How to Prepare for Your First Date After Divorce

Here’s how to prepare for that all-important first date after divorce: from 7 tips for successful flirting to 16 first-date Dos and Dont’s.

first date after divorce couple photographing their dinner

Are you past the “walking wounded” stage of divorce recovery? Have those intense feelings of anger, hatred, or grief died down to background noise? Have you stopped talking about how awful your ex-spouse is to whoever is unlucky enough to sit beside you on a bus/train/plane? And have you spent some time discovering who you are after divorce – and what your must-haves and deal-breakers would be in your next relationship? If so, it might be time to test the waters in the dating pool. Here’s how to prepare for that all-important first date after divorce: from successful flirting to first date Dos and Dont’s.

The First Step is to Find Someone Worth Dating

Now that you’re emotionally ready to meet your soulmate, you have to find him/her. Here’s a hint: he/she probably isn’t sitting on your sofa waiting to watch “Westworld” with you. So you’re going to have to leave your comfort zone and put yourself out there. This doesn’t mean you have to start hanging out at singles bars or attending political rallies (unless you like these sorts of activities). Slowly begin to do things you like that will also get you out of the house and meeting new people. Start taking art, dance, cooking, stand-up comedy, or car-repair lessons; take up tennis, golf, rollerblading, or skiing; go to parties – even if you don’t feel like it; volunteer for an animal rescue organization, traveler’s aid, or your local hospital. You’ll be meeting other people who share your interests, which gives you an easy opener when striking up a conversation.

And when that special someone shows up in your life, try to flirt instead of running screaming for the hills.

How to Flirt on Your First Date After Divorce

Whole books have been written on this topic. My best advice is to lead with your strong points, even during an initial exchange. For instance, if you aren’t funny (you know who you are!), don’t try to tell jokes. Still, try to keep things light at first: small talk actually puts people at their ease and can open the door to deeper conversations.

Take a cue from your surroundings: if you’re standing in a long checkout line, try: “I always seem to choose the line where someone is using 185 coupons; we’re going to be here for a while!” or “Doesn’t the cashier look like Jennifer Lawrence?” or even “Gosh, it’s hot/cold out today!” After a couple of non-threatening exchanges about nothing important, you can try to find some common ground to create a bond between you and the dreamboat. For instance, you could say, “I’m a bit stiff today: I went rollerblading yesterday for the first time. Do you rollerblade?” If the answer is yes, you can talk about rollerblading for a while: where you go, the equipment you use, what you like about it. If they say no, but is still looking at you in a friendly way, you could try offering a genuine compliment: “That suit/dress/color looks great on you.” They may respond by telling you where they got it, then you can ask a question or make a (positive) comment about the store.

If you are genuinely funny (ask your friends to be honest with you about this), you could opt for an amusing or offbeat opening line.

Body language is an important part of flirting. This includes smiling (but don’t try to mimic the Cheshire Cat from Alice in Wonderland) and standing just a little bit closer than you normally would with a stranger. Warning: there’s a fine line between showing interest and pushing someone into a flight-or-fight response: don’t stand nose-to-nose, and don’t back the person into a wall or corner. This is just plain creepy and will guarantee that your victim will never want to set eyes on you again.

Try mirroring the person’s body language: if she leans forward, you lean forward; if he crosses his left leg, you cross your right leg. Again, don’t overdo this: your aim is not to mimic the person, but to put him/her at ease.

Here are a few more tips to set you on the path to successful flirting:

  1. Always try to look your best before engaging in flirting. If your hair is a disaster, you haven’t brushed your teeth, or your mascara has run half-way down your face, you’re not going to exude the cool self-confidence a successful flirt requires.
  2. Offer a genuine compliment. This could be physical – “You have such beautiful eyes” – or not – “You laugh easily. That’s a trait I really admire.”
  3. If you’re good at it, tell jokes (make sure they’re neither dirty nor disparaging, though).
  4. Never brag – not even if you’ve just won the Nobel Prize or the Oscar for Best Picture. Nothing demonstrates insecurity better than bragging – and it’s extremely irritating to be on the receiving end of a bragger in full spate.
  5. Be fearless. The worst that can happen if you approach that gorgeous creature is that he/she will reject you. Contrary to what you may feel at the time, this will not kill you. The best is that you may succeed in captivating the most interesting person in the room. Isn’t that worth a bit of bruised ego?
  6. Be interesting. To charm an interesting person, you need to be interesting. So disconnect the TV and get out there. Push your physical and emotional boundaries: whether that means trying skydiving or yoga. Also, reading some great books will help to wake up those sleepy brain cells.
  7. Get help. Ask a friend who’s a great flirt to give you tips and coaching on everything from body language to ice-breakers to how to tell a joke.

The First Date After Divorce

Okay: so one of you has gotten up the nerve to ask the other on a date. Now what?

Again, start with small talk. I don’t care how much you hate it: a first date is always somewhat nerve-racking, and small talk puts people at ease, giving them a chance to regain their balance. Usually, small talk lasts no longer than about five minutes; some people require more time, and some require less in order to relax.

Your next challenge is to find a topic of mutual interest to discuss. This may take a couple of attempts, so don’t be discouraged if your first conversational arrow misses the mark. Try hobbies, sports (spectator and participatory), each other, movies, books, and music. If you are genuinely funny (ask your friends to be honest with you about this), you could opt for an amusing or offbeat question. Avoid politics, religion, and your ex-spouse. Of course, you’re not going to lie about the fact that you’re separated or divorced – just don’t give them a two-hour monologue about the breakdown of your relationship.

This is enough information for a first date: “I’ve been divorced for about two years now. It was a friendly divorce, and I wish my ex all the best.” This lets your date know that you’re over your last relationship and that they won’t find themselves in the middle of a psychodrama involving you and your ex if they get into a relationship with you. Warning: if your date starts spewing hate and vitriol when discussing his/her ex, run for the hills! Do not get involved with this person – unless you’re interested in years of misery and possibly even danger if these two are still locked in a toxic, hate-filled post-divorce relationship.

So after you’ve bonded a little over your shared fondness for Drake, it’s time to start offering and asking for a little personal information. Since a woman will normally have a few safety concerns about spending time with a man she doesn’t really know, a man should let her know he’s “safe” by offering some information about where he works, goes to church, works out, likes to go with his friends for a beer after work, etc. This demonstrates that you a) have a life of your own, and b) are a fairly normal guy with no big secrets (like you’re actually married with three kids or that you’re currently out on parole).

Don’t interrupt (unless to warn of imminent physical danger: “Look out for that runaway piano!”), lecture, or interrogate your date. Ask questions designed to elicit more than one-word answers, but don’t make your date feel as though you’re interviewing him/her for the position of “next spouse.”

Paying a genuine compliment is always a good idea. “You have a lovely smile,” “I love dancing with you,” or “You look great in that dress” are all good examples. Being overtly sexual is not a good idea on the first date, so refrain from commenting on breasts, butts, etc. even if you find them exceptionally nice. By the way, if someone compliments you, the correct response is: “Thank you! It’s so kind of you to say/notice.” Don’t deflect it – “I hate my teeth,” “What – this old rag?” or “I have two left feet” are examples of ways not to respond to a compliment. Even if receiving praise makes you feel shy or awkward, deflecting it will make your date feel stupid, hurt, or annoyed.

3 Questions to Ask on Your First Date After Divorce

The four Harvard mathematicians who built the OKCupid dating website suggest asking the following three questions on your first date to determine whether you are truly compatible with someone:

  1. Do you like scary movies?
  2. Have you ever traveled around another country alone?
  3. Would you like to ditch it all and go live on a sailboat?

They claim that if someone answers all three questions the same way you do, you’re a perfect match for each other! If you decide to try online dating, these math whizzes have some advice when it comes to posting your profile photo: “The best pose for men is ‘mysterious and sexy,’ looking off camera and not smiling, whereas women who hold the camera above their head and look coy and flirty receive more hits.”

16 First Date Dos and Don’ts
  1. Do show up on time; tardiness shows a disregard for your date.
  2. Do observe rules of proper hygiene: dirty hair, unbrushed teeth, and lingering B.O. are turnoffs and very disrespectful.
  3. Do make your date laugh (hopefully with you rather than at you). Tasteful jokes and comments only, please: no racist, sexist, or dirty jokes.
  4. Do pay him/her genuine compliments.
  5. Do listen at least as much as you talk; make an effort without dominating the conversation.
  6. Do make lots of eye contact.
  7. Do mirror your date’s body language.
  8. Don’t talk about how you’re doing on other dating websites.
  9. Don’t answer your phone or send text messages (aside from genuine emergency).
  10. Don’t dress inappropriately. If you’re not sure, ask – it’s less embarrassing than showing up wearing jeans when your date is formally attired.
  11. Don’t ramble on about your ex’s failings.
  12. Don’t interrogate your date. The object is to have fun while getting to know each other – not to interview for the position of “my next spouse.”
  13. Don’t brag or lecture.
  14. Don’t fight about who picks up the check.
  15. Don’t lead with your tongue if you’re trying to initiate a good-night kiss.
  16. Don’t sleep with someone on your first date.

The End of the Evening

It seems ridiculous, but the issue of who picks up the check can turn a great first date into a minor nightmare. We all come to this with different assumptions: some people feel the person who asked for the date should pay; some people feel the man should always pay; some people feel it should be dutch-treat. Unfortunately, if your assumptions are different from your date’s, it can generate a huge misunderstanding about your cheapness/chauvinism/outdated values/ego – whatever you make the act of paying mean.

The best way to avoid this kind of incident is to establish right off the bat what your expectations are. When making the date, say: “I’d love to treat you to dinner. How about Luigi’s on Friday night?” If this advice comes too late for you, initiate a short discussion about it during the date. You can make it impersonal by talking about a “friend’s” experience: “My friend Sara had a strange experience last week. She was out on a date, and when she offered to pay half, her date became very angry with her: he accused her of thinking he was cheap, or unable to pay. She was just trying to be polite. It’s so confusing these days… Do you think she was wrong to offer?” You’ll bond a little on the issue of how confusing modern etiquette is, and you’ll find out what your date thinks about who should pay.

If your date expresses a strong opinion, try to respect it. If he wants to pay, but she feels a little uncomfortable about it (maybe she makes more money than him, or maybe her ex-spouse was so cheap she simply isn’t used to being treated), she could say: “Thank you – that’s very kind. I’ll treat you the next time.” Do not fight with your date, or try to snatch the check out of his/her hands. Be gracious, and make sure you’re clear on what the deal is for the next date before you go out.

The next thorny issue: to kiss or not to kiss? Well, that depends a bit on how the date has gone. If you’re not interested in repeating the experience, say, “Thank you for the evening,” and shake hands. Note: do not say, “I’ll call you” if you have no intention of doing so. Just thank the person, and walk away. If it has gone really well, look for clues that your date wants to kiss you. These include:

  • Lingering outside your car or front door.
  • Touching your face.
  • Taking both your hands and gazing into your eyes.
  • Leaning towards you and gazing deeply into your eyes.
  • Saying “I’d like to kiss you – is that OK?”

If your date exhibits any of these behaviors, you can offer a kiss on the cheek, or a light kiss on the lips. No tongues, and no hip-grinding! If your date doesn’t pull away after the kiss, and you’re equally smitten, you can offer another, slightly deeper kiss.

Regarding sex on the first date: unless you’re looking for a one-night stand, you probably shouldn’t do it. Aside from any other concerns, there are diseases you can catch that will kill you – and despite what some people still think, you can’t tell whether or not someone is safe by looking at them. Money and social standing is not an indicator that they’re disease-free, either. When you sleep with someone, you’re also sleeping with all his/her previous sexual partners – that makes a lot of people in bed with you! You cannot sleep with someone until you’ve had a frank talk with him/her about sex. If you’re too embarrassed to discuss safe sex, you’re not ready to have it.

Diana Shepherd is happily divorced and an online-dating veteran. She is also the Co-Founder of Divorce Magazine.

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