Male-bashing articles are notoriously en vogue, admittedly for valid reasons. From the outset, let me clarify this won't be one of them. The difficulties faced in joining a man to a woman with previous (or more) relationship experience isn't just a “Muslim male” problem, but a social phenomenon with dimensions that need to be picked apart carefully and understood so that practical solutions can be proposed on a case-by-case basis.
A more intellectually honest approach that doesn't hop on the bandwagon of populist chest-thumping would force us to realize that firstly, this isn't a male problem exclusively – it is often the case when Muslim men bring home the idea of marrying a woman with previous relationship experience, it's mom and her gaggle of auntie ji's who shut down the idea for cultural reasons. The same women who remained in dysfunctional marriages because society would call them out (as well as lack of support options post-divorce) are now among those causing the biggest ruckus, so very clearly this is beyond being just a male / female phenomenon, but a cultural phenomenon with dimensions coming from both scriptural interpretation as well as local customs which even the non-Muslims of those areas share (e.g. India).
Putting aside the cultural side of the discussion, there's also the difficulty of Muslim male emotional insecurity. However, this isn't just a “Muslim” male problem. It's a male problem period for both Muslims AND non-Muslims. Do a Google search on emotional insecurity and you'll find scores of sexually active non-Muslim men struggling with the idea that their partner has more relationship experience than they do. It's not a “Muslim” problem, it's a human psychology problem that requires a mentor-like approach which encourages personal growth, not yet another polarizing male-bashing article.
I've read some noble attempts at getting brothers to marry our sisters with previous relationships with anecdotes like, “The man married the woman pretending he couldn't see how disfigured she was due to his nobility of character,” which is great until you realize you've just explicitly said these women truly ARE damaged goods and it's our duty to marry them for the good of society. Which sister wants her marriage to be some well-intentioned brother's community service pity project? I may be wrong, but I think ideally, our sisters want a husband who loves them for who they are, respects their humanity, and doesn't consider them as some type of cultural, physical, or emotional liability which they take on “for the good of the team”.
My belief is we have to re-orient our cultural misgivings to the standard used by the Prophet (SAW) and the Companions and remove the cultural stigmas surrounding previously married sisters, but as with all types of ignorance, this is a type of daw'ah and daw'ah has to be done with wisdom, not anger, sarcasm, and pseudo-intellectual arrogance. Likewise, we have to invite our brothers to overcome their emotional insecurities with mercy and practical mentoring strategies based on solutions provided in our scriptural literature as well as what is beneficial in secular sources. The intent of this article is to touch on the former (the cultural side) while spending more time on the latter (the emotional side).
Many years ago I considered marrying a divorced practicing Muslim sister and found within myself unexpected insecurities. By the blessings of Allāh, I was able to overcome them quickly and move on to seriously considering the sister for marriage. What I offer is my own thought process in overcoming issues such as these, and I would recommend using this as a complementary resource to whatever you find beneficial from Muslim or secular relationship counselors / experts.
1. Follow The Standard of the Messenger (SAW)
When any issue comes before me, the overarching principle that defines the direction I want to move is the attempt to find what it is that will be pleasing to Allāh (SWT), and furthermore, what standards did He (SWT) convey to us either in the Qur'an directly or in the life of the Messenger (SAW)?
Among the evidences cited towards marrying only previously unmarried women is the question of the Prophet (SAW) to one Companion about why he did not marry a virgin woman, and the oft-quoted hadeeth regarding those who are martyred receiving 72 hoor al-'ayn as reward.
What I've seen missing in that discussion is the life choices of the Prophet (SAW), and an understanding of those ahadeeth in light of his life since he is the paragon of Islamic practice – as Aisha (ra) mentioned, he was the walking Qur'an. His first wife, Khadijah bint Khuwalid, was a widow with children from a previous marriage, older than him (some narrations say 40, others say 28), a wealthy career woman, and the initiator of the marriage proposal.
This is extraordinary when you consider that The Prophet (SAW) at the time was 25, part of the most prestigious clan (Banu Hashim), a very handsome man, and well-respected by the community at large (he was known as al-āmīn, the truthful). He could have married any woman, and had there been any disgrace in marrying Khadijah, his uncle would have advised against it. To my knowledge it was never reported that people looked down on the Prophet (SAW) or made fun of him after Prophethood for this. If we look at his life in Madīnah, except for Aisha all his wives had been previously married and had exited their marriages either due to their spouse's passing or divorce. You may note that he also recommended marrying women who were fertile, yet he also married a woman who was likely not so (his second wife Sauda).
My takeaway from this is that while there may be some benefits in finding a partner without prior relationship experience, it's most certainly not the only factor to look at, and the weight it's sometimes given is disproportionate relative to more important variables (eg. Islamic practice, taqwa, character and manners, how attractive the person is, chemistry, chastity, life ambitions, child-rearing philosophy, worldliness, etc). I think there's a need for us to re-calibrate our standards and realize that if Allāh (SWT) doesn't evaluate people by these standards, perhaps we ought to re-align ourselves accordingly.
If there was nothing wrong for the Prophet (SAW) in taking previously married wives, I don't see how it should be a problem for the rest of us. He's our example to follow, and we should proudly take from it.
2. Remove Your Doubts and Hers with istikhārah Prayer
Deciding on a partner for marriage is a daunting undertaking and there are far too many variables to consider, most of them too far out in the distant future for any but Allāh (SWT) to see, so the best plan is to pray istikhārah and take guidance from Allāh (SWT) on the matter. The beautiful thing about istikhārah is if the marriage works out, then any lingering insecurities can be shut down with, “And this is what Allāh ordained for me, and this is what is best for me.” If things don't work out, that's good too, disaster averted. Share your decision with her, and let her know it was based on istikhārah prayer.
Beyond this, when there are insecurities that come to mind, you can turn to Allāh (SWT) to keep your heart firm on the guidance He's given you and make du‘ā’ for help in overcoming any mental roadblocks attempting to bar your way to happiness with this soulmate He (SWT) has chosen for you.
3. Take Control of the Inner Dialogue
Every single day, you will meet people who are bigger, faster, stronger, smarter, wittier, and more skilled than you. If you allow your mind to dwell on your weaknesses vs their strengths, then you will always see yourself as the lesser person. What can be worse in this situation is dwelling on what is unknown, wondering if you are being compared unfavorably against someone else.
As I mentioned earlier, it's important you move forward only after feeling confident in your istikhārah and making du‘ā’ to Allāh to help with your heart. Additionally, you should seek refuge with Allāh from Shaytaan and his whispering. Beyond this you have to also tie your camel, and part of this is taking time alone to reflect on your fears and try to understand where they're coming from.
Upon reflection, you may find that your mind is asking itself the wrong questions and answering with worst case scenarios, such as “What if I'm not as good as her previous husband?” and answering with “She will think me a lesser man.”
Part of solving this problem is taking control of that inner dialogue by asking yourself much better questions. If you've prayed istikhārah and feel confident you've made the right decision, you might instead ask yourself, “How much barakah and love will Allāh (SWT) place between us because we are doing this to please Him?” and you may start to imagine a scenario in your mind where your wife is wildly in love with you and you with her. The more often you do this, you'll find your heart at ease, and the other question will become like a fly buzzing around your head, easily swatted away with du‘ā’ to Allāh (SWT) and the strong, positive emotions in your heart.
The ultimate confidence is knowing that Allāh (SWT) supports you, and when you know that, you cannot help but imagine the best is yet to come, both in this life and the next, no matter the difficulties you encounter along the way.
In the end, the marriage with the divorced sister didn't happen for me (she ended it) and we parted amicably for the sake of Allāh (ok, so the first few days I was really disappointed, but it passed :)) and although I didn't have to revisit the issue, I was thankful for the experience because I grew tremendously as a person and I gained an appreciation for the difficulty both women with previous relationship experience face in finding husbands and the difficulty some men may face in overcoming their own fears and insecurities.
If anyone were to ask me about a situation similar to mine, I'd tell them to not turn away the sister just because of their insecurities or cultural stigmas. If you find you have insecurities as I did, then take it as an opportunity for growth and work on overcoming them while seeking help from Allāh (SWT). It may be that her previous relationship and the lessons from it is the means Allāh (SWT) has chosen for both uniting you with her as well as teaching her, based on experiences from her previous relationship, to appreciate the good that you possess.