How to get up the courage to date?

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    So ive never really dated as such, my relationships have always come from friendships. Now i have been single for 4/5 years and am thinking I want to dip my toe in and see what happens. Ive been online dating for a bit and have a couple of guys I’d like to meet, we’ve discussed it, what we might do, the problem now is just arranging a date.

    This is where I go wrong though. Just the thought of it sends my anxiety through the roof and it puts me off going any further than chatting online or via text. I want to start very very casual because ive been single so long, i certainly dont want to rush anything but, for me, even one date is quite…. involved.

    All these thoughts keep going through my day like what do i do if i dont like him, or worse, what do i do if i do like him? Thta terrifies me that i might actually end up in a relationship, as much as i want to. I think part of me wants to sabotage this whole thing so i dont have to put myself out there and potentially be happy or get hurt again.

    And how do you go about dating more than one person? I need help!


    Hey lexy99,

    I have the same issues. I’ve been single for something like 7 years; last time I went on a date was probably 3 or 4 years ago. I’m still trying the online thing, but it seems the women that are interested in me are not women I’d be interested in, and vice versa. But the few times that it came to “where do we go from here” (i.e. “do you want to meet?”) I’ve felt the anxiety and written things like “just interested in discussing things” or something.

    I wrote that because I was doing what you describe: what-iffing. What if I hate her personality? What if I *like* her personality, and then I have to change my whole life to accommodate a relationship?

    Your what-ifs all seem to go down a fearful road. It may take some work, but can you replace the fearful what-ifs with positive thoughts about dating, even if you don’t believe the positive thoughts? Stuff maybe like “Ok, I just arranged a date, it makes sense that I’m afraid, but I can do this anyway, and I may even have a good time. At least I will have gone on a date. I can do this!”? Breathing exercises can help as well. Perhaps breathe deeply and think to yourself “I am strong. I can do this”? Making this part of a daily routine can really help; 2 months ago I was a disaster of hurtful emotions, and practicing what I just described as well as being in the moment helped tremendously…I still practice the breathing every night before bed. It’s easier now that it’s become routine.

    If you do like him, you can still take it slow if you want to. But I suggest that, when you make a date, you do your best to focus on the fact that you’ve accomplished making one date as opposed to worrying about what might happen afterward. From your words, it sounds like worrying is what you do and what you’re used to. When the worry thoughts come in (“what if I don’t like him, what if I do?”), try to let them roll or slide away from you. Maybe visualize the thoughts evaporating, and then replacing the thoughts with either being in the moment or with positive thoughts like “I can deal with that when or if it happens”.

    If you don’t like him, you can be polite at the date, and be assertive later (perhaps online) about how you don’t think it’s going to work out. If he brings it up mid-date, maybe say something like “I’m not sure how I feel about this. I need time to think about it” and get back to him later.

    Are you asking about dating more than one person because there’s currently more than one guy you want to date? Given the anxiety you have about one date, I’d take it slow and schedule one date. But if you want to do two dates, I think that’s fine; a date is not a relationship, you’re not beholden to anyone else.

    Hope this helps.


    Dear lexy99:

    Usually I do not have simple advice. Usually I venture into the person’s childhood to figure things out. This is different and I am almost excited about it- I have a simple advice which I practiced myself when I did online dating:

    Make a date in the daytime, Saturday or Sunday, in a coffee house, or a casual restaurant, perhaps outdoor: not a busy place but a place where you can sit with the guy for as long as two hours. As long, not necessarily as long. You tell the guy, kindly, that you will have to go back home after two hours. That is the time limit.

    After the date, at home, you can figure things out. Not under pressure, not during the date but after you are alone again.

    Do the same thing with another guy, two hours, not longer. Go home alone. Take it from there.



    Hi, thanks for your replies, they helped alot. I tend to overhtink things alot which makes things worse, I need to just bite the bullet and do it.

    And i like the idea of setting a time limit, having a ‘routine’ as such to simplify it all; go on the date for up to 2 hours, go home, think about it, go on another date.

    I also need to remember tht a date is just a date, nothing more unless im happy with that


    Hi lexy99,

    I truly think that within five minutes you can tell if there’s chemistry or if someone is normal/someone you’d like as a person. The thought of going on a date (even a coffee date) and him being a dud or weird would put me in a state of anxiety!

    I say go to events: plays, farmers markets, places of worship, parties (the grown-up kind with wine as opposed to beer), etc. Tell people you know that you are single. Let other people introduce you to someone. It’s safe because you’re within a group of friends. A certain amount of pressure is off. And it isn’t a “date” ~ you’re just being introduced at, say, an outdoor concert!

    Good Luck,


    • This reply was modified 8 years, 7 months ago by Inky.
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