How to Woo Her/Him 1, 5, 10 Years Into a Relationship

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Ask A Woman: Wooing at every stage…

You're hovering a bit there bucko.

If you’ve got a question that needs the female treatment, chances are you’re not the only one who wants to ask it. Beth is our source for the answers. From opinions on men’s style to decoding the sometimes mysterious ways of women, she’ll take on a different question every Thursday. She also might provide an answer without waiting to be asked. That happens from time to time too. Click here to get to know Beth, then get in touch with her by sending your question to: .


I get a TON of questions from readers about approaching a woman they’re interested in. This is the majority of my inbox. And I get it. Putting yourself out there, trying to meet potential dates, trying to turn old friendships into a new relationship–it’s hard. It’s scary, it’s painful. I’m happy to dispense advice (and if you’re one of these guys, feel free to shoot me an email). But I hate to ignore the dudes out there who have already met their person (man or woman) and are confident in the longevity of their relationship. If that describes you, listen up. YOU STILL HAVE TO DATE YOUR PERSON. Yes, even if you are married or living together or settled down with four children, you gotta woo your other half. What does wooing mean? It’s actions and words that let your loved one know you love them. Merely staying in a relationship is not enough–there are plenty of people who stay because it’s easier than leaving. You have to nurture your relationship on a regular basis. Here’s how.

You could climb up the trellis to a balcony…but there are easier ways to woo.

1 Year

You’ve been together a year. Hopefully you’re still sort of in the honeymoon period–you get a little thrill telling people that THIS woman is your girlfriend. (Subtext: how did you get so lucky?) Perhaps you’re still surprising her with flowers, or mystery dates. Good for you. I bet she appreciates it. You know what else she wants? Discussions about the future. At this point in a relationship, women typically feel secure that they are loved and appreciated in the here and now. What they aren’t as secure about is the future, i.e., where is this going? Pop culture makes fun of that question, but it’s a fair one, especially after you’ve both sunk a year into it (and the older you are, the more critical the future becomes). If you know you’re in it for the long haul, now is the time to start being open and honest about it. Initiate conversations with her about how you both see your lives in the coming years. This doesn’t mean you have to propose. It means you need to talk about whether you’re both interested in marriage or just long-term commitment, kids or no kids, whether your career path might require you to move and what would that mean for the two of you. If you really can’t bring yourself to tackle these topics yet, what about something less…permanent? Plan a vacation with her to South America for six months into the future. When your leases expire, talk about whether it’s the right time to move in together. These conversations and decisions are not what we typically think of as “wooing” behavior, but they function in the same way–you’re recommitting to your relationship and letting her know that she’s an important part of your life. (Side note: if any of these ideas make you feel ill when you think about them in relation to your current squeeze…maybe it’s time to reevaluate this relationship.)

5 Years

Although 5 years into a lifelong relationship is still very early, there tend to be bumps around this period. You obviously have a solid commitment, but the sparkle of a new relationship has long since dimmed. It is so easy to get caught up in work, friend and family obligations, and to never take the time to let your partner know you appreciate him.  It is just as easy to fix, that’s the good news. Here’s the formula: 1 kind word or action/day + 1 small gesture/week. Kind words/actions=”You look really nice today”; “I saved you the last bagel for breakfast tomorrow, I know it’s your favorite”; getting off the couch when he walks in the door from work to give him a kiss hello. Could this be easier? Try to do one of these per day. No need to plan it out, you can think of these kindnesses in the moment. Small gesture=bring home flowers/favorite snacks/a bottle of his favorite wine; mow the lawn or do all the laundry even if that chore is normally his responsibility; let him sleep in on Saturday while you get up to let the dog out or entertain the kids. These might require more planning (i.e.,stopping at the store on the way home from work), but still, it’s so simple to make these gestures. Try to do one of these per week. You’ll notice that none of these actions are huge overwrought displays of love and romance. If you’re into that, by all means, but it’s not required. You’re simply affirming, through kindness and small sacrifices, that you’re still crazy about your love.

10 Years

My suggestions for the 5-year mark hold true through all the rest of the years you’ll spend together. Try to make it a habit–the payoff in returned love and affection will be well worth it. But what about when you start reaching milestone years together? This time can be especially sweet, or especially stressful, depending on what life has thrown at you. Maybe you’re really proud of the life you’ve created together over these past 10 years, and you’re looking forward to the next 10. Or maybe you’re deep in child-rearing and you never get a moment to yourself, let alone a moment with your spouse. Perhaps both of your careers have taken off and you’ve dedicated this part of your life to making the most of your professional life while your personal life takes a bit of a backseat. Whatever your situation…this is the time for grand gestures. 10 years, 15 years, 20 years–it’s a big deal to reach these anniversaries. Act like it. This can be a flashy gift–diamond earrings or cuff links, designer handbag or briefcase. It can be a day of excess–spa treatments followed by dinner at her favorite restaurant followed by a play she’s been dying to see. It can be a vacation–a week on the beach in Hawaii, a trip to Rome, even cruising around the States in an RV to see all the places you’ve never been. Is money tight? No problem–what about a big-ass surprise anniversary party? Have it at your house (or borrow the abode of a friend or family member if your place is too small), ask friends and family to bring a dish or beverage to share, and shock the hell out of your partner when she walks in the door. You can even dig out all the photos from your years together and display them with funny captions on cork boards you’ve set up around the party area. Celebrating with good food and drink, close friends and family–what a wonderful way to honor the life you’ve created with your spouse.

Fellas, I’d love to hear your tips and tricks for showing your loved one that s/he still gets your blood moving. Do share.


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