position can certainly vary. So, we put together a guide with actionable steps for getting yourself out on the dating scene and finding someone special.

Similar principles apply to whether you're getting your first girlfriend at 20 versus 40, but with some more circumstancial relevance.

If you need any help or advice, I've included at the end where you can personally reach out to either of us (you can also just leave a comment).

How to get your first girlfriend at 40:

1. Set Yourself Up for Success

From the wise words of the New Radicals- you only get what you give.

The exact course of action you should take will relate to your level of commitment. Specifically, whether or not you should put significant effort in improving your appearance (either doing so first or alongside it).

We'll get into improving your appearance into the next step, but it may be better for some of you to invest time in the gym first. Losing (or gaining) weight can be incredibly difficult, so remember it's better to whole-ass one thing than to half-ass two.

It's your call. You should still have success either way, just to some different amount or degree.

2. Make Sure You Look Your Best

Aaron said he didn't particularly do much to improve his appearance initially. Still, after doing so, he had substantially increased his success with dating.

You should expect to meet women at the same level of attractiveness, if not a bit lower, than you. Since experience is invaluable for someone in your position, you may want to go even lower.

This is why looking good enough is so indicative of your success.

If you would rather just get yourself out on dates as soon as possible, that's still okay. Here's a checklist of quick changes or updates you can make to your appearance:

  • Hairstyle: The best type can depend on your facial structure. In general, keeping the sides short typically looks best.
  • Style of clothes: If unsure, returning to something simple but sleek is ideal. It doesn't need to be more complicated than a quality pair of jeans and a plain colored shirt.
  • Fitted clothes: This is possibly more important and commonly missed than the style choice itself. Always at least try on the size above and below when buying.
  • Beards: This may mean growing one or just better maintaining it. It's difficult to say what will work best for you, but a barber should be able to help you out with that.
  • Tan: It may not be practical or healthy, but it dramatically improves anyone's looks. "If you can't tone it, tan it."

We'll go into a bit more about this in step 4 when we talk about going on dates.

flat design image of a man getting a haircut

3. Choose The Best Method for Meeting Women

The best method for you to meet women is likely to be through online dating. It's what Aaron used, and it's something that's going to be the best investment of your time regarding the consistency of the results.

Pictures are everything, which means appearance is everything.

However, a benefit you can take advantage of is any career success or even wealth you may have. The point is not to give off some flashy image that you're loaded but that you've got your life together.

Maybe you have a picture of yourself with colleagues on a business trip, in your nice car, or outside your new home, etc. Ideally, be more subtle but still give off the look that you've got things figured out.

I highly recommend getting help with your pictures/profile from any female friends you may have if you're a bit lost.

It's best to keep the rest of the details fairly straightforward. There's no need to overthink how you message others or what you put in your profile, either.

Aside from the pictures, playing the numbers games and using more than one app/site is crucial too.

4. Go on Dates (and Not Stress About it)

There's a reasonable chance women around your age you'll meet won't be particularly experienced with going on dates either.

While most will have experience dating, they probably don't have a lot on actually going on dates. According to statistics from a study provided in the novel The Rosie Project, both men and women will go on less than a dozen dates before finding "the one." 

Since they're around 40, it's likely they've had a break-up from a long-term relationship or marriage, and starting to see new people feels like unknown territory for them too. You both will probably feel like a fish out of water.

Here are a few things to help you on your date:

  • Suggest a fun or chill place: This puts the ball in their court if they would rather grab a drink somewhere or do something more fun (mini-golf, bowling, etc.)
  • Show genuine interest
  • Keep the first date on the shorter side: I've always aimed for under ninety minutes in case either of us find we're not interested in each other. No reason to waste time.
  • Use proper grooming: trim your nails, your beard, and use a spray or two of cologne.

The main idea, appearance-wise, is just to look like a man who is well put together.

flat design image of a couple on a date

 5. Start the Relationship With Someone You’re Seeing

You've made the final step where you've been seeing someone, and things are gradually moving to a relationship.

You're likely to be more emotionally mature than someone younger. Still, knowing how feelings can cloud your judgment is important. Try to control any negative emotions or reactions from happening.

It's okay if you experience those emotions; anyone can sometimes feel jealous or insecure. What's important is to not act on them.

Otherwise, there's not much sense in trying to break everything down. Being good at dating is a mixture of common sense and experience.

Why You Are Girlfriendless at 40

It's rarely a choice to be in this position, but it may have become one over time. Perhaps you tried dating without much luck or got frustrated by failures and decided to accept this as fate.

You may have became almost comfortable with it. It went to the back of your mind indefinitely, and you've moved on with your life.

What's Critical to Know:

After chatting with Aaron and several others, I discovered an interesting, consistent theme among them. They didn't just know how things led to this point, but on some level, they already knew how to fix it.

Perhaps it's similar to how anyone can lose weight with "proper diet and exercise." It's not exactly knowing how to fix the problem but rather the difficulty in the solution itself.

It's important to reflect and know how you got to this point.

Aaron spoke about how motivation towards improving his dating life (or lack thereof) didn't come out of the blue. He had already built up momentum in other areas of his life. Getting into a relationship was just next on his list.

I don't know what has held you back in the past, but it will undoubtedly come up again. Most of the guys spoke of a poor upbringing and experiencing mental struggles or issues at some point in their lives.

I can't speak of what to do or how to address it. At the very least, you should recognize the existence of these hurdles going forward, and try to address them in the best way you can.

Should You Tell Her That You've Never Had a Girlfriend?

You should tell her you've never seriously dated before, but waiting a bit is fine. 

If she's a legitimately cool and understanding person that's worth dating- she won't mind.

Everyone I talked to mentioned it to their new partner either right away or after a few weeks.

If you don't feel comfortable sharing that info, though, I wouldn't think it's a bad decision. At a minimum, you could say you haven't dated much over the years and just leave it at that.

However, it's reasonable to assume she'll have picked up on it anyway. So, you may want to be direct and not let it potentially weigh you down over time.

Getting to Sex at 40 if You’re a Virgin

About half the men I talked to about never having a girlfriend were virgins. Of those that weren't, they had all just been with one person.

If you're a virgin, I recommend being upfront and telling her. 

However, I wouldn't necessarily bring it up right away. Aaron was and told her after a month of seeing her, and they hooked up shortly after.

(they're still dating now too, over a year later).

While it could be a bit of a surprise to them, I doubt it will matter much overall.

I know this can be built up to being a bigger deal than getting a girlfriend itself. It's why some guys forego the traditional way and hire an escort/sex worker.

I'm not dismissing that option. I can understand wanting to immediately get something over with that's been hanging on your mind for decades.

However, if your motivation for doing so is based on the belief she'll dump you if she finds out, then I wouldn't recommend it.

This shouldn't be a deal-breaker to anyone who is worth your time.

flat design image of a couple in bed

Keep a Level Head and Avoid Discouragement When Dating

The good thing is, after all this time, you're probably a more independent person than most. That's an attractive quality, even though it may not always be easy.

The beginning of this process, especially learning the reigns with online dating apps/sites, will likely be the most challenging. Adding on any need to spend time in the gym or dieting could delay the results and feel demoralizing.

I won't say it will be a marathon rather than a sprint. You could schedule a date this week and be well on your way. Just know that it can take longer, and to always try to keep your expectations in check.

Go From Bachelor to Boyfriend at 40

Try not to dwell on the past and whatever got you here.

Be aware of any mental baggageYou can be optimistic about overcoming difficult hurdles, but don't let it derail you when you inevitably get knocked on your ass.

Value experience. I talked about using online dating and being willing to meet others below your level of attractiveness. While this is just how online dating mostly works due to the competition for men, there's still an added benefit for you- the experience.

Getting use to going out on dates and regularly interacting with women you like will be invaluable.

This way, if you meet someone you like in your regular day-to-day life, you'll be much better prepared.

Once you get some experience, check out my post 'how to get laid in your 30s' as it more deeply goes into how you can expand your opportunities. There's no real difference for 30s vs. 40s.

As for whether or not you should tell her you've never had a girlfriend, I would suggest doing so. There's no reason to be dishonest about it, and it's not the ideal way to start your relationship.

If you have any specific questions, message me on my contact pageIf you want to talk to Aaron specifically, mention it in the email, and I'll forward it to him. Good luck.

Related Questions:

What about meeting someone through my social or work circle?

If there's someone you like, you absolutely should go for it. The primary reason we recommend online dating as it's *basically* a surefire way to meet someone. You're otherwise limited by who or how many people you can meet.

What are some red flags to watch out for when dating?

When you lack experience, it may be difficult to always distinguish between what's normal and what's not. Some actual red flags: being dishonest, if they're easy to get angry, always negative, are dismissive of you, etc.

Try to give some slack overall, for instance, with the time between text responses and stuff like that. Otherwise, use your discretion. The reason she's still single might be different from yours.

What are some good conversation starters for first dates?

Most of this site is aimed towards young guys who are clueless about virtually all areas of dating and women (largely how I was at 20 years old). That same advice probably isn't as relevant to you. You likely know how to talk to people on a basic level and can just be yourself.

That said, it's still not exactly easy to talk with a stranger for over an hour straight. I recommend having some questions lined up for any awkward silences. It can be anything basic like about their family, job, hobbies, etc.

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