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How to get your Boyfriend to Propose to You

Amanda Valentine Dela Cruz

Are you at the stage of your life whereby you’re done with the peculiarness that comes along with trans dating? Do you want to tie the knot?  Most women find it very hard to open up this type of feeling to their boyfriends because of the fear of being rejected.

Added to that, a lot of men don’t find it appealing when a woman is very vocal about wanting to get married. Many guys run away when the talks of marriage are involved. If you want your boyfriend to propose to you without giving a hint of desperation, keep reading.

Things to Consider

Before you follow the tips that are listed in this guide, you must remember YOU. Marriage is not something that you should commit to unless you’re really ready. It’s not only your boyfriend’s feelings that you should consider.

Length of Relationship

As a transgender woman, this is a very important factor to look at. A lot of men in the world of trans dating are only experimenting. Some of them are also too young and are still unsure if they’re ready to enter a childless (biologically) marriage.

You don’t want to wake up one day seeing your man leave you for uncharted waters that he wants to discover. The length of the relationship will be quite telling if he’s really committed to you.

an hourglass

If he’s in his 20s or 30s and he hasn’t been with a cisgender woman and doesn’t have children of his own, the two of you should have been already dating for more than five years. Should he be in his late 30s and above or he’s already been married or have a child of his own, three years may suffice.

However, if both of you have exceeded past the seven-year-itch mark, he’s highly-likely in love with you. This is the perfect time to follow the tips that will be listed in the later parts of this guide.

Weight of Relationship

What kind of relationship do you have with him? Do you live together? Has he introduced you to his family and friends and vice versa? Do you barely meet because you’re in a long-distance relationship? Or are you simply a holiday girlfriend?

a nice couple

Assessing this may be hurtful most especially to the ones who don’t have a full-blown relationship with their partners. Marriage is a serious undertaking and unless the weight of your relationship is ample for him to consider exchanging vows with you, don’t even try.

His Dating History

Granted that you’ve checked the first two boxes, are you willing to marry a man who has a seedy dating history? Has he ever cheated on an ex-partner? Is he a womanizer? How many times has he been married? These are some of the most vital questions that you must have answers to before saying “I do”.

girl front of a laptop

Yes, the present and the future are both more important. But if you look at it in a more logical manner, you’ll know that most people have certain patterns when it comes to handling relationships.


Moving on to a more in-depth view of your readiness for marriage, you must assess yourself as an individual.

woman watching herself

Are you ready for Marriage?

Planning a wedding can be exciting but marriage is a whole different story. It requires a lot of hard work and dedication. Are you one hundred percent ready to share your life with someone? Will you be able to withstand the possibilities of financial, romantic, compatibility, etc. problems?

Added to that, committing to a husband also equates you, committing to his family and friends. Have you already established good relationships with them?

Is he the ONE?

Before getting married, ask yourself, is he really the one? Is he the man who you want to wake up next to for the rest of your life? Do you know all of his flaws and have you come to terms with them?

Furthermore, even if you think you’re already sure of his character, you shouldn’t be naïve to know that marriage reveals many undiscovered layers of a person.

Ways to MAKE him PROPOSE to You

Fast-forward to the part that you’re truly here for, the proposal. Please know that this section doesn’t guarantee that he’ll buy you a ring. However, the tips here are all beneficial in increasing the chances of him, proposing to you.

couple with sunrising

Subtle Hints

Subtle hints are quite effective when you want to get something out of someone. It’s not too aggressive and won’t make the other person feel like you’re desperate and demanding.

When you watch movies together and you see a house that resembles your dream home, you can mention how you’d like to live in a similar place someday with your future husband.

You can also excite him when you’re out shopping together. Pass by the kitchenwares and look at an oven. Cutely mention that you’d love to use it regularly to prepare a meal for your future husband.

Strategic Ultimatums

If he seems like a guy who responds more to limits and ignores subtle hints, it’s time for you to make strategic ultimatums. You can do this by mentioning certain ultimatums when the two of you cuddling.

“Honey, a really cute guy on the street asked my number. If you’re not going to marry me I’m gonna marry him”.

Doing so will give him a sense of urgency that he might lose you and he must take action.

You can also say,

“I’m really tired of explaining to my friends and family why we’re not married yet.”

This tactic will make him think that you’re already getting impatient and that he might lose you if he keeps disappointing you.

Straight to the POINT

If you’ve been dating him for more than five years and he has never even mentioned marriage to you, it’s time to get straight to the point. This may be a little riskier but at the very least, it will save you time and energy if he’s just indeed, stringing you along.

“I love you and you’re the man who I see myself with for the rest of my life. Do you feel the same way?”

After saying this, don’t make any follow-ups. If you do, you will appear very desperate to him. If he doesn’t give you a clear response, he’s probably just stringing you along.

Single and Looking?

Now, if you’ve only read this for fun and you’re still single in the world of trans dating, below’s a mini-guide on how to get things going for you.

Cyril and maki

Is your heart REALLY open?

Are you at the stage of your life whereby you’re ready to gamble again? Love comes with a lot of risks so unless you’re ready for the possibility of problems, heartbreaks, and disappointments, your heart isn’t truly open yet.

What type of Boyfriend to Look for

If you don’t want to keep making the same mistakes again, stop dating bad boys. Go for the gentlemen who handle relationships with respect, seriousness, and fidelity. Also, don’t say yes to the first guy. Spend more time getting to know a person before committing to a relationship.

Where to find a Boyfriend as a Trans Woman

My Transsexual Date is the leading trans dating site. The reason being is because it stands out from the rest of the competition. It’s built upon the foundation of the desire to create a safe and genuine place for trans-oriented relationships.

What are you waiting for? It’s time to get that ring!

Posted in Love and Relationship Tagged #

About the author

Amanda Valentine Dela Cruz
Just a random trans woman playing with makeup and skincare. Loves bacon and the operating table. I'm also the author of the dating guide book Dating Transgender Women for Gentlemen. Know more ->

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