Meeting Your First Love After 40 Years (13 Tips For Handling A Reconnection With Your First Love)

No matter how many years pass, you can’t say you forgot or just stopped loving your first love. The romance, dating process, and shared experiences stay with you for life. Over the years, you’ll discover yourself thinking or talking about him. 

You might even imagine what his life is like now, who he is married to, the faces of his children, and many other things you shouldn’t be thinking about regarding your first boyfriend from years ago. Then, like a page torn straight from a storybook, this man from your past waltz right back into your life, leaving you more than a bit confused. 

Both of you were probably high school sweethearts for crying out loud. You’ll start wondering why now, why me? If you’re in a relationship, your confusion increases because, how do you reconcile those buried feelings with the realization of how much has changed since he got away? 

13 Tips For Handling A Reconnection With Your First Love 

If you’re single and searching for the right man, you’ll probably take this as a sign to resume dating. You might even react out of protective instincts because you don’t want this lost love to think you’ve been waiting nervously and pining after him for those long years. 

However, dating after 40+ isn’t the most fun thing to do because even young adults sometimes find the process tedious and frustrating. So, are you in this situation where you recently met your first love whose love you want to reclaim? 

Does he seem to want the same and is talking about marriage already? Well, slow him down. Read these tips before pledging your commitment to your lost love.

1. Take a deep breath and appreciate the second chance

So, you lost touch with your first love from years ago, but now he is back and finding his way into your heart again. You probably met him at your school reunion many years after both of you parted ways. You’re either giddy at the sight of him or furious and hurt because of how things ended. 

The pain of failed early love never goes away completely because you gave your all and felt deeply. You’re overwhelmed because behind the anger, there is still a smidgen of leftover love from the past.

Before making any choice, take a deep breath and don’t give him any reply yet. Dating the opposite sex whom you don’t know anymore should be a slow process, so don’t rush yourself to take any step.

2. Don’t make hasty decisions

When you meet an old flame again, the wisest thing isn’t jumping back into bed or a relationship with him. Such relationships require wisdom and stealth because they can easily leave you more wrecked than the other time.

If dating him years ago didn’t do much good for you, doing so now might not be the best thing to do either. You don’t know why he is seeking you out, so don’t rush anything. 

It might take a while to know his true feelings for you, but you need the waiting time. With patience, observation, and help from a good friend or a relationship expert, you’ll discover what he wants from you. 

3. Get to know him again

Although this person used to be a big part of you so many years ago, now he isn’t anything but a distant memory you’re trying to resurrect. So, you should start afresh with him. Try to know him as you would a stranger. 

Ask him questions like has he ever been married? How many times has he been married? Why did he get out of those other women’s lives? Of course, don’t be unreasonably intrusive at the beginning of your reconnection. Ask the questions with care and only after both of you are a bit comfortable with each other.

If you’re satisfied with his responses, you can give him another chance. You might think you’re too old to play the dating game, but the goal is to stay forever young at heart right? However, don’t play games or dirty tricks because you don’t want to waste the precious time you have. Dating is a game, it doesn’t have to be a dirty one.

4. Start as friends

Trying to start a relationship immediately with someone you don’t know too well is a risky move, even if you once dated him. Instead, propose a friendship to him if he suggested that he wanted to start dating you. 

If he’s been married before, does he have children? You might want to consider the implications of this as his children and their mother(s) will always be a part of his life.

You don’t need to deceive yourself that all you want from him is to be just friends, but taking things slow is best for knowing what his intentions towards you are. After you get his reason for pursuing you again, you can make a decision. 

5. Acknowledge that you’re different people now

acknowledge that you're different people now

You need to remember that you’re not in the same situation as in the past. Both of you have grown in age and experience. You’ve developed interests different from the ones you knew years ago. His beliefs might have changed and no longer align with yours.

Your taste in men might have even changed, so he lost the right to just slide right back into your personal space. 

If he was married before and you’ve never been, his attitude would be slightly or greatly different because he has cohabited with a woman for years in ways you can’t relate to. As such, you need to get to know him properly before starting anything again. 

6. Take off your rose-tinted glasses

Dating your first love the second time around can be looking for trouble because you’ve been apart for years. He might be lying about not being married. He could have a marriage problem and is looking for a short-term escape. 

He might even be down on his luck and looking for ways to scam ‘a well-to-do lonely mature woman’. He could also be happily married for all you know. There is no shortage of possible scenarios for him seeking you out. You just have to be on your guard

If you have ties to mutual friends or his family, confirm the details he provides you with before allowing him back into your heart or bed.

7. Why did he get away the first time?

You can’t just forget why it didn’t work out the first time, or why you’re not the one he married all those years ago. If he walked away from you, there is a need to revisit why he did so. Were you the guilty party who made things go bad? Was he the one who left without giving both of you another chance? Did either of you cheat in the romance?

When things get tough in young relationships, both parties can be overwhelmed. You don’t want to face what you did those years ago. As such, you need to talk about it no matter how uncomfortable the subject is.

8. Try not to make the same mistakes as before

If you’ve decided that you want to give both of you another chance at love, you should confront the mistakes you made before. What either of you did wrong before might matter, but it shouldn’t be the only factor determining whether you can start a new relationship or not.

Relationships are bound to have challenges regardless of how old the partners are. However, you’re both mature and wise enough to avoid the mistakes that kept you apart all those years. 

You can now navigate through the muddled feelings and draw on the lessons you’ve picked up from your experiences with other people you’ve dated or married. Honestly, if you get it right this time around, your reunion would be the best thing that ever happened to both of you.

9. Is he truly the one for you this time around? 

If you’ve mostly found lovers who are selfish and dismissive, it will be hard to trust even this person you once knew. All your life, you’ve been waiting for the right one but he never showed up. During the first love, you thought you’d never have to search anymore, but that didn’t work out. So, why trust that things with this same man will check out? 

Consider his life choices and how they can affect you positively or otherwise. Is he doing things that will give you peace of mind even as both of you grow older together? Will he stand by you even when things get a bit rough? By the time you get answers to some of these questions, you’ll know what to do next. 

10. Don’t let desperation cloud your judgment 

don't let desperation cloud your judgment

You’re in your late 50s or early 60s, not aged and senile, so don’t let your waiting period become a despairing experience. You might have waited patiently for the right person, there’s no point rushing into a mistake now, not even with your first love. 

Some existing marriages will fail, some will survive. You don’t know which category you will fall into until you start making conscious efforts to make it work. As such, don’t be in a haste to make any long-term commitments to him because you don’t want to grow old alone.

You might have your own insecurities, but so does he. The difference is that most men know how to conceal their insecurities more. As such, enjoy your time with him without putting unnecessary pressure on either of you.

11. Meet in neutral places. 

Remember, old feelings (or habits) die hard. When you rekindle your romance with your first love, don’t get all cozy immediately. Let your first meeting with him happen in public so you’re not tempted to test the physical compatibility so soon.

With time and conviction, you can explore that area.

12. Don’t introduce him to your family just yet

Even if you’re dead sure that he is your true love then, now, and always, don’t be in a hurry to introduce or reintroduce him to your family. He might even be old friends with your siblings, but he is more or less a stranger now.

Give it time before you start integrating him into the intimate parts of your life. 

13. Go all in once you’re sure he’s still a solid man

Don’t take all the things he is saying to you at face value. Do your findings, but don’t spit in the face of a second chance when he proves to be a solid man. If you’re going to be just good friends, then he might be the one companion who will be there for you in your prime years.

Don’t waste time on regrets or old pain when you could be having the time of your life with the first person you knew for sure loved you.


Do first loves get back together later in life?

Some first loves get back together, especially if their paths run in the same direction. Social media has made it easy for some old flames to keep track of and reconnect with each other. 

Does a man ever forget his first love?

If she was remarkable, even a man doesn’t forget his first love. He might not dwell on her as his basic sexual needs make it easier for men to move on, but he will remember her once in a while. 

What percentage of first loves get back together?

Generally, about 75% of first loves reunite and stay together for a long time or lifetime. However, there are no guarantees as some of that percentage can still run into problems and part ways down the line. 

Is it normal to think about your first love years later?

It is normal to get flashbacks of your first love many years after you saw him last. Your trigger could be something unexpected.

Is marrying your first love bad?

Marrying your first love isn’t bad at all, as long as you’re sure he is the person you want to spend your life with. 

In Conclusion

Rekindled romances are like putting on old well-worn shoes – they fit so comfortably. They are like an old friend who shows up at the right time when you need them, but you still need to be careful so you don’t get hurt. Reconnecting with your first love is a sweet but tricky situation, so go in with your eyes wide open this time.

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