Dear Wendy
Dear Wendy

“How Can I Make Myself Date Online?”

I’m 32 and have been divorced a year. I’ve had a couple of boyfriends since my divorce, one of whom I really liked. That relationship ended at the end of the summer and I took a few months to get it together. Since I started dating again, I’ve had terrible dates. Like, sitcom bad. So, after much cajoling from my best friend and my sister I signed up for Match.com a few days ago.

The problem is that I panic when I log in to the site. I start breathing heavy and my stomach has knots in it for hours. Part of the problem is that I live in a small town so some of the guys on there are guys I know, one of whom is pals with my summer boyfriend. In fact, one of the pics I put on the site is from a camping trip that he was on with me and the old boyfriend. How do I make myself do this?????

I would like to have a boyfriend or at least a few dates with someone that were good enough so that by date three or four I was making a conscious decision as to whether or not I should shave my legs. Please help me figure out how to psych myself up. I wish adult life were like college life – plenty of boys and plenty of dates. Or, I wish I could just calm down and maybe respond to a message. β€” Fish in the Sea

You know, a lot of people would argue your point that college has plenty of boys and plenty of dates. You’re only 32 β€” surely you remember some of the pain in dating 19-year-old boys. Surely you remember being 20 years old and wondering if the guy stringing you along with a coffee date here and a booty call there was interested in anything more than just fooling around with you. But instead you choose to remember your time in college as a banner time for dating. Why? Probably because even in the midst of all that insecurity and disappointment, you were having fun. So why not apply that same attitude to your current dating situation?

You’re single! You’re young! Don’t put so much pressure on yourself to have the best. dates. ever. You don’t have to decide by the third or fourth date if you’re going to shave your legs. Shave them on the first date and feel good about yourself! Who cares if there’s some guy on Match who knows a guy you dated for a few months. Big whoop. Lots of people log onto dating sites to find their exes. Be glad you’re simply running into a friend of an ex. Who cares? You think the friend of your ex is sitting in front of his computer, his stomach in knots, breathing into a paper bag because he saw your profile and he’d like to ask you out but he’s not sure he should since you briefly dated a friend of his? Come on.

You know what you need to do? Date like a guy. Date to have fun and find someone you might like to fool around with. After a divorce, followed by two short relationships that messed you up enough that you needed a time-out for several months, you deserve to just have fun for a bit. If you see guys online whom you know, look at that as an immediate ice-breaker. Send a little note saying, “What’s a guy like you doing in a place like this?” Neither of you is doing anything to be ashamed of, so quit thinking you are. If you ran into someone you know at a party would you have a panic attack then? No (at least, I hope not). You’d say hi and be happy to have someone to talk to. Apply that same logic online. It’s really not that different.

And look, if the thought of dating has you so freaked out, maybe you aren’t ready yet. There’s no shame in that. I don’t know the details of your marriage or divorce or the relationships that followed it, but you do say you had to take a few months to “get it together.” Maybe you jumped back into dating too soon following your divorce. Maybe your confidence was shaken when your marriage ended and it took another beating in the preceding relationships. Are you sure you’ve healed from all that? It’s okay if you haven’t. Be honest with yourself, though, and give yourself permission to sit things out a bit longer until the wounds have healed. Just because your sister and best friend are pushing you to get back out there doesn’t mean they know best. Listen to your gut and do what feels right to you.

*If you have a relationship/dating question I can help answer, send me your letters at [email protected] and be sure to follow me on Twitter.

21 comments… add one
  • avatar

    silver_dragon_girl January 10, 2012, 9:00 am

    Amen to Wendy’s advice. And LW, the way you feel online dating is the way I feel talking to potential dates I’ve met in real life. Which is why I always dated online πŸ˜› So keep that in mind- everybody has certain methods they like to use, and things that are outside their comfort zone a little bit. So relax and have fun. Remember, everyone you’re talking to on that online dating site is *also* on an online dating site…so if you have any hesitations based on the old, tired, “this is pathetic and desperate” stigma, keep telling yourself that. The internet is just another avenue to meet people.

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  • avatar

    SweetPea January 10, 2012, 9:14 am

    Wendy is absolutely correct with this advice.

    I could be mistaken, but I think match.com may have a function where you can put your membership on hold (and not lose out on whatever money you’ve spent). If you decide you are not ready to date… then use this! And come back to it when you are.

    But, if you really think you want to give this a go- then do like Wendy says and have fun! I used to look at the bad dates as good stories! There was a time I considered writing a dating memoir because some of my dating mishaps were just too funny not to share (the guy who stopped in the middle of kissing me to creepily say “Somebody likes kiiiissssssing me!”… cracked my friends up anyway!). If you have a bad date, so what? But, I guarantee you some of them will be great dates. You might find your soul mate and you might meet some friends and might just meet some nice people to chat with while eating at a cool restaurant you’ve never been to.

    Be sure to take baby steps if you need to. You can exchange a few messages with someone and decide you don’t want to meet them after all. Don’t feel the need to jump in head first.

    Good luck πŸ™‚

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    • avatar

      silver_dragon_girl January 10, 2012, 9:20 am

      You know, when I first started online dating a couple years ago, I did the same thing. I would go out with just about anybody who asked and seemed even remotely date-able (because I was bored and lonely in a new city), and then have tons of good “bad date” stories to tell. It was kind of fun. Just be careful you’re not leading anybody on about being more interested in them than you really are.

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      • avatar

        SweetPea January 10, 2012, 9:23 am

        Well, if a date were particularly bad, I made sure not to go on multiple dates with them. And would let them know as kindly as possible that I wasn’t interested. Sometimes the chemistry is there in internet world, but not in the real world. And… that’s okay. I was never mean-spirited about it.

        I just have to make fun of life sometimes over a few beers with friends!

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      • avatar

        silver_dragon_girl January 10, 2012, 9:49 am

        Oh, yeah, totally! Sorry, I didn’t mean to imply that you might be leading people on, it was meant for the LW, if she should decide to try that method for a bit πŸ™‚

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      • avatar

        blueskies January 10, 2012, 12:59 pm

        Hahaha…you guys sound a lot like me. That’s exactly how I try to look at some of the bad dates: good stories. πŸ™‚ You need to see the humour in it.

        I also try and see online dating as a venue to meet people that I’d never get the chance to in real life. Really, being online gives you so much control over who you WANT to date, and no pressure if things don’t work out. (Unlike that time I was set up with a friends brother– disaster).

        So to the LW….take a deep breath (heck, take a break if you want)….and when you’re ready to start dating again, know that everyone already knows you’re single. No one is going to be shocked to find you on there. And if they are….well, they are creepy internet trolls who really need to get a life. πŸ™‚

        Good luck dating. As Wendy said…try to have fun with it.

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  • Budj

    Budj January 10, 2012, 9:16 am

    I would ask the LW if she really thinks that online dating is for her. Some people don’t like the “organized but still subjectively random” match up system you are entered in and prefer to know someone prior to dating…i.e. meet at a social setting in person (or meeting through mutual friends) + hitting it off = date success odds drastically increase. If this is your mentality, LW, then get off of online dating.

    As an alternative – if you don’t think random match-ups are your gig then try to find a co-ed social hobby or go to in-person dating events since you have a much better / more comforting idea of a person without a computer filter between you. Being able to read body language and see how someone carries themselves is such a quick way to accept or deny a potential suitor and hone in on someone that won’t give you a sit-com worthy date.

    Additionally, small town online dating is exactly what you would expect it to be…not many options unless you want to drive to your nearest city. My small town isn’t even that small and I couldn’t find match ups within 2 hours of me…granted I never tried Match…

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    • avatar

      GatorGirl January 10, 2012, 11:56 am

      I’ve heard of a couple “single events” companies that plan free (and for-cost) events for singles to meet each other. Also maybe try speed dating? There are lots of ways to meet people other than just match.com.

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    • Leroy

      Leroy January 10, 2012, 2:27 pm

      I think that the idea to look for events and meet-ups is a good one, less pressure and a better opportunity to present yourself and feel people out. And as Wendy’s recognized, the LW seems a little beside herself right now. It might be a good idea to put aside the search for a boyfriend and just enjoy meeting new people.

      Also it’s not really necessary to use online dating in a small town/city. If you put yourself out there, you’re going to meet the same people you’d have met online anyway.

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  • avatar

    utopiaballroom January 10, 2012, 10:13 am

    I think something that really bears discussing is the timeline here. LW has only been divorced for a year. Depending on how long it took between deciding to get divorced and the paperwork getting finalized AND depending on how long the marriage lasted, LW may still very well be grieving the marriage.

    A similar thing happened to me when I got divorced. I went on a few dates with random people, then had a boyfriend for a while, but it just seemed kinda…weird and sad? At one point, I signed up for a dating site. It was absolutely terrifying, even though I felt like I should’ve been doing a lost more to…I don’t know…make the most out of being single again, I guess?

    ANYWAY, the moral of the story is that I just wasn’t really ready to dive headfirst into the dating pool again. For many people, a divorce is processed like a death, and LW might need to relax and give herself a little more time to grieve.

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    • avatar

      Kristen January 10, 2012, 11:45 am

      I agree with you. A lot has happened with the LW in the course of a single year… divorce, a couple of ended relationships… I think she’d feel a lot less anxious about online dating (and dating in general) if she took several months to just focus on herself. It’s been a long time since she’s been single, and she needs time to reassess her life and interests before jumping into another relationship.

      LW, I think if you decide to continue with online dating, you should look at it as a casual way to meet people. Don’t put a ton of pressure on yourself and wonder if every date is marriage material. Relax for awhile and rediscover who you are as just YOU. Once you do, you’ll have a better understanding of who is right for you and who isn’t… and you’ll have a wholly intact heart to offer that person.

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  • avatar

    Elle January 10, 2012, 12:59 pm

    Wow, LW, your timeline sounds just like mine. By coincidence, I had the first date on the day that the divorce decision was granted by the court – I had separated from my ex a year before that. But on that date, and on the many subsequent dates I had, I always managed to find something in each guy that reminded me of my ex. A couple of years later, I realized that my walls were up to the sky, and I didn’t give anyone the chance to get closer, for fear I would get hurt again. Then I let my walls down for someone who didn’t deserve it. So I got hurt anyway, but I moved on.

    My point here is – are you sure you’re ready to date? If opening a website gives you an anxiety attack, maybe you shouldn’t be dating right now? You wrote that your sister and friend push you to date – if it’s not something you’d be doing on your own, you’d be a lot better off not doing it.

    As someone who’s been doing this online dating thing for a couple of years, I don’t understand where you’re coming from (sorry). It’s just a website. Just because you read someone’s profile doesn’t mean you have to meet them. Just because you receive an email from someone doesn’t mean you have to reply if you don’t like their profile (Just FYI, I don’t reply to messages like “hey butiful how r u wanna chat”).

    I’ve been on a few dating websites – all of them had the option to block someone. If you no longer want to see a guy around the website, click “block”, and he poofs.

    One particular website (a free one, and I’m not sure Wendy would like me to advertise it here) gives you the option to hide your profile, and you can only email guys you’re actually interested in. Only after you contact them they can see your profile, and can decide to reply if they want. Is this what gives you the anxiety – that other people can see your profile and it’s out of your control? With this option, you have COMPLETE CONTROL over who gets to see your profile and who contacts you. You should be prepared though to have a very low response rate.

    You mention you live in a small town – I feel for you. I lived in a small town last year, and I didn’t have any luck. Most of my dates were from towns 30-40 miles away, at least.

    General observation about dating websites – you’re going to see most of the same people on all websites. I did notice it a lot, especially since they would copy/paste their profile, and use the same pictures. (My stalker was on all of them, and the first message on every website was from him. I loved the ‘block’ option!). My personal experience – I wasted money on Match.com. I only got one date, and I think he used me to train for his future dates, because I never heard from him again, even though I thought we had a good date. On the free websites though, you have to put in a bit more work – you have to read a lot of profiles to find an interesting guy, and even then, he might not reply to your message.

    Best of luck to you! (Maybe you could ask for Wendy’s help to improve your profile? Just a thought)

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    • Will.i.am

      Will.i.am January 10, 2012, 5:02 pm

      I’ve thought about trying Match.com, since I haven’t had romantic luck with plentyoffish.com.

      The hardest obstacle for me is being a black male who is highly interested in white women. I like and am open to dating all races; however, white has always appealed to me more. The site I’m on, due to where I’m geographically located, has very few black women. And by few I mean for every 20 white women I see, I will see 1 black woman. That also tends to lead to more white women looking for white men, so I get it from both sides.

      I live in Arkansas, which is not known for it’s colorful surroundings like California or New York. Also, where I live, there are a large amount of women that are looking for “redneck romeo’s” which I’m very far from. I’m your city guy who loves to do city things. I don’t mind playing in the mud or riding horses on occasion, but it’s not something I would look to do more than two or three times a year.

      In a nutshell, dating is challenging and can be even more challenging depending on where you live and what you find attractive.

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      • avatar

        Elle January 11, 2012, 1:21 am

        Will.i.am, I feel for you too. When you’re in a place where you don’t exactly fit, it’s really hard to find the other person that’s a good fit for you. I am a city girl, and I was living in a rural part of upstate NY….

        I have to be honest – I don’t have a problem getting guys’ attention IRL. The problem is that most of them are 23. I don’t understand why more guys my age don’t approach me – or maybe I’m in the wrong place haha. And I think that, as a woman, I have it somewhat easier IRL – if a guy talks to me, all I have to do is reply. And I do reply – I’ll talk to everybody (young, old, male, female – I don’t discriminate!).

        Maybe talk to everybody you come across? See if you meet someone as receptive as I am? I did give my number to a few people I wish I hadn’t, but then again, not all bother to follow up. Some guys just want your number, but don’t want to see you again! I’ll never understand that, but to each their own, I guess.

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  • avatar

    AKchic January 10, 2012, 1:40 pm

    *hug* As a twice divorced woman, I do know what you’re feeling. Let me offer you some advice, one divorcee to another:

    1) Shave your legs for the first date. Be cautiously optimistic. You will feel more confident with shaved legs, and the date(s) may go better than they would have if you’d nixed the shaving that day.
    2) As long as the date is over 21, don’t worry about age too much. Seriously. Unless you look under 21, in which case, card them to be sure they are over 18. Age is just a number, so long as they can hold an intelligent conversation over drinks (whether it’s coffee or cocktails).
    3) Don’t worry about dating someone who knows a former flame. In small towns, it is inevitable. Don’t lie about your experience, but don’t get too detailed. Discussing the intimate details of past sexual experiences is only sexy if you’re discussing a lesbian three-way (and I’m only partially kidding here).
    4) Don’t take yourself too seriously. Have fun and remember that if you aren’t having fun, chances are, neither is your date.

    A divorce isn’t a death sentence.

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  • avatar

    Bossy Italian Wife January 10, 2012, 2:08 pm

    Divorce is a traumatizing experience in and of itself… so I am not surprised you are feeling this way. Wendy is right, you need to relax and have a little fun with it. If you can’t have fun with the experience of dating, or be able to laugh at your horrible sitcom dates, then the timing might not be right.

    Online dating in a small town, though, is awkward with a capital “A”–how do I know? My mother used to date online, and we live in a very small town. Her solution? She went outside the town. She dated people who live a state over sometimes, and while this can present challenges, it makes the pool bigger as well as providing a safe buffer. This might be a calmer and better solution for you as far as dating goes. Sure, you might drive a little more (or they might) but think of the benefits of never having to see the guy again if it doesn’t work out!

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  • avatar

    Miss Lynn January 10, 2012, 6:10 pm

    When I went through my divorce, even though I was the one who chose to end it, it still messed with my head for a good while. Its been 7 months since it’s been finalized and I only started really getting back into the dating scene a few months ago, so there’s no shame in waiting! Also, seeing a counselor really helped me get my confidence back as well, so there are always other options if you feel stressed about putting yourself back out there! Good luck!

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  • Amybelle

    Amybelle January 10, 2012, 6:32 pm

    I’ve tried online dating twice now since my divorce (about 2 years ago) Both times had a lot of anxiety/panic. The first time I thought maybe it was too soon, the next time was a few months ago; I know I’m “ready” so why the anxiety? I’m not a shy person at all and have no trouble talking to strangers. I have nothing against online dating, and it’s probably my best bet to find a guy. But that damn panic wouldn’t go away. Finally I decided to honor what I was feeling and just give up on the online thing. Someone up above mentioned some people just need to meet someone in person and I think that’s the case with me. All of the suggestions above are good, but it may be that online dating just isn’t for you, and there’s nothing wrong with that.

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  • fast eddie

    fast eddie January 10, 2012, 8:31 pm

    When I was dating the only line we had to be on was the telephone. You younger folks got it easier but the same issues exist and will continue to predominate as long as everybody seeks a companion. Reading between the lines it seems the LW has way high expectations of a date before going out with him. Ya gotta roll with the punches and let the date be a moment in time. My guideline then, and now remains, that anyone I want to share a part of my life with will have high goals and common values or there ain’t nothing gonna happen. Bottom line is relax a bit and have some fun without looking too far down the road. Try some other singles sites, okcupid allows anonymous browsing and makes suggestions all for free. I’ve made some friends there that I value greatly.

    A phrase I’ve encountered that reminds me of this situation: Walking about with a barricaded heart is worse than death.

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  • avatar

    Fast Charlie March 7, 2012, 11:02 am

    How bout dont get divorced?

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  • avatar

    Bob April 20, 2014, 11:51 am

    Your advice is pretty good, but as a guy who has been in 2 long term relationships with women I met online (4 years and my current gf of 1 1/2 years), I could write a book on this, but just let me add a few tips.

    (1) Don’t write a profile that tells me you’re funny, smart, interesting, yada yada yada. Write something funny, intelligent and interesting. If we’re guys you want to date, we don’t care about how great your job is, because we don’t expect you to support us. Similarly, if you need to know all that stuff about us, we assume you are expecting to be supported. If you’re truly independent, it doesn’t matter. I have never in my life asked a woman about her job nor worried about if she even had one. Why not? Because I don’t have to support her if I don’t wish to support her.

    (2) Talk to people and be friendly, even if you really don’t think you’ll ever go out with the person. You’d be surprised how much you can learn about how to talk to someone when it counts. Ditto for going on dates. Go on a few, that may be iffy. No matter how “bad” a date was, I always managed to find a way to at least make it enjoyable for the person I met. It’s called social grace and good manners. If you don’t practice, you’ll never be any good at it.

    (3) Don’t be a pain in the ass. The only guys who jump through hoops are those who are desperate. Be fun to talk to and find time to be online to talk to guys who interest you. I would think something as serious as a long term relationship ought to involve investing a little time. (If you’re too busy to check your messages everyday and reply to guys who interest you, you’re too busy for anything but casual sex, assuming that doesn’t require too much effort.)

    (4) If you want a second date, make sure they guy knows you’re interested in going out again. I never went on a second date with a woman who didn’t kiss me on the first date. You aren’t in high school anymore.

    (5) Don’t play games with sex. You’ll always lose, because having sex with the expectation of something in the future is just a losing strategy. Talk is cheap, so if you want to have sex with some guy, do it without expectations. If you can’t do that, don’t have sex and move on to the next guy. Assuming you like sex, there are worse things in life than having sex with Mr. Right Now who didn’t turn out to be Mr. Right. (I know that thinking tends to piss women off, but reality is what it is and reality always wins.)

    I could go on, but that ought to be a good start.

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